At the start of my project, I was certain that I knew where I wanted to go. Was I ever wrong. This project has taken me in many different directions and has been a fun adventure from beginning to end. This project would not be possible without a culmination of people.

The first person I want to thank is my advisor, Professor Davarian Baldwin for agreeing to guide me through this process. Despite my constant use of the passive voice and some very poorly constructed sentences, you never gave up on me. So for that and so much more, thank you.

I want to thank my mom, dad, and brother, for always pushing me to be better than I thought I could be and never letting me get too down on myself. I would not be here today without all of you.

To Greg, Chuck, Phil, and Jake for believing in me despite constantly telling me that I would not finish my project in time. Trinity would not be the same without you all.

When I was stuck, Amina Kureshi sat with me and helped me reconstruct the overarching theme of my project.

Finally, I want to thank the Trinity College departments of American Studies and Economics for always believing in me while at the same time showing me how much more there was to learn. Over the past four years, I fell in love with both fields of study and built great relationships within the departments. There are too many spectacular professors in both departments to thank all of you by name but from the bottom of my heart, you are what make this the school that I love.


Introduction: “I’m Rick James, Bitch!”[1]

  • Dave Chappelle

Coming off of the second season of his hit comedy show, Dave Chappelle was being hailed by media sources around the country as “the funniest man on television.”[2] The Chappelle Show had found a way to revolutionize sketch comedy through creative yet taboo racial sketches. The show’s wild success was closely tied to the memorable characters, ridiculous stories and the quotable lines that were produced week after week. The Chappelle Show invented many characters that became fan favorites, such as the crack addict Tyrone Biggums, Clayton Bigsby, the blind black man who was a white supremacist, and his memorable quotes such as, “I’m Rick James, Bitch!”[3] In these sketches Chappelle captured both the absurdities and difficulties of navigating race and racism in our so-called post-racial America.

For two years, The Chappelle Show had reenergized Comedy Central by bringing a new look and a new audience to the network. “Chappelle ha[d] posted stronger 18-49 ratings than South Park in 11 of the past 13 weeks. Network research indicate[d] there [was] little duplication of viewers between the two shows and that “Chappelle” brought in new urban viewers while still retaining Comedy Central’s core audience.”[4] Over the first two seasons of The Chappelle Show, Chappelle had changed Comedy Central’s reputation from the network that showed South Park to become the “go to” station for comedic programming. The show’s “raucous brand of racially charged humor has made Chappelle the highest-rated original series on basic cable,[…] even topping South Park, Comedy Central’s highest-rated program for the past eight seasons”[5] During his contract negotiation before season three, Comedy Central offered Chappelle an unprecedented contract worth $50 million[6]. In a sudden and surprising turn of events, Chappelle walked away from his show and the money.

Soon after his rejection of the $50 million dollar deal, rumors started to circulate about Dave Chappelle. Entertainment Weekly (EW) posted an investigative report concluding that Chappelle had “flew from Newark airport to South Africa to check himself into a mental health facility.”[7]  Soon after EW posted their story, MTV, Today, and many more news sources had similar stories on their websites.[8] In a rapid media cycle, rumors about Chappelle circulated rapidly. Sources started recycling the theories and facts and bloggers began speculating wildly.[9]

According to Chappelle, he felt that his comedy was becoming socially irresponsible and that the executives at Comedy Central intentionally stonewalled him. After finishing up filming one day, Chappelle decided that he had enough and decided to walk out of the studio, never to tape another episode of The Chappelle Show again. Only telling his brother where he was going, Chappelle flew to Africa to clear his head.[10] Chappelle refused to talk to anyone outside of his family. Without rationale of Chappelle’s decision or any evidence of what he was up to, the media began to print a wide variety of stories with similar racial undertones.

EW, People magazine and seemingly every blogger started to declare that Chappelle had gone crazy. Some said he had a mental break-down and checked himself into a mental hospital while others were saying that he was addicted to crack and overly paranoid. The media started assuming the cause of Chappelle’s sudden disappearance was rooted in racist rationale. The accusations that the media leveled against Chappelle were similar to the very same clichéd stereotypes Chappelle had flirted with and critiqued throughout his show[11]. Chappelle had enough of the media twisting his meaning and when he returned from Africa, Chappelle took a break from public life.

As it turned out, Chappelle was not crazy or a drug addict. His departure was about the tightrope he had walked between racial commentary and comedic appeal. After a yearlong break from the public, the comedian broke his silence. In an interview with Oprah Winfrey, Chappelle said that he “felt like I was being deliberately encouraged to be socially irresponsible.”[12] He saw his show as a critique on black stereotypes where people could laugh at the absurdity and recognize the misconceptions that every black person in America was represented by a stereotype. Chappelle felt responsible for the reactions that his comedy was eliciting from white America. Chappelle came to the realization that his show was not improving the way that “post-racial” America views African Americans but reinforcing the racial tropes. Chappelle felt a moral responsibility to stand up for what he thought was right and he began to realize, his show was no longer sending the message that he wanted to send; so Chappelle walked away. Underneath the controversy of his departure lay an extremely complex comedian and comedic voice. ”What you laughing at” explores the nuance of Chappelle’s comedic voice as social commentary on institutional racism within the minefield of racial commentary and caricature in contemporary America.

After a decade long hiatus from public comedy, Chappelle began to perform stand-up comedy again.[13] He had returned, rededicated to the rejection of the perpetuation of racial inequalities. In June of 2014, Chappelle returned to the big stage by performing at Radio City Music Hall in New York City for ten straight nights, hammering basketball team owner Donald Sterling and southern cooking queen, Paula Dean[14] Chappelle mused, “[t]hey had a tape of an 80-year-old white man being racist…I did not see that one coming.[15]” It was his first major performance in eleven years. In 2015, Chappelle returned to feature film for the first time in 14 years where he appeared in Spike Lee’s film, Chi-Raq.

Chappelle used his voice to challenge audiences to see the world from his perspective and discuss the institutional repression of African Americans in American society. Chappelle’s show, in all of its absurdity and brilliance served as a conduit for his audience to navigate the construction of racism and racial difference in a society where race is being used as an evaluator of superiority. In all of its comedic wit and quickness, Chappelle’s show forced us to reconsider socialized notions of race by using the exact tropes and stereotypes Chappelle experienced. By portraying complex and poignant personal experiences through a comedic lens, Chappelle served as a platform where thoughtful conversations about race, racism, and their enduring persistence in a so called “post-racial” America occurred. Yet still, as Chappelle admitted, he felt “guilty for being asleep at the wheel”[16] while producing his show. He desired to maintain a socially responsible voice, falling victim to the same tropes and media-led oppression that he so frequently critiqued in his comedy. Chappelle unknowingly veered into reinforcing, rather than undermining, the socially constructed hierarchy of race in America. With the realization of the shows altered course, Chappelle reconstructed his own message, to recreate his criticism of racism and racial difference in America.

In order to fully examine the social commentary through his comedy, I survey two primary fields of scholarship. Cultural biographies of black comedians are critical for situating Chappelle within the history of African American artists that have used their platforms to make critical commentary. For example, in On the Real Side, Mel Watkins’ supports and contextualizes the evolution of opportunities for black comedians.  Biographies, such as Scott Saul’s Becoming Richard Pryor, gives a more detailed look at individual artists’ development. Using the biography of Pryor, along with those of Cosby and Paul Mooney helped to provide the context needed to address Chappelle’s style in popular American culture. These works were also essential for helping me to balance my attention on the artistry of a single comedian within equal attention to their social, political, and multi-media contexts.

However, while useful, these were biographical works were of comedians that came of age before the so-called “post-racial” era so their understandings of race and racism cannot attend to the particularities of Chappelle’s world. I was also able to survey works that examined the processes of racial formations after the Civil Rights era. For example, The New Jim Crow: Mass Incarceration in the Age of Colorblindness by Michelle Alexander and George Lipsitz’s, Possessive Investment in Whiteness, weave the timeline of the evolution of racial formations from slavery to the present. This body of scholarship allowed me to navigate claims of “post-raciality” with analysis that detail the evolved articulations of race and racism in the period so formative to the life and artistry of Chappelle. Yet, these works do not fully engage the complexities of popular cultural as a site where contemporary racial formations can be explored. By bringing together cultural biography and scholarship of racial formations, this project will offer a fine-grained examination of race and racism through the lens of a single comedian and the world that he navigated.

In my project, I analyze the comedic work of Chappelle through close readings of sketches from The Chappelle Show, historical analysis of racial context, brought together through a cultural biographical approach. I look at specific sketches from The Chappelle Show, his comedy specials, journalistic accounts of Chappelle life, interviews, and the film Dave Chappelle’s Block Party to argue Chappelle’s struggle to maintain his voice as a vehicle of social commentary.  These sources provide the ability to understand Chappelle’s intent and contrast it to his audience’s reception.

Chapter one focuses on the development of Dave Chappelle’s voice as a critic of racial formations. The chapter focuses on discovery of the interconnectivity of comedy, culture, and race in America. Chapter two explores the success and failures of The Chappelle Show in regards to viewership and Chappelle’s ability to convey his criticisms to America. Chapter three analyzes Chappelle’s reconstruction of his image and voice after his messy departure from The Chappelle Show and mainstream America.


Chapter 1: “It’s like the Race card. You’re so worried about it. I am worried about how in the hell did it get in the deck”[17]

-Paul Mooney

Years before most people would know the name Dave Chappelle, he was a young comedian, trying to convince television studios that he was funny. In 1991, Chappelle began his career in the comedy clubs of New York City where he began to find success. He had some minor achievement writing for television shows and playing small roles in various films. Eventually Chappelle got a meeting with Touchstone production executives about a sitcom he wrote and was to star in. With his agent, Chappelle flew out to Los Angeles from his father’s house in Ohio.  The pilot episode was inspired by his first stand-up performance at the amateur night at the famed Apollo Theater in Harlem, New York. As Chappelle recalls, he looked into the crowd at the end of his performance, he saw “like everyone booing. I mean everyone. Even like old people. Who boo’s a child pursuing his dreams?”[18] The pilot episode of the sitcom was focused on that performance and starred an entirely black cast. Chappelle was excited to tell his story, but when he walked into the office of the Touchstone executives, Chappelle felt that something was not quite right.

As Chappelle started discussing his ideas for the show, he started to hear buzz words being tossed around that concerned him. He kept hearing these executives talk about “universal appeal” and “diverse draw”[19]. These terms were politically correct ways for the executives to tell Chappelle that they wanted to include more, white cast members. Chappelle did not want to throw white people into the show just to appease the network. In Chappelle’s experience, there were no white people at his first performance at the Apollo Theater, so why should they be in the pilot episode?  Chappelle did not want to white-wash his show, even if it meant that the network would not pick it up.

The network executives and Chappelle were unable to reach an agreement about casting for the show, ultimately leading to the network’s choice to pass on production. The next day, as Chappelle traveled back to his home in Ohio to visit his ailing father, he noticed a Variety Magazine cover that called out Chappelle for playing the race card to try and get his way.[20] As one of Chappelle’s biggest idols[21] Paul Mooney would later comment, “You’re so worried about [the race card]. I am worried about how in the hell did it get in the deck.”[22] The magazine blamed Chappelle for the show not being picked up rather than touchstone and FOX for their insistence on whitewashing Chappelle’s sitcom. Chappelle responded to these accusations. He countered, “They fly me out for a creative meeting. I’m in a room full of white people, and they proceed to tell me why we need more white people on the show, so it can have a more universal appeal.”[23]  The network claimed that they wanted to pick up a show, but only if it could have a wide appeal. Chappelle protested that people did not love Eddie Murphy, Bill Cosby or Richard Pryor just because “they’re surrounded by white people, Cosby only had white characters when it was feasible, and nobody noticed.”[24]  For the first time in Chappelle’s career, he felt as if his attempts to do the right thing ended up being misrepresented to the American public.

Chappelle entered Hollywood with a clear idea of how he wanted his voice to influence his audience. He had spent years watching other influential black comedians, such as Richard Pryor and Eddie Murphy to hone his craft. He saw their comedic brilliance and their incorporation of social commentary as corner stones of their artistic voices. Chappelle’s career was barely off the ground but he faced a tough decision. Would he make a sacrifice and cast white actors or refuse to compromise his vision.  Chappelle set the precedent from early in his career that he was going to fight to keep his voice as a vehicle to serve as an analog to explore the absurdity of the culture of racism in America. Chappelle witnessed the complex ways that racism disguised itself in American society throughout his life. He picked up on subtleties that few others did and expressed those insights through his comedy to anyone listening.

Dave Chappelle was born just outside of Washington DC on August 24th 1973. The youngest of three and grew up with highly educated but divorced parents. His mother, Yvonne Reed had a Ph.D. in African American Humanities and was a professor at Howard University. His father, William David Chappelle, was a statistician and later became a professor at Antioch College in Ohio. Chappelle grew up in a time where racism evolved from explicit legal and cultural restrictions to a more coded and nuanced set of unspoken but clear understandings of social difference.  Even before his lifetime, racism had begun to hide in plain sight.

In the mainstream media, America is often referred to as a post-racial society. Wanting to believe that this is true, many Americans choose to accept this notion without questioning it. According to a Pew Research center poll, 50% [25] of Americans believe that America is post-racial. The common rhetoric is that after the Civil Rights movement in the 1960’s, America has been able to move past its history of slavery and oppression of people of color. Many argue that since slavery was outlawed and Civil Rights laws have been put in place, America has been able to fully heal these wounds and repair the inequalities created by a strong racist past.

Before Chappelle was born in 1974, the boundaries of racial discrimination had started to blur. Highly visible forms of discrimination such as separate water fountains, fire hoses, and burning crosses started to fade but racial discrimination hid itself in the fibers of American society. After World War II, veterans returned home and the GI bill provided many with benefits, including low interest mortgages, loans and financial support and purchasing a home had never been as accessible. Veterans were being helped to buy a home; a huge source of generational wealth in family. But black veterans were excluded from the benefits of the GI bill. Because of the way the bill was written, the federal government did not oversee the process of home loans, business loans, or college payment. The black veterans returned from World War II and were refused loans and rejected from all white colleges. In New York and northern New Jersey,

“fewer than 100 of the 67,000 mortgages insured by the G.I. Bill supported home purchases by nonwhites. […]The University of Pennsylvania, along with Columbia the least discriminatory of the Ivy League colleges, enrolled only 46 black students in its student body of 9,000 in 1946. The traditional black colleges did not have places for an estimated 70,000 black veterans in 1947.”[26]


The GI bill had created a form of racial discrimination that was harder to see for the average person. Such institutional racism stemmed from the nuances of how the laws were written and enforced. With the GI bill alone, the black veterans were unable to get an education, unable to purchase a home or start a business at the same rate of their white counterparts.  All of these factors helped to reduce the amount of wealth that they could pass on to black families and their communities.

Throughout the 1950’s and 1960’s the more direct and easily visible forms of racial discrimination were torn down piece by piece, yet other racial barriers were constructed out of sight. After the Civil Rights act of 1964 and the Fair Housing Act of 1968, the letter of the law stated that all people had the same right to vote, to housing, regardless of their race. The American public wanted to believe that they were in a post racial era after the Civil Rights victories. In the 1970’s, under President Richard Nixon, many of the Civil Rights acts that had been signed into law stopped being enforced.[27] When tested, under the Nixon administration, the integrity of the Civil Rights acts was not protected. It was illegal to discriminate in real estate based on race, but when instances of racial discrimination occurred there was a dearth of government enforcement. The lack of enforcement set the precedent that as long as the perpetrator did not commit blatant offences, they would not be prosecuted. Real estate agents started heavily using this to their advantage. Black people were legally refused housing in suburban communities under the excuse that their presence would lead to housing price decreases.[28] Residential exclusion drove the black population into the inner cities where renting was much more common. Meanwhile, the white population had moved to the suburbs and primarily bought homes, leading to a white racial consolidation of wealth rather than a democratization of public and private resources.

Racially discriminatory practices helped to create a massive re-segregation of residency and resources with racial minorities in impoverished inner cities and the white population kept in prosperous suburbs. White families would commute into the cities and at the end of the take, take all of the income out of the city. Rather than spending the money in the city which would lead to a larger tax base and a larger flow of income, the money was leaving the local economy. Fiscal divestment led to the devastation of largely black and brown central city neighborhoods that gave way to the so-called “ghettoes” of today[29]. The schools in the inner cities became severely underfunded and extremely segregated. In cities, there are still school districts that look like Brown v. Board of Education never happened.

The more blatantly racist policy of redlining in the 1950’s evolved into racial steering where real estate agents chose to not show homes to Black and Latino families because the area was located in a primarily white area. These policies helped to maintain segregated neighborhoods and prevent any forms of redistribution of wealth while becoming a more coded racist system.

Opportunity to create wealth was stripped away from the black community; all while many Americans remained blissfully ignorant of the racism occurring around them. But racism in the housing market was not the only way that racism hid itself in modern society. Starting with the Rockefeller Drug Laws in 1973, the war on drugs established minimum prison sentences for drug possession and sale. One year later, Dave Chappelle was born on the outskirts of Washington DC. The narcotics with the toughest penalties were assigned to drugs like crack cocaine, which were primarily used by black people while powdered cocaine, more frequently used by white people, was punished less heavily. The government used fear tactics to convince the public that America needed to be harsher on “inner city” drugs in order to protect their children. Major faces of the government came out in favor of these bills. While she was the first lady of the United States in 1996, Hillary Clinton labeled groups of young black children “the kinds of kids that are called super predators. No conscience, no empathy.”[30]   The American public became terrified by the black community. Because of the fear mongering rhetoric that was being peddled by the American government, the legislation in regards to drug policy was severe. These new laws began to target black neighborhoods.

Chappelle’s mother lived just outside of Washington DC where he attended the local elementary school that was not very diverse. Dave started his schooling with a rigorous academic environment at home. In his interview on Inside the Actors Studio, Dave recalls doing “very poorly. I never liked school from the first day I walked in and said I hate this place.”[31] Dave did not find the same level of interest in academics as his parents hoped that he would. Dave was a highly intelligent student with little desire to devote his energy towards school. He started to explore other interests. Chappelle learned from his parents that no matter what he chose to do, he had to be smart but his parents were unable to convince him to use his intellect in his highly segregated school environment.

During his middle school years, Dave’s mother Yvonne moved into the northwest of Washington DC. Chappelle remembered that “the neighborhood was wild and I was just at that age where I would want to start running the streets so to speak.”[32] His mother determined that this was not the environment she wanted Chappelle and his siblings to grow up in. As Dave entered middle school, his mother sent them to live with their father who had moved to Yellow Springs, Ohio. Yellow Springs had a population nearing 5,000 people and was quite different from where Dave had spent the majority of his life up until that point.

Considered to be predominantly a “hippie” town, his father was engaged at the time in a human rights organization with the primary goal of ending racism. At this point, Dave began to notice how race played a role in the communities where he had lived. Yellow Springs was a small community so Dave could develop a picture of the larger town. He began to compare Ohio with his experience living in Washington DC. He saw how economic inequality impacted the city’s black community. Dave would later develop his comedic voice, using these experiences to help him understand how race shapes not only perceptions but opportunities in a society that claims to have overcome a history of racism.

While Chappelle was in Ohio, the crack epidemic exploded in Washington DC.  The city that he had known changed immensely. When Chappelle returned to the city for high school he witnessed the immense harm that the crack epidemic was having on youth in the black community. Between classmates dropping out to sell drugs and the little that anyone was doing to try and help the community, Chappelle had a hard time adjusting to the city life after coming from Ohio. Chappelle contrasted the lives of his family and his community in both Yellow Springs and Washington DC and saw a massive divide between the quality of life in a primarily white middle class area and Washington DC in the midst of the crack epidemic. Living with his mother during the school year and spending the summers in Ohio with his father, Chappelle began to develop a unique perspective on race and race relations in America.

For those that did not have the same role models at home as Dave did or the opportunity to move out of the cities, the path to success was more treacherous. Dave was lucky to have his mother sacrifice being able to see her children every day to offer them a better chance at opportunity.

Dave was struggling to adjust back to Washington DC after the explosion of the crack epidemic. He was seeing the way that the “wild”[33] city was impacting the greater community. A big moment in Dave’s life came when his mother bought him an edition of Time magazine. The cover of that edition was “Cosby Inc.”  with the caption “funny, famous, fifty – and Really Rich”. In this edition, Chappelle read about Bill Cosby and his highly successful career as a comedian and actor. After reading the magazine Chappelle believed that he could be a comedian. Dave sat his family down to break the news to them but to his surprise, he received overwhelming support from everyone. To start understanding the life of a comedian, Dave started attending stand-up shows at local comedy clubs. At only 14 years old, Dave was denied entrance into many of the local comedy clubs because he was too young to enter a venue that served alcohol and the content was considered too risqué for a minor. He needed a legal guardian to enter the comedy clubs. After pleading with his mother, Chappelle convinced her to chaperone him on week nights. Even when his mother was busy, Chappelle convinced his grandmother, to accompany him to these clubs to watch the comedians.

Every weekend Chappelle would collect a little bit of money and go to the local comedy clubs and watch the live stand-up comedy. Talking with James Lipton on Inside the Actors Studio, Chappelle told the audience, “Live comedy is the most incredible thing in the world to me. Like the first time you see a dude just standing there. Talking every joke he’s saying just hitting and working. Every weekend, I’d go”.[34] Seeing a comedian captivate a crowd mystified Chappelle. Dave went so frequently that the people working at the clubs started getting to know him. He just sat there week after week observing and laughing. On the weekends, he took notes on the strengths and weaknesses of different comedians. As he befriended one of the comics at the club, Chappelle received the advice to take start taking acting classes. Having trouble adapting to his new high school, Chappelle transferred to the Duke Ellington School for the Arts where he graduated in 1991.

Growing up in a largely black city facing re-segregation, municipal divestment, and the criminalization of youth, Chappelle was witness to the effects that these processes had on the population of Washington DC. Moving to a more socially liberal area in Yellow Springs Ohio, Chappelle observed that segregation was not a naturally occurring phenomenon; it was created by society.  Seeing the massive segregation in his home city, juxtaposed to the situation in Yellow Springs, Chappelle grew up with a perspective that few had. Chappelle saw comedy in the fact that people who did not suffer from the issues of segregation even denied the existence of racial inequality. By growing up in both the highly segregated Washington DC and the liberal Yellow Springs, Ohio, Chappelle could precisely pick out the differences in the way people behaved and were perceived differently for the same behaviors.

Chappelle honed his craft for hours on end, using a candle stick as a substitute for a microphone and a mirror as his audience. Dave slowly worked up the courage to start performing[35]. He prepared a short routine for the open mic night at one of the comedy clubs he started frequenting. In stand-up comedy routine that he wrote, Chappelle attacked the hypocrisy of America pretending to be racially blind but in reality was racially biased. In his first routine, Chappelle talked about what would happen if the Muppet alien Alf landed in a primarily black neighborhood rather than a white suburban one.[36]

He saw that television shows presented to children were not reflecting his reality but were so heavily catered to the white audience. As a black child having seen the differences between childhoods in a primarily white versus black area, Chappelle used his time on the stage to talk about the inconsistencies. Alf claimed to be a television program with universal appeal but in reality the show helped to perpetuate the white supremacy through subtle means. Chappelle saw the segregation and took it from an unspoken idea to the front and center for his audience. Chappelle was developing a unique voice, based in poignant critiques of the effects of race and racism in America that would eventually carry him into millions of homes around the world. As his audience grew, his ability to comically render the subtleties racial inequality improved.

He idolized Bill Cosby, Richard Pryor, and Eddie Murphy and began practicing his stand-up comedy routine day and night.[37] Chappelle analyzed their styles and tried to take the qualities of their comedy that he liked and use them to craft his own style. When Chappelle went to an Eddie Murphy stand-up performance, he was amazed by his opening act, Paul Mooney. Chappelle quickly learned more and more about Mooney’s career and discovered that Mooney wrote the famous SNL sketch where Richard Pryor stood up to a white interviewer during a job interview. Chappelle recalled seeing a black man hold his own on television, which “gave me the direction my life was meant to go in.”[38] Mooney quickly joined the ranks of comedy inspirations.

In his comedy, he offered poignant critiques that many people saw but few people spent significant time pondering. Drawing from Pryor, Mooney and Murphy, his comedy routines focused on the themes of the interconnectivity of racial identity and difference in America and African American culture. Chappelle drew from these inspirational comedians to begin shaping his comedic voice as one that would help audiences rethink status quo ideas about racism, racial stereotypes, and inequality in America. He began performing all around Washington DC and after graduating from high school, he relocated to New York City. New York City was the epicenter for comedic success, kick starting the careers of many comedians before him, including Pryor, Cosby, Murphy, and Mooney.

Race and racism were taboo subjects. It is difficult and uncomfortable to confront one’s own socialized beliefs without feeling like they have done something wrong. People do not want to talk about how much money they make with the people they work with. Even if a black worker performs the same tasks as a white worker, on average they make 75 cents on the dollar.[39] I believe that most Americans do not support this pay gap but feel like they do not know how they can change anything. It was in tackling the unspoken and the taboos where Dave Chappelle so adroitly used his comedy as a tool to open the dialog and facilitate change. His ability to take on multiple perspectives with his audience allowed him to relay the impacts that modern day racism can have on the society as a whole. Through laughter, Chappelle created agency for those that have been disenfranchised to talk about issues that impact them but others do not see. In a 1993 performance in Montreal, Chappelle joked, “I got lost today. The POLICE helped my find my way!”[40] He was surprised that the Canadian police would help a lost black man. Without saying it, he pushed the audience realize that in America, the results may have been different. From everyday life, concerns about social interactions and even talking about the way movies portray individuals.

After being booed off the famous Apollo stage, Chappelle walked away with an ironic feeling of relief. This situation, perhaps his worst nightmare, did not really faze him: “That night was liberating because I failed so far beyond my wildest nightmares of failing, that it was like, Hey, they’re all booing, my friends are here watching, my mom, this is not that bad, and after that I was fearless.”[41] After his experience at the Apollo Theater, he was able charge ahead. Chappelle had the confidence to tell new jokes and try out new delivery styles. He was able to develop as a better comedian because he was not worried about audience rejection. As a comedian, he felt confident and ready to hone his craft and develop his unique style.

Touring around New York City, Chappelle was able to break into the comedy club circuit. He began to draw a buzz around the city and quickly built a reputation as a young up and coming comic. Suddenly, all the clubs wanted him to perform at their venues. Chappelle remembered as his reputation grew, all the club owners started talking to one another. They started asking one another “”Have you seen this kid? Have you seen this kid?’ I was like that dude.”[42] Performing all over the city, he gained attention from comedians, television producers, and filmmakers. As his popularity rose in the New York Comedy scene, Chappelle was offered a role in Mel Brooks’ film Robin Hood: Men in Tights. Chappelle was becoming a recognized presence across the country which ultimately led to a film role alongside one of his idols and major comedic influences, Eddie Murphy.

Chappelle recalls his experience working with Murphy on The Nutty Professor as the one that pushed him to be a better comedian. Chappelle fondly recalled his time working with his childhood idol as, “the best feeling, like, to make Eddie Murphy break character was very– to this day, man, forget the Emmy nomination. That was like… that was the best.”[43] Eddie Murphy pushed Chappelle to write more comedy for television and film because as Chappelle remembers Murphy telling him, “’You gotta start writing. The way you tell jokes, you think in pictures, and you can write. You should start doing it,’ and that was big.”[44] Murphy’s advice was a revelation for Chappelle because he had not really considered writing a feature film before.

Over the next year, Chappelle and a friend of his, Neal Brennan, got together and wrote the script and created the film Half Baked. The film became a cult classic in the genre of “stoner movies”. Chappelle is now known for his racial commentary in The Chappelle Show, but this early work was far more focused on general male hijinks and buffoonery. At the time, Chappelle’s screenwriting style resembled that of a stoner frat boy more than that of Eddie Murphy or Richard Pryor. Chappelle wanted to focus on improving his style to be more in line with the comedian he wanted to be. Chappelle believed that “the script was way better than the movie”[45] but as it went through production the studio began to change the film into a different type of project. Instead of making an adult comedy, the studio wanted a larger target audience so they made the film more “kid friendly”. To Dave’s dismay, this would not be the last time that a studio altered the message of one his works, leading him to appeal to a different audience than he would have preferred.

In 1998, Half Baked was released and grossed $17 million at the box office[46]. But then, on his 24th birthday, Dave received a call from his sister. His father had a stroke and over the course of the next year would slowly pass away. While at home, taking care of his ailing father, Dave received the call from Touchstone about purchasing the sitcom that lead to Chappelle being accused of playing the race card superfluously. Chappelle decided that he had enough and left Hollywood to take care of his father. In a conversation with his father, they discussed what it meant to be successful in show business. Dave’s father told him to “name your price in the beginning. If it ever gets more expensive than the price you name–get outta there.”[47] The cost for Chappelle had become too high. He was commuting from California to Ohio and back so frequently, he grew fatigued. After a few months, Dave’s father passed away. His father’s passing was very hard on him, marking his “father’s death in 1998 as the beginning of a terrible decline”[48]  Losing one of his closest friends and confidants, Dave felt alone. He felt beat down and misunderstood. Chappelle decided that show business was costing more than it was worth and bought a farm in Yellow Springs, Ohio. Chappelle felt ready to retire from show business but before long, he would be lured back.

After a short hiatus, Chappelle was offered a stand-up comedy special with HBO. He had changed his style from half-baked, putting more emphasis on nuanced jokes with subtle meanings than the more ham handed juvenile shtick he had written for Hollywood. Jumping at the offer, Chappelle taped the one-hour special, Killin’ Them Softly.[49] The special became a hit and Dave was hailed by the audience[50], the media[51] and his fellow comedians[52] as one of the funniest men in America. In an interview with GQ, Kevin Hart, recalled how he and “Chris [Rock] were joking about how Dave was just so much better than us — the thought process behind his jokes. How he makes it look effortless… He’s in a different realm. He’s out of this world, man.”[53] Chappelle approached comedy in a way few were able to. He did not achieve the same level of popularity but his jokes were as creative as anyone else’s. The special explored the aura of the hood at night, police brutality, and foul mouthed, drug dealing toddlers.

Dave’s comedy drew attention to the divide between perception and the realities of African American life. In one of his jokes, Chappelle is sitting in a limousine alone, in the middle of the ghetto. Chappelle quickly locks the car doors and keeps a vigilant watch as he waits for the driver to return. Chappelle noted in his interview on Inside the Actors Studio, “Listen, man, black people don’t like the ghetto.”[54] Chappelle reacted to his situation the same way the audience would expect a white person to behave. The joke illustrated the intersection between race and class as a wealthy black person performed stereotypically “white” behaviors by locking his car doors and jumping at sudden noises in a way that challenged a strict alignment between blackness and comfort with danger. His HBO special put Chappelle in the position to make a big impact with a large audience. Chappelle swung for the fences and with a combination of creative jokes and pointed commentary on racial foundations, for the first time he showed the public his matured voice.

Dave started to become very popular for his unique style of comedy. His jokes satirized the generalizations and stereotypes that people make, specifically about African Americans, and highlighted the absurdities that underlie them. Through his jokes, Chappelle showed the intersectionality between the issues of class, race, and gender in present day America. Taking themes from Richard Pryor, Paul Mooney[55], and Eddie Murphy, Chappelle’s comedy offered a critique of a modern America, identifying that society had reverted back to ignoring the issue of racial disparities and double standards while identifying people of color based on racial stereotypes. He prided himself in being able to offer sly social commentary through the double entendre. The double meaning of racial caricature and anti-racist critique was clear to Chappelle when writing his jokes but to the audience that did not share his experiences, the critique could be missed. His jokes made people roll on the floor laughing but in the back of their minds the audience started to explore the basis of the joke. The ability to offer trenchant social critiques wrapped in over the top frat boy humor or irreverent racial stereotypes made Chappelle a comedic force to be reckoned with.

Chappelle furthered his fame when he took a role in the 2002 satirical film Undercover Brother. He played “Conspiracy Brother.” This character’s identity was centered on the stereotypical black community figure that goes beyond calling out systematic racial injustice to the point of seeing all acts and ideas as part of some larger racial conspiracy. In one of his very first scenes in the film, Chappelle goes on a tirade about the original, racist meaning of the phrase “Good Morning” as part of a system of oppression that the white man uses to keep black people down. Throughout the film Chappelle goes off on what are perceived as ludicrous rants. Chappelle had hoped the film would be a big success but only grossed a disappointing $39 million in the United States box office[56].

The audience laughed at the absurdity of the conspiracies that Chappelle’s character holds until the joke, is in fact, turned back at them when the characters discover that “the man” is, in fact, attempting to use a genetically altered fried chicken recipe to control the minds of the black population. The style, which at the time was becoming classic Chappelle humor, showed the absurdity of mainstream media’s representations of African Americans, especially when offering a critique of systemic oppression in America. In some regards, claims of racism had become the punch line in post-racial America, the joke was any claim of racism at all. But Chappelle went further by using the very stereotypes now deployed to dismiss racism to highlight the persistence of racism in America. Chappelle’s ability to turn a joke back onto the audience themselves and question their own beliefs was special and Comedy Central saw the value of his signature style.

In 2003, Dave Chappelle and Comedy Central worked out a deal and began production on The Chappelle Show. He finally had a platform that held an unprecedented level of creative control[57] with a show that could present his comedic voice to a wide audience. Chappelle had developed his voice as a tool to highlight and refute racist notions of racial difference that were hidden in the so called “post-racial” American society. He had big plans for his show and the resulting work would go on to have a big impact on Chappelle.








Chapter 2: “The worst thing to call somebody is crazy. It’s dismissive.”[58]

  • Dave Chappelle

The laugh. The wrong type of laughter. The moment for Dave Chappelle where he realized it had gone so wrong.

In between seasons two and three, Chappelle had just signed the biggest contract of his life. Between a long and hostile negotiation with Comedy Central for his new $50 million contract and the stress and workload that the show put on Chappelle; he was already feeling overwhelmed. Working with Neal Brennan and the rest of the show’s writing team, Chappelle was recording the new sketches for the upcoming third season of The Chappelle Show. He was on his way towards becoming one of the biggest stars in Hollywood. Starting the new season, Chappelle was looking to continue the show’s success. One of the sketches for the start of season three was about racial groups altering their behavior to avoid confirming racial stereotypes. In the sketch, it shows four different racial groups being confronted by choices to make a decision that they desired but would in fact conform to a racial stereotype. While facing these decisions, they are confronted by a pixie played by Chappelle himself. The pixie, dressed as a racially stereotypical blackface character, attempts to entice the person to make the decision that would align with the stereotype.

The sketch opens with a professional Dave Chappelle on an airplane, reading a magazine in his first class seat. The stewardess approaches Chappelle asking if he would like the fish or the chicken. Suddenly the pixie, also played by Chappelle , appears on top of the seat[59]. Dressed and acting as a caricature of a subservient black bellhop at the turn of the 20th century, the black faced pixie tries to persuade Chappelle to order the chicken rather than the fish. The first-class passenger Chappelle is uncomfortably aware of the stereotype that black people love fried chicken and thus chooses to order the fish instead. The stewardess comes back to tell Chappelle that they are out of the fish, giving his character another opportunity to fill the stereotype. Chappelle then asks how the chicken is prepared and it is, of course, fried. The black-faced pixie celebrates as Chappelle, with disappointment in his voice, orders the fried chicken. Throughout the sketch, the pixies try to entice members of various races to fill the stereotypes that society holds for those groups. For Chappelle, it was the black man ordering fried chicken, for the Hispanic man it was buying leopard print seat covers, and for the Asian man it was mispronouncing the “L’s” in someone’s name as an “R.”

On the surface, these jokes were funny but were devoid of the social commentary that accompanied Chappelle’s other flirtations with racially clichéd stereotypes. Something was off. Instead of taking these racial stereotypes and highlighting the absurdity, Chappelle was almost reaffirming the truth of stereotypes. In his previous sketches, Chappelle would bring the trope to the focal point and create a situation in which the audience had no choice but to reject the validity of the trope. In this sketch, Chappelle showed people of color naturally desiring to behave in a stereotypical manner but resisted the behavior to avoid others judgement. I claim that the nuanced critiques that Chappelle had become famous for were nowhere to be found in this sketch or the rest of the third season. The show had drifted from its message and Chappelle came to that very realization when he took a step back just before season three was about to premier in a few weeks.  Chappelle did not want to be just another Hollywood star, implicit in the systematic repression and stereotyping of minorities. He did not want to sell his conscious for the fame and fortune. Chappelle had drifted so far from his message from the beginning of the show and without his own realization. His voice had changed, but how did he get to that point?

Comedy Central picked up The Chappelle Show with the hopes that it would be able to diversify their audience base. Comedy Central was not the network it is today. When he first arrived, “It wasn’t like comedy central was a hot place to be”.[60] Chappelle wanted to use his creative freedoms to make the show what he wanted. Working with Neal Brennen and Paul Mooney, Chappelle wanted a show where “they could tell shit jokes” as well as make serious social commentary.

The show became a major hit. Sketch comedy had a new bar set by Chappelle, Mooney, Brennen, and the rest of the show’s team. Critics around the country praised the innovative and original style of the show. Linda Stasi of The New York Post said the first season was “genuinely ingenious, and hilariously outrageous – not to mention courageous. Plenty of people will find Chappelle’s Show offensive – but then again, whenever you do something completely new, it’s bound to offend somebody. In this case, it will offend a lot of somebodies.”[61] Chappelle and his team were writing shows and sketches that refused to back down. The sketches in the first season did exactly as Chappelle had hoped.

The sketches combined over-the-top hilarity with racial humor that attacked the deep rooted seeds of racism corrupting American society. Between the sketches “Ask a Black Dude” in which strangers on the street could ask Paul Mooney about any black stereotype they wanted; “Frontline: Clayton Bigsby” the story of the white supremacist that was unaware that he himself was black; to the sketch in which black people were paid reparations for slavery, The Chappelle Show  undermined racist institutional formations.

In the fourth episode of the first season, Chappelle offered a sketch in which America paid black people reparations for slavery. The sketch opens on a newscast with the lead anchor being played by Chappelle in white face. Chappelle informed the audience that congress had passed legislation to pay African Americans reparations for slavery and the checks had been delivered that morning.[62] Chappelle sends the fake news cast to a reporter on the streets of Queens, New York to see the impact that the money was having. The reporter is standing in front of a line of black people waving their checks at the camera. The camera pans out as the reporter introduces herself to reveal that the location is in front of a liquor store. At this point, the audience starts to see where Chappelle is going with the sketch.

The reporter goes around interviewing some of the people that are willing to talk with her. Approaching a man driving up in a truck, the reporter asks him if he is considering quitting his job as a truck driver now that he has received his reparations check. The truck driver responds, letting the reporter know that he is not a truck driver; rather he took his reparations check and bought a truck full of cigarettes; enough cigarettes for him and his family for the rest of their lives. The sketch shows characters conforming to the extremes of the racist tropes that mainstream America holds. These characters take the money they are given and rather than using the money responsibly, they spend it in a frivolous and stereotyped manner. Chappelle shows the people throwing their money away on alcohol and driving trucks full of cigarettes and “bling”. Chappelle takes these racist tropes and over exaggerates them in order to highlight the absurdity in which they are based.

The first scene of this sketch highlights exactly the type of comedy that made Chappelle’s Show as successful as it was. Chappelle introduces his sketches with a vague premise that gets the audience to start thinking about race; in this situation, the United States government paying reparations for slavery. The audience, unaware of where Chappelle is going with it, is drawn in with the ideas already churning in their minds of how black people would respond if they were given reparations. The thoughts that a lot of people have are that they will respond with senseless spending. Immediately, Chappelle goes over the top with the stereotypes of alcohol, cigarettes, and gold chains that many people think about African Americans but refuse to say publicly.

After the report from the street however, the newscast goes “from Beat Street over to Wall Street”. The show dives straight into a mock stock market report about the impacts of black people having money has on specific sectors of the financial markets. The financial correspondent opens by noting Sprint’s stock price had jumped with two million delinquent bills being paid. Going straight from Sprint, the correspondent announces that gold and diamond prices are at an all-time high. Both the joke about Sprint phone bills not being paid and the record prices for gold and diamonds reflect the unspoken assumptions the media portrays about the black community. At the time, Sprint was a cheap cellular alternative to AT&T, Verizon, or Singular and it attracted a lot of minority subscribers.

Chappelle wanted to take these assumptions that the mass media made about black society, that they do not pay their phone bills and love gaudy jewelry and confront them head on. While introducing the sketch, Chappelle talked about how reparations money would be needed to reinvest into the community. But by showing this reaction, the reaction of the population spending on themselves wastefully, Chappelle forces the audience to confront the presumption that these stereotypical behaviors are naturally occurring in the black population. At the same time, while white America scoffs at perceived black consumption habits, the quick shift to Wall Street demonstrates the connections between black purchasing habits and the wealth created in mainstream financial markets. He forces the audience to confront their own ideas and creates an opportunity for the audience to reject these beliefs themselves. At the same time the comedy speaks to a black audience that assumes such depictions as stereotypes as thus automatically read the “joke inside the joke” from the start. Throughout the rest of the sketch, Chappelle continues to highlight the divides between the racially charged beliefs held by many and the actual overlaps between black and white worlds.

Noting the spike in fried chicken prices to over $600 dollars a bucket, eight thousand record labels opening, and three million Cadillac escalades sold, the white reporter jokes that black people were trying their hardest to give back the money. These stereotypes are rarely directly said but are subversively present in many forms of actual media.  Chappelle brings these unspoken presumptions into the public forum. By putting these ideas on the main stage of his show, he is able to use his voice to condemn these beliefs as anything more than fiction; all while creating unique and original comedy. At the conclusion of the first segment, the audience has been shown these over-the-top representations of a stereotypical black community. Chappelle has made joke after joke, critiquing the way the black community is represented as a whole at the end of the episode; Chappelle brings back the news report to show how a black man is represented in the mass media.

The second part of the sketch opens with an interview with the world’s new richest man. The man who overtook Bill Gates as the world’s richest man is Tron, a Harlem resident who gained his fortune through six straight hours of a lucky hand at a dice rolling game. Bragging that he is now the world’s richest man, he declares “and I’m Black!” highlighting the idea that it is strange that a black man could be in his position. Played by Chappelle, Tron is asked what he is going to do with the money. He initially states that he is going to reinvest into the community and once the white female interviewer, representing pure and innocent white society, starts to praise Tron on his good will, Tron reveals that he was joking. Chappelle does this to create the comparison between what people should do and what a black man is expected to do. Chappelle exposes this gap by taking these thoughts and overplaying them. Throughout the interview, Tron continues to overtly flirt with the interviewer, reinforcing societal norms of an oversexed black male image, while the interviewer is slightly aroused by his wealth. Chappelle’s show juxtaposed Bill gates and the fictional character Tron to show the difference in expectations that America has for a white and black man with wealth. Chappelle’s voice cut through the racist tropes and left his audience laughing while at the same time rethinking their internal racialized views.

Sketches like “Black Reparations” pushed the show to draw huge audiences and reshape the image of Comedy Central. The show was credited “with raising Comedy Central’s black audience from 7 to 20 percent.”[63] In the coveted 18-34 male demographic[64], the show drew “more…viewers than any TV show.”[65] After the first season finished, the boxset went on sale and quickly became the highest selling in television history[66]. Comedy Central started to develop its most diverse audience ever. The large ratings were originally thought to be overflow from South Park aired before it but as more research was done, the audience had very little overlap. While Chappelle found great success in the show, it came at a cost.

Chappelle attempted to renegotiate his contract after the first season but with little luck. He had one year left on his two year deal which forced him to settle for less than he wanted. The network made Chappelle demonstrate that the show would continue its success before giving out a large contract. Chappelle complained that “I ain’t makin’ no money!”[67] Despite the historically large viewership and DVD sales, Chappelle did not believe that he was earning proportionately to what the network was making. The negotiations were not pleasant and he ultimately settled for less money than he had wanted. At the start of the second season, Chappelle began to notice some changes that made him uncomfortable.

Throughout the second season, the network tried to take more creative control and gave more notes to Chappelle on which jokes they thought should be cut and which ones should be used. The executives wanted to control Chappelle and use his show for their own interest. In his interview with Oprah, Chappelle, “felt in a lot of instances I was deliberately being put through stress because when you’re a guy who generates money, people have a vested interest in controlling you.”[68] A lot of the notes were encouraging Chappelle to move away from his critiques of American culture, pushing to have his jokes appeal to a wider audience, racially coded terminologies that mean make his content more suitable for a white audience. The season began to take a large toll on Chappelle. As the second season continued, Chappelle became fatigued and felt over-worked. The continuous pushes by the network to change his comedic style to improve ratings started to wear him down. I believe that as Chappelle became tired over the course of his show, he was unable to focus on carefully crafting each sketch such that his sly commentary on racial stereotypes lost their focus and shows began to move away from the message that Chappelle wanted to pass along without him even noticing. After walking away from the show, Chappelle told Oprah that, “I wasn’t paying attention. I felt really guilty for being asleep at the wheel.”[69] Chappelle unknowingly let his voice waiver under the pressures of his own expectations, the network executives, and the fans. The audience of The Chappelle Show grew to record highs by the end of the second season. The show achieved greater success with respect to viewership but to Chappelle, the moral standard of the show regressed.

The regression of Chappelle’s voice is clearly seen in some of the later sketches of season two. In the eleventh episode of the second season, Chappelle featured a sketch titled “In a Gay World”[70]. The sketch was based on a hypothetical situation that all of the gay people in America segregated themselves into their own civilization. The sketch opens in a very similar way to that of the black, blind, white supremacist. In a fake Frontline report, the sketch shows what gay America would look like. The sketch showed what a gay DMV worker, a gay landscaper, a gay Klu Klux Klan member, and even a gay boxing match would look like. In each of these situations, Chappelle plays off of a different stereotype, following the mold that he had set throughout the show. But this time, it was different. This sketch did not critique the stereotypes that portrayed. This sketch does not change the perspective of the audience. The sketch highlights the notion that if gay individuals were allowed to redefine society, they would choose to be more flamboyant and society would devolve overall. Chappelle consistently had trouble expressing socially acceptable commentary on issues that were deemed lesser by his heterosexual, masculine lens; specifically gender and sexual inequalities. In this sketch, his blind spot is revealed but because of the stress and slipping of his voice, Chappelle still deemed the sketch as acceptable for his audience to watch. This sketch does not try to influence positive change in the social conscious. This sketch is different from what became Chappelle’s standard social commentary.

The sketch, “In a Gay World”, reinforced rather than rejected stereotypes. As The Chappelle Show was wrapping up its second season, these sketches that failed to live up to Chappelle’s social conscious became increasingly frequent. The lures of maintaining ratings had begun to overshadow his desire for his show to have a positive impact on his audience. As Chappelle stated in his interview with Oprah, he was stressed out and facing a lot of pushback from the executives at Comedy Central. In his interview with Oprah, Chappelle said, “I got fluttered with things and you don’t pay attention to things like your ethics”[71] Chappelle had let his voice falter without even realizing it. The voice Chappelle so confidently used in the first season of his show began to falter by the end of the second season. The difference between the social critiques that he made in his sketches was grand. The contrast between the black reparations sketch and the “In a Gay World” skit show the wavering of Chappelle’s voice.

After the second season, Chappelle began renegotiating his contract, but this time he held all of the cards. The show had transformed Comedy Central from the channel with South Park to the network where people went to watch comedy television. The second season averaged 3.1 million viewers per episode and when the box set went on sale, it had the largest opening sales ever with 500,000 copies sold within the first weekend.[72] The viewership of Comedy Central had exploded and the show had rebranded the station. Network President Doug Herzog stated that “There’s no question about it, [Chappelle] was the hottest thing on the network.”[73] Chappelle had worked the second season on a contract he believed to be below market price for the reception his show was receiving.

Going into the third season, Chappelle prepared for a long negotiation. He knew that Comedy Central could not afford to lose him. Bill Hilary, an executive vice president and general manager of Comedy Central at the time, acknowledged that the negotiation was not going to be smooth. He said to reporters, “Is it going to be a tough one? Yes. But I think Comedy Central is the place for Chappelle.”[74] The sides started negotiations with a wide gap between what Chappelle wanted and what Comedy Central was offering. Chappelle’s demands were not limited to a raise. He wanted a larger share of DVD sales and was looking to get Paul Mooney his own comedy show that was based off of the show Jude Judy.[75] Comedy Central was hoping to limit Chappelle’s share of DVD sales, seeing those as huge profit centers and were concerned that a show hosted by Mooney could alienate fans. Chappelle always believed that “Paul Mooney was too black for Hollywood” and they were afraid of what he would say.[76]

After an ugly renegotiation process, the new deal was announced and Chappelle was about to become one of the highest paid actors in television. The comedian was set to earn $50 million over two years. The contract made headlines around the world. The hard work that Chappelle had put in was finally going to literally pay off. However, going into the third season of Chappelle’s Show, Dave once again noticed a shift in the way he was treated by the network executives. After the tough negotiation, Chappelle believed that the executives wanted to make Chappelle look weak. So as the third season got delayed for a variety of reasons, there were suddenly articles appearing in The New York Post and The Pittsburgh Gazette blaming Dave for the delay because he was struggling with Pneumonia[77] and simultaneously other media outlets claimed the delay was due to writer’s block.[78] Dave was confused about why these stories were being printed because he felt fine and had not even begun writing the third season yet. He felt like the executives were trying to manipulate him and put him in a compromised position. They came to him and asked him “Dave can you back up the pneumonia story?”[79] and Chappelle did not want to. They had made up the story without Chappelle’s consent and he had no desire to help them out with it.

Working on the third season, Chappelle became exponentially more stressed than he had been before. People were trying to convince Chappelle that he was going crazy and that he should start taking antipsychotic medication[80]. Chappelle had just beaten the house. He had used his cutting social observations to become one of the most famous people on television and the network was trying to take away his power. Chappelle believed that the network executives were just trying to make him look like just another crazy black man that made his way into Hollywood.

The intended reception for the show was to bring universally known but rarely talked about racial stereotypes and generalizations to the forefront. Chappelle underscored the absurdity of the arguments that differences were naturalized in the race of individuals. Chappelle had tried to use his voice to make a positive impact on those around him and his audience. But by the end of the second season, Dave saw the audience take his jokes not as a rebuke but in fact as proof of the racist stereotypes many held.

In the “Pixie” sketch that Chappelle was filming for the start of the third season, he started to notice the effect that the comedic racial tightrope he walked was having on the audience. At one taping he watched the way one observer laughed and it gave Chappelle chills and made him feel completely isolated.[81] On his interview with Oprah, he said, “I felt like there was a deficiency in Vitamin love.”[82] The environment around the show had changed and had become toxic. He felt that the sketch was socially irresponsible and it authorized people to confirm their beliefs about the truth of racial stereotypes rather than highlight the absurdity behind them.

Taking his father’s advice, the cost of the work had begun to outweigh the rewards. In a shocking decision, right before the third season was set to premier; Dave Chappelle decided to walk away.
















Chapter 3: “I like entertaining. And the higher up I go, for some reason, the less happy I am!”[83]

-Dave Chappelle


Chappelle needed to clear his head and relax; telling no one besides his brother[84], Chappelle just left. As word spread of Chappelle’s disappearance, wild rumors began to circulate. These rumors were not contained to just tabloids. The rumors spread around the mainstream media viciously with stories that would ultimately prove to be pure lies. News reports, similar to those Chappelle believed had been spread by the Comedy Central executives, started to come out. The reports had claimed that Chappelle had gone crazy and that he was a drug addict. MTV reported[85] that he was in a mental health facility and Newsweek announced that Chappelle had become addicted to crack cocaine. The media accused Chappelle of being a crazy black man, the exact type of racist assumptions and stereotypes that Chappelle had criticized over the duration of his show. Chappelle was unwilling to deal with the tone-deafness that the media had developed towards black entertainers.

While in South Africa, Chappelle started reading these articles and wondered where the media was getting their stories. He had not talked with reporters and the only person that knew what he was doing was his brother, who had not been linked to any of the stories. Chappelle saw the media saying “’I don’t understand this person, so they are crazy.’ Its bullshit. These people are not crazy. They are strong people. Maybe the environment is a little sick.”[86] The media had not even given Chappelle a chance to speak before twisting his words for their own cause. He felt betrayed and intentionally sabotaged. His voice, which he had carefully crafted throughout his life, had been corrupted and was no longer serving as a tool to improve social conditions. Instead the audience was looking at Chappelle himself and questioning his sanity.

When Chappelle came home from South Africa, he decided to try to take a break from his public life. He moved back to Ohio and wanted to spend time with his family. Chappelle slowly tried to clear his head but he became paranoid. Walking down the streets, he swore that he heard “somebody yelled out, ‘Gumbel!’ I turned around, and no one was there. It was a sniper slur. That shit bugged me out!”[87] The stress that he had gone through had made Dave paranoid. Chappelle decided that it was in his best interest to start publicizing his side of the story. Chappelle set up various interviews to try and get his message out into the public. In these interviews, Chappelle tried to explain his rational for leaving but also took the time to clear the air that he was not crazy or a drug addict.

In February 2006, Chappelle went on an interview tour to clear up the reasoning behind why he left The Chappelle Show. Even after his interviews on Oprah and Inside the Actors Studio, Chappelle was struggling to get his message across to the public. Whenever talking to a news outlet or magazine, Chappelle felt that there was not an effort to understand him. He started to feel that “people around you position themselves around you, to get in your pocket and in your mind”[88] To Chappelle, his fame had become an avenue for others to gain wealth and popularity. The people surrounding Chappelle saw his comedy as a tool they could use to improve their own lives. Chappelle told Oprah that he was willing to consider coming back to the Chappelle Show to finish the third season under a few conditions. Chappelle wanted to do his show again. He wanted to ensure that he could “make the proper work environment”[89], Chappelle would maintain complete creative control of the product and that half of the back end profits would go to charities. At the time Comedy Central had announced that they would be showing the unaired sketches from season three, also known as “The Lost Episodes of The Chappelle Show.” Chappelle firmly stated that he would not come back if the episodes were released. Comedy Central quickly stopped promoting the lost episodes but ended up releasing them anyway under the same format of The Chappelle Show, this time with Donnell Rawlings and Charlie Murphy as the hosts.

From the experience pitching his sitcom to the Touchstone executives to the third season of The Chappelle Show, he was always careful about the type of people working around him.. Charlie Murphy, Paul Mooney, Donnell Rawlings, and his longtime friend Neal Brennan were pulled in to participate in The Chappelle Show because they shared similar opinions about the type of message to craft. Their diverse backgrounds but common goals created some of the most iconic sketches of The Chappelle Show. Their ability to work in tandem brought together ideas to create the sketches such as “Real Hollywood Stories with Charlie Murphy”, the “Player Haters Ball” and “The Race Draft.” As The Chappelle Show gained popularity, the core group was pulled apart. Some of the sketches created by Rawlings, Brennan, and Murphy were becoming recognized and attributed to Chappelle. Chappelle was gaining fame and fortune because of their ideas. When Chappelle decided to walk away, he also sacrificed the avenue for Rawlings, Brennan, and Murphy to develop their own careers.

While Chappelle had the fame and agency to pursue other opportunities, Murphy, Rawlings and Brennan did not have the same level of independence. The show’s success had not made them household names in the same way that would allow them to pursue other opportunities. Their success was tied to the show. Without The Chappelle Show, Charlie Murphy would go back to being Eddie Murphy’s brother. When Comedy Central approached the trio to help out with the lost episodes, Rawlings and Murphy saw an opportunity to maintain their fame. Since Dave had just left without communicating his intentions to the rest of his team, they were left trying to maintain the venue that had cultivated their success and the executives new this.

Rawlings and Murphy agreed to cohost the lost episodes in Chappelle’s absence. In an interview with G4, Rawlings explained, “I’m a loyal person, but I know that as a professional, I’ve got to keep my career going, and I felt it was an opportunity for me, for people [to] see what I do as funny… without knowing what Dave Chappelle’s agenda is, the reasons why he left, with no communication saying, ‘Hey guys, I feel this way. I would much rather you not be a part of this process.’ Had I had a conversation with Dave like that then there’s a possibility that I would reconsider me hosting it.”[90]  Instead of believing that Chappelle had made a conscious decision to not show the unaired sketches from the third season, Donnell Rawlings and Charlie Murphy put their career first and chose to host three episodes of the “Lost Episodes of The Chappelle Show”. Chappelle was once again unable to control the message that his show was sending to the audience. With the pixie sketch, Chappelle originally used the black face because it was going to be the physical embodiment of the n-word but what he did not consider was that “the way people use television is subjective.”[91] People look to television for their own purposes and can take whatever they want from it, not only what the creator intended.

Having brought the cast together, Chappelle was upset and disappointed that Comedy Central, Rawlings, and Murphy had decided to continue the show despite his objections to the third season being aired. Chappelle was willing to go back and fix the third season “provided that he could make the proper work environment.”[92] Chappelle had come to the realization that much of his voice had been caricatured by his white audience and it had been re-appropriated to for uses that he did not intend. He wanted to be socially responsible. Chappelle said “I don’t want black people to be disappointed in me.”[93] Rather than listening to the sketches and reevaluating their own racialized beliefs, the white audience took the racial caricatures on face value, as depictions of racial truths. In his open letter to his white fans, Chappelle stated, “You wanna know why I went to Africa? Because “I’m Rick James, bitch!” was becoming the new “Dy-no-mite!”[94] Chappelle referenced the white laughter at “JJ” Jimmy Walker’s patented phrase from the 1970s hit Good Times, to show how racism had perverted his comedy as well. By playing a black crack addict defecating in the street, the audience was receiving the message crack addicts defecating in the street was a “black” thing.

Chappelle did not want to be the person that told the white audience it was okay to re-appropriate the black experience, let alone caricatures of the black experiences. His voice failed to maintain the social impact that he had intended. Disgusted by the way he was treated when he left the show and with the way that he was treated when he returned from South Africa, Chappelle decided that he had enough of public life for a while. He was worn out. Chappelle did not want the general public to know where he was or harass him at all. He needed time to reconstruct his own image in a way that he deemed acceptable. Dave needed a break.

Chappelle rejected all offers he received to appear in films and television shows for over a decade. He wanted to go back to the relationship between himself and the audience directly in front of him. Chappelle did not want his voice to be to be mediated by other opinions. He also was concerned with maintaining the creative integrity he had cultivated with a multi-racial, but largely black, collective of artists, activists, and intellectuals put on display in the musical interludes of his show and showcased through his iconic documentary Block Party. Chappelle had tried to do what he considered to be the right thing throughout his career and he needed to take a step back. For his own well-being, Chappelle decided to leave the mainstream in order to reconstruct himself. The experience gained from his show taught Chappelle a lesson that he would hold onto for a long time. He learned how seductive and persuasive the mainstream media was when inside of it. By taking time away from show business, Chappelle was able to reevaluate the path he was taking.

The first step was to alter his aesthetic style that was attracting the drunken frat boy following that he had started to grow so frustrated with.[95] In his letter to his white fans, Chappelle said “maybe you saw in Block Party where Questlove from The Roots was talking about how frustrated I was with the “demographic” I attracted after Half Baked. That demographic, white people, was you.”[96] In his open letter to his white fans, Chappelle stated that he could not “stay in a relationship that’s always challenging my dignity and integrity. That’s Wayans Brothers territory. But I do realize that I’m partly to blame; skits about piss and venereal disease are just begging for a frat boy following. That’s why I’m turning over a new, socially responsible leaf.”[97] Chappelle made it clear that going forward, he was not going to spare his white audience’s feelings. He would perform the material that he wanted to perform and it would be material that he felt comfortable putting out into the world.

Chappelle not only wanted to reconstruct his voice. In his absence from public life, Chappelle also reconstructed his physical stature, destroying the physical resemblance to the characters he portrayed in his show. Chappelle no longer desired to be able to play the role of crack addict, Tyrone Biggums.  He began to work out and became much more muscular. His newly created muscles helped Chappelle to break away from his previous life. Going forward, when the audience would look at Chappelle, he would not just be seen as the same person that played the characters from the show. He would be the new Dave Chappelle.

For the first few years of his sabbatical, Chappelle sporadically showed up to comedy clubs. He attempted to avoid his fame while satisfying his love for performing comedy. Instead of chasing viewership or ratings, he went back to the performance genre that he fell in love with as a child. Stand-up comedy enraptured Chappelle and it is where Chappelle felt completely in control.[98] Chappelle told whatever jokes he wanted to tell and did not need to answer to anyone but himself. His voice was not being heard by as many listeners and he was not making as much money but he had full agency over his set, unlike in his days on television.  According to Kevin Powell of Esquire, Chappelle “doesn’t like to feel, as an artist, as a comedian, as a black man in America, like he is being controlled — ever.”[99] The freedom that came with standing in front of a live crowd and making them laugh was unlike anything else to Chappelle. Without any formal notice, Chappelle would show up to a comedy club. Sometimes it was in New York[100], sometimes it was in San Francisco.[101] He took control of his life and tried to avoid the circus that came from people knowing where he was going to be any given time. By only performing stand-up comedy, Chappelle could see how the audience received his jokes and could determine where to go as the performance progressed. He could play along with a good crowd and he was able to walk away from a bad one. He had reclaimed his body and voice. But as an artist, the desire for total control, a resistance to the dialogue with the audience, can come with consequences both good and bad.

For the good and the bad, Chappelle gave himself the power to decide the course of each performance. He began to slowly rejoin the mainstream comedy circuit. Going on tours, working with booking agents and agreeing to be hired for causes, Chappelle reintroduced himself to the public with caution to not repeat his previous mistakes. In 2013, Chappelle had joined the Oddball Comedy Tour. This comedy tour traveled the country with many famous comedians. On August 29th 2013, the tour came to Hartford, Connecticut[102]. At this show, Chappelle experienced an audience that was openly hostile to Chappelle’s refusal to use material from The Chappelle Show. Rather than let him perform his routine, the audience began to yell some of the most famous catch phrases from The Chappelle Show and heckled the comedian as he waited for the audience settle down.[103] The disruptive audience did not allow Chappelle to perform his routine.  Chappelle refused to perform with the audience behaving this way and after a few minutes of unrelenting interruptions, Chappelle walked off stage. He refused to accept anyone but himself dictating his performance. Word of the Hartford show quickly spread. The media caught on and Chappelle did not mince words about his dissatisfaction with Hartford.

In an interview with Slate, Chappelle talked about the complicated relationship between the white audience and a black performer. From Chappelle’s recount, the audience was full of “young, white alcoholics” that were “suburban torturers”[104]. Chappelle did not want to fill the role of the black entertainer to a white audience. Chappelle refused to let this audience dictate to him what kind of performance to give. After the performance, Chappelle told Slate that he, in reference to the racial outburst of Seinfeld actor Michael Richards “wanted to, like, pull a reverse Kramer and call ’em all crackers or something crazy like that.”[105]  Chappelle wanted the crowd to respect his creative direction but the audience had trapped Chappelle in their own caricature: the famous characters from Chappelle Show. But Chappelle wanted to control his own life and did not care if it made the audience, especially a predominately white audience, unhappy. After the crowd continued to yell at the stage, Chappelle walked off, not even getting the chance to start his performance.[106]

Chappelle faced a significant amount of fall out for walking off the stage in Hartford but remained consistent with his new direction. He wanted to be able to control the message that he was putting out into the world and had enough experience with outside forces trying to take his voice from him. Right before walking off stage in Hartford, Chappelle said to the audience “‘Hey, I just want to do my jokes.” As the crowd kept yelling at Chappelle to do the jokes they wanted, Chappelle refused. He responded by saying,

“Ah, fuck you. I’m the one that has to get the review in the paper tomorrow. I’ll have to read about this shit for months. And the next time, I go on television and they interview me and they say, ‘Why’d you go back to Africa?’, I’m not gonna say Hartford did it.”[107]

Chappelle wanted to be seen as a person. The comedian would not let his audience tell him what jokes to tell. He would not yield his new voice for anyone. Chappelle refused to allow the Hartford crowd to tell him what jokes to perform. He did not hate his audience; he did not hate the people that loved the Chappelle Show but to Chappelle, being able to control his voice was the most important thing.

Even after swearing that he would never return to Hartford, for a show, or even for gasoline for his car, Chappelle relented. In a surprise appearance on the one year anniversary of the Hartford performance, Chappelle appeared as the closing act of the 2014 Oddball comedy tour in Hartford. In his performance, Chappelle made it clear that the blame for the performance the year before was on the crowd but he still showed the fans his appreciation for continuing to support him: “Are you sure this is Hartford? I swear to God I thought you were going to boo me the minute I came out.” Chappelle joked, “Boy I wish you guys were here last year”[108] Chappelle liked to control the message of the show but he still wanted to redeem himself. He admitted that “It was a year ago tonight; I had 364 nights to think about that fatal night, one year ago. … I was really immature about what happened.”[109] Chappelle wanted to make his audience laugh and by coming back to Hartford, he could show that he was willing to move past transgressions if the crowd would forgive him. The crowd quickly cheered and Chappelle went into his routine. And he didn’t perform one character from Chappelle Show After talking about his experience selling shirts that said “fuck Hartford” on his website; Chappelle dove right into a social commentary on racial difference in America.

Chappelle had set out to create a show in which he was able to make the comedy that he loved while maintaining a social responsibility. He recognized that with his fame came a sense of duty to be a role model for his audience. Chappelle wanted to help the people watching him to become better people and more racially sensitive. Trying to maintain that level of responsibility while become more famous proved to be impossible for Chappelle. He found that as he become more popular, he lost some of his creative control. He saw how ratings and money changed his perspective. Chappelle decided that he would not be able to live with himself had he sold his conscious. He did not mind losing the mass audience because the benefits vastly outweighed the costs. Chappelle had to lose control over his voice to discover how important it really was to him.

Chappelle uses his various platforms to highlight many of the complex and highly coded forms of institutional racism. He gave many a comedic roadmap to navigate racism within a so-called “post-racial” society. Like Richard Pryor before him, Chappelle look introspectively at his own experiences and tapped into the moments where he recognized contradictions within himself. In all types of media, many black performers share similar experiences facing coded racism throughout their careers. Chappelle built his community of musicians, comedians, and actors that helped him survive in the public eye.

In Dave Chappelle’s Block Party, he brought together a cast of amazing creative types from Common, Kanye West, The Fugees, Talib Kweli to The Roots, Jill Scott, Dead Prez, and many others. The common element was that all of these artists and activists were those that Chappelle both loved and admired, people who used their black creativity as a venue for discussing social issues and imaging a community where racism was made irrelevant. In Block Party Chappelle said that for “All these people, before I ever met ‘em, I was fans of theirs.”[110] Having messages that are similar to his helped Chappelle focus on the goals he set. From walking away from his blockbuster television show to the present day, Chappelle focused on creating a diverse community of performers that worked within a similar social-creative nexus. Before the 2016 Oscars, Chappelle and the host Chris Rock were together, prepping the now infamous opening monologue[111] that called out the academy for its institutional racism amidst the anti-racist campaign #OscarsSoWhite[112] Chappelle received help from his community and was ready to offer support in the face of collective struggles.

Chappelle’s entire career has been a struggle to walk the comedic tightrope between the desire to make people laugh and his insistence that people also think. Chappelle loved to be on stage and help his audience have an enjoyable time but the hoops Chappelle was being forced to jump by Hollywood and Comedy Central took a large toll on him. When his father was in his final days, he gave Dave some advice that if the cost of performing ever became more than the rewards he was getting, it is time to walk away. Throughout his career, Chappelle has followed that advice. When he was being pushed by network executives to white wash his sitcom, Chappelle found the cost to be greater than the reward of having his own show so Chappelle walked away. When he was being pushed off of his message during the end of The Chappelle Show, the cost overtook the benefit, and he left to Africa.[113] When the white audience in Hartford tried to bully him into performing their favorite characters from Chappelle’s Show, he walked off the stage. Going forward, Chappelle has taken a firm grasp of the cost of performing. He appears intent on keeping his hold to his integrity and does not appear to be letting go any time soon.





On August 23rd 2014, I was at the Oddball comedy tour at the Xfinity Theater in Hartford, Connecticut. Having driven up from Westport, Connecticut with my friend Jason, we were excited to see the all-star cast of comics advertised for the festival. Louie C.K., Aziz Ansari, Sarah Silverman, Amy Schumer, Dave Attell, and Hannibal Buress were set to perform. On the drive up, we were talking about which comedians we were most excited to see, which of the comedians we thought were going to be the best, and which other comedians we wanted to see in the future. At the top of my list was Dave Chappelle.

I knew that in the previous Oddball Comedy tour, Dave Chappelle was booed off stage in the very same theater. I had a few friends who had gone to the show and said that it was very disappointing. I did not care. As the videos started to surface on the internet, I thought to myself I would be upset too if people would not shut up and let me perform.  I thought that Chappelle was the funniest comedian I had ever heard. I had watched The Chappelle Show for as long as I could remember and had many of the sketches memorized from start to finish. Countless hours of my life had been spent on YouTube watching and re-watching Chappelle’s stand-up routines. So the top comedian I wanted to see live was Dave Chappelle.

With little jokes here and there, the performers kept poking fun at the city of Hartford, alluding to Chappelle’s performance from the year before. Aziz Ansari quipped that he would not start his performance until the crowd was quiet, almost an exact quote from what Chappelle had said in his now infamous performance. As the night went on, the show had great performance after great performance. All the comedians had lived up to our expectations. As the last comedian, Louie C.K., was wrapping up his performance, large parts of the crowd started to head for the exits to try and avoid the traffic. After telling his last joke of the night, Louie said, “and now let me present, Dave Chappelle!” In a collective gasp, the audience was stunned. The lines heading for the exit halted and everyone turned back to their seats. Chappelle came onto the stage and it was clear that he was a little nervous about returning to Hartford. Before he was able to start the room was loud. But this time, it was because there was enough applause and cheering that the building was shaking. Chappelle was able to quiet down the crowd and start. His routine was classic Chappelle. In his comedy, Chappelle seamlessly tied together jokes about his hatred for Hartford; his experience getting in a fight with a lesbian woman that he thought was a man, and the intersectionality of being a black gay man. To me, it was Chappelle at his best.

Through his show and his stand-up comedy, Chappelle played a major role in my life. In the community where I grew up, I was constantly told that “sure, there are some racial inequalities but they were not that significant and most people over played their impacts.” As I grew up, my parents always told me that I should never blindly take an answer without questioning it first. I thought that the best way to understand someone is to try and see the world from their lens. So throughout my life, I was always looking for ways to get other perspectives. When I started watching Dave Chappelle and his show, I laughed to the point of tears multiple times but I also began to question why he was making the jokes that he did. His comedy helped me witness the bigotry and intolerance that people of color deal with on an everyday basis. Over the past few years, we have clearly seen institutionalized racial inequality rear its ugly face through multiple different venues. With the targeting of minority populations with subprime mortgages, violent policing practices, and the re-segregation of schools, racist institutions in America are not in the past. Dave Chappelle takes a hard look at the roots of these controversies and uses his voice as a comedian to start the uncomfortable discussion on race that America tries to avoid.

Chappelle never became famous for his stand-up comedy. His live material may not be delivered with the same artistry as some of the other popular comedians but his material is some of the most creative out there. Chappelle’s ability to take the unspoken thought after a racially charged moment and bring it to the heart of his joke made his comedic mind as unique as any other. Chappelle used his creativity to not only change the way sketch comedy was used for social commentary but also change the entire model of sketch comedy. Since Chappelle left Comedy Central in 2005, the model of his show has remained the standard for sketch comedy shows. Over the past decade, Comedy Central has launched numerous projects that were not only made possible by the economic success but also mimic the style of The Chappelle Show.

Chappelle opened the door for Amy Schumer to start her sketch comedy show, Inside Amy Schumer, which offers stylistically similar comedic commentary on women’s issues in America. Chappelle’s success as a black actor appealing to a large and diverse audience also helped Key and Peele get the opportunity to make their show into the success that it is today. Key and Peele have acknowledged Chappelle’s influence and inspiration in the creation of their show[114], even though their show is very different in style from Chappelle’s. Dave Chappelle’s legacy as a sketch comedian helped to open the door for many others to follow. Thus, Chappelle will not go down as the best comedian ever or even the most influential but his ability to make his audience stare directly at the ugly truth of racial formations in American society through his comedy makes his story one that needs to be heard.




















My guide to the location of each sketch inside each episode of The Chappelle Show. Y denotes possible importance to my project, N – denotes no importance, No letter means possible importance.  










2/3/2006, Jennifer Vineyard. “Dave Chappelle Comes Clean On ‘Oprah.’” MTV News. Accessed April 17, 2016.

5/16/2005, Gil Kaufman. “Dave Chappelle Speaks: ‘I’m Not Crazy; I’m Not Smoking Crack’.” MTV News. Accessed March 23, 2016.

30, Bradford Evans August, and 2013. “Dave Chappelle Was Heckled and Walked Offstage Last Night in Hartford, CT.” Splitsider, August 30, 2013.

account, Chris Rock Verified. “Pregame #Oscars #DaveChappelle” Microblog. @chrisrock, February 29, 2016.

Andrew Wallenstein Hollywood Reporter. “Dave Chappelle Inks $50 Million Deal.”, August 3, 2004.

———. “Money Talks in ‘Chappelle’s Show’ Universe.”, April 19, 2004.

“An Open Letter From Dave Chappelle to His White Fans.” PopMatters. Accessed March 23, 2016.

Chappelle’s Show. Accessed April 2, 2016.

“Chappelle’s Show – Season 1 Episode 4.” Black Reparations. Comedy Central, February 12, 2003.

“Chappelle’s Show – Season 2 Episode 4.” Comedy Central, n.d.

“Chappelle’s Show – Season 2 Episode 11.” Chappelle’s Show. Comedy Central, March 31, 2004.

“Chappelle’s Show – Season 3 Episode 2.” Chappelle’s Show. Comedy Central, July 16, 2006.

“Chappelle’s Show: The Lost Episodes.” Accessed March 26, 2016.

Dave Chappelle. Dave Chappelle – Killing Them Softly ( COMPLETE ). Accessed January 22, 2016.

“Dave Chappelle (Ft. James Lipton & Students of Pace School of Design) – Inside The Actor’s Studio Interview.” Genius. Accessed March 30, 2016.

Dave Chappelle: Killin’ Them Softly. Accessed March 30, 2016.

“Dave Chappelle Kills at First Radio City Gig.” Rolling Stone, June 19, 2014.

“Dave Chappelle Performs to Benefit Cringe Humor Show Creator Masavia…” Getty Images. Accessed April 3, 2016.

“Dave Chappelle Returns To Hartford, Performs Before Supportive Crowd.” Tribunedigital-Thecourant. Accessed March 30, 2016.

“Dave Chappelle Walks Off Stage in Hartford.” NBC Connecticut. Accessed March 30, 2016.–221744821.html.

Davis, Tamra. Half Baked. Comedy, Crime, 1998.

Gilman, Azure. “Explaining the Black-White Wage Gap.” Freakonomics, October 6, 2011.

Hannah-Jones, Nikole. “Segregation Now …” The Atlantic, May 2014.

Harris, Aisha, and Matthew Dessem. “Dave Chappelle Turns Hartford Incident With ‘Room Full of White People’ Into Comedy.” Slate, September 5, 2013.

———. “How Much Do Chappelle’s Show and Key & Peele Have in Common, Really?” Slate, February 18, 2015.

Hontz, Jenny. “TV’s Race Card.” Variety, July 8, 1998.

Inside Actors Studio with Dave Chappelle. Talk-Show, 2008.

Just For Laughs. Dave Chappelle Stand Up – 1993. Accessed April 4, 2016.

Kotz, Nick. “‘When Affirmative Action Was White’: Uncivil Rights.” The New York Times, August 28, 2005.

Lipsitz, George. The Possessive Investment in Whiteness. Temple University Press, 1998.

Michel Gondry. Dave Cappelle’s Block Party. Rogue Pictures, 2006.

Mooney, Paul, and Dave Chappelle. Black Is the New White, n.d.

Moss, Corey. “Dave Chappelle Reportedly In Mental Health Facility.” MTV News. Accessed January 22, 2016.

“Mrs. Clinton Campaign Speech – Super-Predators.” Accessed March 27, 2016.

“Oddball Comedy & Curiosity Festival.” Funny Or Die. Accessed March 23, 2016.

“On the Beach With Dave Chappelle.” Time, May 15, 2005.,8599,1061415,00.html.

Oprah. “Chappelle’s Story.” Accessed January 22, 2016.

———. Dave Chappelle on Oprah – Why He Left. Accessed January 22, 2016.

Powell, Kevin, and 2006. “Heaven Hell Dave Chappelle.” Esquire, April 30, 2006.

“Punch Line Comedy Club – San Francisco, CA ::” Accessed April 3, 2016.

Saul, Scott. Becoming Richard Pryor. Reprint edition. S.l.: Harper Perennial, 2015.

Semuels, Alana. “White Flight Never Ended.” The Atlantic, July 30, 2015.

“Star’s Illness Delays ‘Chappelle’s Show’.” Pittsburgh Post-Gazette, December 25, 2004.

Street, 1615 L., NW, Suite 800 Washington, and DC 20036 202 419 4300 | Main 202 419 4349 | Fax 202 419 4372 | Media Inquiries. “Sharp Racial Divisions in Reactions to Brown, Garner Decisions.” Pew Research Center for the People and the Press, December 8, 2014.

Susman, Gary. “Rep: Chappelle’s Show’’ Delay Not due to Drugs.” Entertainment Weekly’s Accessed April 2, 2016.

“The Seattle Times: Television: Network Scrambling after Dave Chappelle’s Sudden Departure.” Accessed April 2, 2016.

Times, Los Angeles. “Read Chris Rock’s 2016 Oscars Opening Monologue.” Accessed April 3, 2016. “Chappelle DVD Sales Set Record.” Accessed April 2, 2016.

“Undercover Brother (2002) – Box Office Mojo.” Accessed April 1, 2016.

“Vox Magazine – Why Chappelle Is the Man.” Accessed April 2, 2016.

Wallace, Amy. “Dave Chappelle at the Comedy Cellar: The Funniest Night on Earth.” GQ, June 4, 2014.

“Why Dave Chappelle Went Crazy?” Accessed March 29, 2016.

Will Gorham. Clean Mic. Documentary, 2008.

Wisniewski, K. A., ed. The Comedy of Dave Chappelle: Critical Essays, n.d.

Wolk, Josh. “EW Investigates the Disappearance of Dave Chappelle.” Entertainment Weekly’s Accessed March 29, 2016.

Zinoman, Jason. “Chappelle Returns to Hartford (All Is Forgiven).” The New York Times, August 24, 2014.

[1] “Chappelle’s Show – Season 2 Episode 4” (Comedy Central, n.d.).

[2] Kevin Powell and 2006, “Heaven Hell Dave Chappelle,” Esquire, April 30, 2006,

[3] “Chappelle’s Show – Season 2 Episode 4,” 4.

[4] Andrew Wallenstein Hollywood Reporter, “Money Talks in ‘Chappelle’s Show’ Universe,”, April 19, 2004.

[5] Andrew Wallenstein Hollywood Reporter, “Money Talks in ‘Chappelle’s Show’ Universe,”, April 19, 2004.

[6] Andrew Wallenstein Hollywood Reporter, “Dave Chappelle Inks $50 Million Deal,”, August 3, 2004.

[7] Josh Wolk, “EW Investigates the Disappearance of Dave Chappelle,” Entertainment Weekly’s

[8] Corey Moss, “Dave Chappelle Reportedly In Mental Health Facility,” MTV News.

[9] “Why Dave Chappelle Went Crazy?,”

[10] Inside Actors Studio with Dave Chappelle, Talk-Show, (2008).

[11] Gil Kaufman 5/16/2005, “Dave Chappelle Speaks: ‘I’m Not Crazy; I’m Not Smoking Crack’,” MTV News, accessed.

[12] Oprah, “Chappelle’s Story,”,

[13] Powell “Heaven Hell Dave Chappelle.”

[14] “Dave Chappelle Kills at First Radio City Gig,” Rolling Stone, June 19, 2014.

[15] Ibid.

[16] Oprah, Dave Chappelle on Oprah – Why He Left,

[17] Will Gorham, Clean Mic, Documentary, (2008).

[18] Inside Actors Studio with Dave Chappelle.

[19] “On the Beach With Dave Chappelle,” Time, May 15, 2005.

[20] Jenny Hontz, “TV’s Race Card,” Variety, July 8, 1998,

[21] Paul Mooney and Dave Chappelle, Black Is the New White, n.d.

[22] Will Gorham, Clean Mic.

[23] Oprah, “Chappelle’s Story,”

[24] Hontz, “TV’s Race Card.”

[25] 1615 L. Street et al., “Sharp Racial Divisions in Reactions to Brown, Garner Decisions,” Pew Research Center for the People and the Press, December 8, 2014.

[26] Nick Kotz, “‘When Affirmative Action Was White’: Uncivil Rights,” The New York Times, August 28, 2005.

[27] George Lipsitz, The Possessive Investment in Whiteness (Temple University Press, 1998).

[28] Alana Semuels, “White Flight Never Ended,” The Atlantic, July 30, 2015,

[29] Nikole Hannah-Jones, “Segregation Now …,” The Atlantic, May 2014.

[30] “Mrs. Clinton Campaign Speech – Super-Predators,”, accessed March 27, 2016,

[31] Inside Actors Studio with Dave Chappelle.

[32] Ibid.

[33] Ibid.

[34] Ibid.

[35] Ibid.

[36] Ibid.

[37] Scott Saul, Becoming Richard Pryor, Reprint edition (S.l.: Harper Perennial, 2015).

[38] Mooney and Chappelle, Black Is the New White.

[39] Azure Gilman, “Explaining the Black-White Wage Gap,” Freakonomics, October 6, 2011,

[40] Just For Laughs, Dave Chappelle Stand Up – 1993, accessed April 4, 2016,

[41] “Dave Chappelle (Ft. James Lipton & Students of Pace School of Design) – Inside The Actor’s Studio Interview,” Genius, accessed March 30, 2016,

[42] Inside Actors Studio with Dave Chappelle.

[43] “Dave Chappelle (Ft. James Lipton & Students of Pace School of Design) – Inside The Actor’s Studio Interview.”

[44] Ibid.

[45] Ibid.

[46] Tamra Davis, Half Baked, Comedy, Crime, (1998).

[47] Inside Actors Studio with Dave Chappelle.

[48] Ibid.

[49] Dave Chappelle – Killing Them Softly.

[50] Dave Chappelle: Killin’ Them Softly,

[51] “Dave Chappelle Kills at First Radio City Gig.”

[52] Amy Wallace, “Dave Chappelle at the Comedy Cellar: The Funniest Night on Earth,” GQ, June 4, 2014,

[53] Ibid.

[54] Inside Actors Studio with Dave Chappelle.

[55] Mooney and Chappelle, Black Is the New White.

[56] “Undercover Brother (2002) – Box Office Mojo”,

[57] Oprah, “Chappelle’s Story.”

[58] Inside Actors Studio with Dave Chappelle.

[59] “Chappelle’s Show – Season 3 Episode 2,” Chappelle’s Show (Comedy Central, July 16, 2006), 3.

[60] Oprah, “Chappelle’s Story.”

[61] Chappelle’s Show,

[62] “Chappelle’s Show – Season 1 Episode 4,” Black Reparations (Comedy Central, February 12, 2003).

[63] “Vox Magazine – Why Chappelle Is the Man,” accessed April 2, 2016,

[64] Andrew Wallenstein Hollywood Reporter, “Money Talks in ‘Chappelle’s Show’ Universe.”

[65] “Vox Magazine – Why Chappelle Is the Man.”

[66], “Chappelle DVD Sales Set Record,”,

[67] Andrew Wallenstein Hollywood Reporter, “Money Talks in ‘Chappelle’s Show’ Universe.”

[68] Jennifer Vineyard 2/3/2006, “Dave Chappelle Comes Clean On ‘Oprah,’” MTV News,

[69] Oprah, Dave Chappelle on Oprah – Why He Left,

[70] “Chappelle’s Show – Season 2 Episode 11,” Chappelle’s Show (Comedy Central, March 31, 2004).

[71] Oprah, Dave Chappelle on Oprah.

[72] Andrew Wallenstein Hollywood Reporter, “Money Talks in ‘Chappelle’s Show’ Universe.”

[73] “The Seattle Times: Television: Network Scrambling after Dave Chappelle’s Sudden Departure,” accessed April 2, 2016,

[74] Andrew Wallenstein Hollywood Reporter, “Money Talks in ‘Chappelle’s Show’ Universe.”

[75] Ibid.

[76] Mooney and Chappelle, Black Is the New White.

[77] “Star’s Illness Delays ‘Chappelle’s Show’,” Pittsburgh Post-Gazette, December 25, 2004.

[78] Gary Susman, “Rep: Chappelle’s Show’’ Delay Not due to Drugs,” Entertainment Weekly’s, accessed April 2, 2016,

[79] Oprah, Dave Chappelle on Oprah.

[80] Oprah, “Chappelle’s Story.”

[81] Ibid.

[82] Oprah, Dave Chappelle on Oprah.

[83] Inside Actors Studio with Dave Chappelle.

[84] Oprah, “Chappelle’s Story,”,

[85] Moss, “Dave Chappelle Reportedly In Mental Health Facility.”

[86] Inside Actors Studio with Dave Chappelle.

[87] “An Open Letter From Dave Chappelle to His White Fans,” PopMatters

[88] Oprah, Dave Chappelle on Oprah – Why He Left, accessed January 22, 2016,.

[89] Ibid.

[90] “Chappelle’s Show: The Lost Episodes,”, 4, 2016,.

[91] Oprah, “Chappelle’s Story.”

[92] Oprah, Dave Chappelle on Oprah.

[93] Ibid.

[94] “An Open Letter From Dave Chappelle to His White Fans.”

[95] Ibid.

[96] Ibid.

[97] Ibid.

[98] K. A. Wisniewski, ed., The Comedy of Dave Chappelle: Critical Essays, n.d.

[99] Powell and 2006, “Heaven Hell Dave Chappelle.”

[100] “Dave Chappelle Performs to Benefit Cringe Humor Show Creator Masavia…,”

[101] “Punch Line Comedy Club – San Francisco, CA ::,”

[102] “Oddball Comedy & Curiosity Festival,” Funny Or Die,

[103] “Dave Chappelle Returns To Hartford, Performs Before Supportive Crowd,” Tribunedigital-Thecourant.

[104] Aisha Harris and Matthew Dessem, “Dave Chappelle Turns Hartford Incident With ‘Room Full of White People’ Into Comedy,” Slate, September 5, 2013.

[105] Ibid.

[106] “Dave Chappelle Walks Off Stage in Hartford,” NBC Connecticut, accessed March 30, 2016,–221744821.html.

[107] Bradford Evans August 30 and 2013, “Dave Chappelle Was Heckled and Walked Offstage Last Night in Hartford, CT,” Splitsider, August 30, 2013,

[108] Jason Zinoman, “Chappelle Returns to Hartford (All Is Forgiven),” The New York Times, August 24, 2014,

[109] “Dave Chappelle Returns To Hartford, Performs Before Supportive Crowd.”

[110] Michel Gondry, Dave Cappelle’s Block Party (Rogue Pictures, 2006).

[111] Chris Rock Verified account,

[112] Los Angeles Times, “Read Chris Rock’s 2016 Oscars Opening Monologue,”, accessed April 3, 2016,

[113] Inside Actors Studio with Dave Chappelle.

[114] Aisha Harris and Matthew Dessem, “How Much Do Chappelle’s Show and Key & Peele Have in Common, Really?,” Slate, February 18, 2015.