In 2003, Chappelle became more widely known for his sketch comedy television series, Chappelle's Show, also co-written with Brennan, which ran until his retirement from the show two years later. The show continues to run in late-night syndication and on television networks around the world.
September 2017, he was awarded an Emmy Award for his guest appearance on Saturday Night Live.
Chappelle lives with his family in Yellow Springs, Ohio, and performs touring stand-up comedy all across the country. In 2009, Comedy Central ranked him No. 43 in the "100 Greatest Stand-Ups of All Time".
Chappelle was born in Washington, D.C., the youngest of three children. His father, William David Chappelle III, worked as a statistician before becoming a professor at Antioch College in Yellow Springs, Ohio. His mother, Yvonne Chappelle (née Reed), is biracial, and was a professor at Howard University, Prince George's Community College, and the University of Maryland, and is also a Unitarian Universalist minister. Chappelle also has a stepmother and a stepbrother. His great-grandfather is Bishop William D. Chappelle, a former president of Allen University.
Chappelle grew up in Silver Spring, Maryland, and attended Woodlin Elementary School. His parents were politically active, and the family house was visited by notable individuals including Pete Seeger and Johnny Hartman. The latter predicted he would be a comedian and, around this time, Chappelle's comic inspiration came from Eddie Murphy and Richard Pryor. After his parents separated, Chappelle stayed in Washington with his mother while spending summers with his father in Ohio. In 1991, he graduated from Washington's Duke Ellington School of the Arts, where he studied theatre arts.
Chappelle moved to New York City to pursue a career as a comedian. He performed at Harlem's famed Apollo Theater in front of the infamous "Amateur Night" audience, but he was booed off stage. Chappelle described the experience as the moment that gave him the courage to continue his show business aspirations. He quickly made a name for himself on the New York comedy circuit, even performing in the city's parks. Whoopi Goldberg nicknamed him "The Kid". At 19, he made his film debut as "Ahchoo" in Mel Brooks' Robin Hood: Men in Tights. He also appeared on Star Search three times but lost over competing comedian Lester Barrie; Dave later joked about the irony of him subsequently becoming more successful than Barrie. The same year, Chappelle was offered the role of Benjamin Buford "Bubba" Blue in Forrest Gump. Concerned the character was demeaning and the movie would bomb, he turned down the part. He parodied the film in the 1997 short "Bowl of Pork," where a dim-witted black man is responsible for the Rodney King beating, the LA riots and OJ Simpson being accused of murder. Chappelle played another supporting role in an early Doug Liman film, Getting In in 1994. At age 19, he was the opening act for R&B soul singer Aretha Franklin.
He attracted the attention of TV network executives and developed numerous pilots, but none was picked up for development into a series. In 1995, he made a guest appearance on an episode of ABC's popular sitcom Home Improvement. The storyline had Chappelle and real-life friend and comedian Jim Breuer ask Tim Taylor for advice on their girlfriends. The characters' single outing in the episode proved so popular that ABC decided to give them their own spin-off sitcom titled Buddies. However, after taping a pilot episode, Jim Breuer was fired and replaced with actor Christopher Gartin. Buddies premiered in March 1996 to disappointing ratings, and the show was canceled after only five episodes out of 13 had been produced.
After the failure of Buddies, Chappelle starred in another pilot. According to Chappelle, the network was uncomfortable with the African-American cast and wanted white actors added. Chappelle resisted and subsequently accused the network of racism. Shortly afterwards, Chappelle's father died, and Chappelle, returning to Ohio, considered leaving the entertainment business.
He later appeared as a nightclub comedian in the 1996 comedy The Nutty Professor starring Eddie Murphy, one of his major comedic influences. The movie grossed nearly $129 million on a budget of $54 million. He had a minor role in 1997's Con Air which made $26 million after production costs. At the beginning of 1998, he did a stand-up performance for HBO Comedy Half-Hour. That same year, he appeared in "Pilots and Pens Lost," a 1998 episode of The Larry Sanders Show's sixth season, in which he and the executives of the show's unnamed television network satirized the treatment to which scriptwriters and show creators were subjected, as well as the executives' knee-jerk tendencies toward racial stereotypes.
He and Neal Brennan co-wrote the 1998 cult stoner film Half Baked, Chappelle's first starring role, about a group of marijuana-smoking friends trying to get their other friend out of jail. It made money at the box office and remains a classic so-called "stoner" film, a genre that includes the "Cheech and Chong" films as well as more recent fare like Judd Apatow's Pineapple Express. In December 1998, Chappelle appeared as Tom Hanks' character's friend and confidant in You've Got Mail. The $65 million movie made nearly $116 million at the box office. In 1999, he appeared in the Martin Lawrence film Blue Streak, which made $117 million at the box office.
In 2000, Chappelle recorded his first hour-long HBO special, Dave Chappelle: Killin' Them Softly, in Washington, DC. He followed this up with an appearance as "Conspiracy Brother" in the 2002 racial satire Undercover Brother.
In 2003, Chappelle debuted his own weekly sketch comedy show on Comedy Central called Chappelle's Show. The show parodied many aspects of American culture, including racial stereotypes, politics and pop culture. Along with comedy skits, the show also featured musical performances by mostly hip-hop and soul artists. He promoted the work of other black comedians as well, most notably Paul Mooney and Charlie Murphy.
Due to the show's popularity, Comedy Central's new parent company Viacom reportedly offered Chappelle a $55 million contract (giving Chappelle a share of DVD sales) to continue production of Chappelle's Show for two more years, while allowing him to do side projects. Chappelle has said that sketches are not his favorite form of comedy, and that the show's format was somewhat like short films.
In June 2004, based on the popularity of the "Rick James" sketch, it was announced that Chappelle was in talks to portray James in a biopic from Paramount Pictures, also owned by Viacom. James's estate disagreed with the proposed comical tone of the film and put a halt to the talks.
That same month, Chappelle recorded his second comedy special, this time airing on Showtime, Dave Chappelle: For What It's Worth, at San Francisco's Fillmore Auditorium, where his idols, including Lenny Bruce, George Carlin, Richard Pryor, and Robin Williams, had performed.
In a June 2004 stand-up performance in Sacramento, California, Chappelle walked off the stage after berating his audience for constantly shouting "I'm Rick James, bitch!" which had become a catchphrase from his popular "Rick James" sketch. After a few minutes, Chappelle returned and resumed by saying, "The show is ruining my life." He stated that he disliked working "20 hours a day" and that the popularity of the show was making it difficult for him to continue his stand-up career, which was "the most important thing" to him. He told the audience:
Season 3 was scheduled to begin airing on May 31, 2005, but earlier in May, Chappelle stunned fans and the entertainment industry when he abruptly left during production and took a trip to South Africa. Chappelle said that he was unhappy with the direction the show had taken, and expressed in an interview with Time his need for reflection in the face of tremendous stress:
Immediately following Chappelle's departure, tabloids quickly and repeatedly speculated that Chappelle's exit was driven by drug addiction or a mental health issue, rather than ethical or personal concerns as Chappelle claimed.
The break from Comedy Central also meant a rift with longtime collaborator Neal Brennan as well as walking away from a $50 million contract.
Chappelle was the star and a producer of the Michel Gondry-directed documentary Dave Chappelle's Block Party, which chronicles him hosting a free concert in the Clinton Hill neighborhood of Brooklyn on September 18, 2004. Several musical artists, including Kanye West, The Roots, Erykah Badu, Mos Def, Dead Prez and Jill Scott, are featured in the movie both performing in the concert and in conversation off-stage. He brought Yellow Springs residents to Brooklyn at his own expense. Another highlight of the event was the temporary reunion of 1990s hip-hop group The Fugees.
Chappelle toured several cities in February and March 2006 to promote the film under the name "Block Party All-Stars Featuring Dave Chappelle". Universal Pictures' genre division, Rogue Pictures, released the film in the U.S. on March 3, 2006. It was a success, grossing a total of $11.7 million on a $3 million budget.
In June 2005, Chappelle performed impromptu stand-up shows in Los Angeles. He then went on a tour that began in Newport, Kentucky, not far from his Ohio home. He made a surprise appearance on HBO's Def Poetry, where he performed two poems, titled "Fuck Ashton Kutcher" and "How I Got the Lead on Jeopardy!"
In an interview with Oprah Winfrey that aired on February 3, 2006, Chappelle explained his reasoning for quitting Chappelle's Show. He also expressed his contempt for the entertainment industry's tone-deafness toward black entertainers and audiences:
Chappelle was interviewed for Inside the Actors Studio on December 18, 2005, at Pace University's Michael Schimmel Center for the Arts. The show premiered on February 12, 2006. Four days earlier, he had introduced the musical tribute to Sly Stone at the 48th Annual Grammy Awards.
Chappelle said on Inside the Actors Studio that the death of his father seven years prior influenced his decision to go to South Africa. By throwing himself into his work, he had not taken a chance to mourn his father's death. He also said the rumors that he was in drug or psychiatric treatment only persuaded him to stay in South Africa. He said,
Chappelle said that he felt some of his sketches were "socially irresponsible". He singled out the "pixie sketch" in which pixies appear to people and encourage them to reinforce stereotypes of their races. In the sketch, Chappelle is wearing blackface and is dressed as a character in a minstrel show. According to Chappelle, during the filming of the sketch, a white crew member was laughing in a way that made him feel uncomfortable and made him question himself. Chappelle said, "It was the first time I felt that someone was not laughing with me but laughing at me."
During these interviews, Chappelle did not rule out returning to Chappelle's Show to "finish what we started," but promised that he would not return without changes to the production, such as a better working environment. He desired to donate half of the DVD sales to charity. Chappelle expressed disdain at the possibility of his material from the unfinished third season being aired, saying that to do so would be "a bully move," and that he would not return to the show if Comedy Central were to air the unfinished material. On July 9, 2006, Comedy Central aired the first episode of Chappelle's Show: The Lost Episodes. After the DVD release, Chappelle was interviewed by Anderson Cooper on CNN and reiterated he would not return to Chappelle's Show. An uncensored DVD release of the episodes was made available on July 25.
The show still plays in syndication on several television networks, despite the relatively small number of episodes compared to most American syndicated television programs.
Chappelle has been known to make impromptu and unannounced appearances at comedy venues, and continues to do so following his post–Chappelle's Show return to standup.
In April 2007, Chappelle set a stand-up endurance record at the Laugh Factory Sunset Strip comedy club, beating comedian Dane Cook's record of three hours and 50 minutes. In December of the same year, Chappelle broke his own record with a time of six hours and 12 minutes. Cook reclaimed the record in January 2008, with a time of seven hours. On November 19, 2009 Chappelle performed at the Laugh Factory again, where it was speculated that he would attempt to take back the record. However, he was disqualified according to the club owner after he left the stage five hours into his routine.
Chappelle again appeared on Inside the Actors Studio and, in celebration of the show's 200th episode, he humorously interviewed the show's usual host, James Lipton. The episode aired on November 11, 2008. He appeared again on Inside the Actors Studio in 2013, for its 250th episode.
In August 2011, Chappelle appeared at Comedy Jam in San Francisco.
In August 2013, Chappelle returned to full-time touring stand-up, serving as a headliner when he was featured during the Oddball Comedy & Curiosity festival. Sponsored by Funny or Die, Chappelle co-headlined with comedy act Flight of the Conchords.
During a stop in Hartford, Chappelle walked off the stage due to heckling from the crowd that lasted throughout his entire performance. The heckling was so raucous that it drowned out Chappelle's voice over the PA system and included chants of "White Power", a line used in a Chappelle's Show episode that was viewed as wildly inappropriate and out-of-context by other audience members who later wrote about the event. A few days later, to follow up on the Hartford incident, Chappelle stopped in Chicago for a performance where comedy website ComedyHype.Com acquired and released audio of him being heard on stage responding to the heckling in Hartford. Chappelle referenced the Hartford incident, stating that "young, white, alcoholic[s]" should be blamed for the prior incident, that he hoped North Korea would bomb Hartford, that in the future he would not stop in Hartford for gas, and finally summarizing his feelings on the situation by saying, "Fuck Hartford!" However, in August 2014 Chappelle returned to Hartford for a surprise appearance at the 2014 Oddball Festival and received multiple standing ovations during his set.
In June 2014, Chappelle made his first major New York City appearance in eleven years, performing ten nights at Radio City Music Hall. Chappelle promoted the dates by appearing on The Today Show, The Tonight Show and Late Night with David Letterman.
In 2015, Chappelle appeared in the Spike Lee film, Chi-Raq, his first film role in 13 years.
On November 12, 2016, Chappelle made his hosting debut on Saturday Night Live, with A Tribe Called Quest as musical guest.
On November 21, 2016, Netflix revealed that they will be releasing three new stand-up comedy specials from Chappelle in 2017. Chappelle was paid $60 million as part of the deal, $20 million per special.
On March 21, 2017, Netflix released two never-before-seen specials which hail directly from Chappelle's personal comedy vault. These specials were filmed at Austin City Limits Live in April 2015 and at the Hollywood Palladium in March 2016. The specials marked the comedian's first concert specials in 12 years. The specials proved to be an immediate success, as Netflix announced a month later that they were the most viewed comedy specials in Netflix's history.
Chappelle has been involved in a number of charitable events. In 2004, he donated his time to Seeds of Peace International Camp, a camp located in Otisfield, Maine, which brings together young leaders from communities in conflict.
Chappelle has been praised by fellow comedians for his work. Katt Williams believes Chappelle to be the greatest stand-up comedian alive, while Kevin Hart also considers Chappelle to be the greatest stand-up comedian of all time.
In 2009, his show was the subject of a book of critical essays, The Comedy of Dave Chappelle, edited by University of Maryland doctoral student K. A. Wisniewski. His work, as well as that of Margaret Cho, was also the subject of a book by a Canadian dramaturg Elizabeth Ludwig, American Stand-Up and Sketch Comedy, that was published at the end of 2010. A monograph published by the University of Gothenburg titled Representations of ethnicity in stand-up comedy: A study of the comedy of Dave Chappelle examined the racial significance of language used in Chappelle's routines.
Chappelle's abrupt departure from his show in 2005 continues to be a focus of interviews and profiles of Chappelle and of Chappelle's own comedy.
In April 2013, Charlie Sheen appeared on Conan O'Brien's talk show and claimed that in 2011 he had laughed so hard while watching a Chappelle's Show episode that he experienced a ruptured hernia, and was rushed to a hospital.
In August 2013, Chappelle's impersonation of Prince from Chappelle's Show was selected by the singer as the cover art for his single "Breakfast Can Wait".
In his interview with Inside the Actors Studio host James Lipton, he said that his biggest influences in comedy are Richard Pryor, Eddie Murphy, Chris Rock, Paul Mooney, and Mel Blanc.
When asked about his earliest influence on comedy, Chappelle said, "You know who was a big influence on me that is really weird is Bugs Bunny, That's just weird. If you watch a lot of the stuff I do, you can almost see the influence in it, Because these animators would animate these performances that were off the hook, And the guy that, the guy that did the voices was Mel Blanc. This guy was like some kind of savant or genius or something, But they had some kind of real big comedic influence on me, like I liked those cartoons, I think that was my first real big comedy influence, was a rabbit."
When asked about the biggest influence on him in comedy, Chappelle spoke highly praise to Richard Pryor, "What a precedent he set. Not just as a comic, but as a dude. The fact that someone was able to open themselves wide-open like that. It's so hard to talk in front of people or to open yourself up to your closest friends. But to open yourself up for everybody: I freebase, I beat my women, I shot my car. And nobody's mad at Richard for that. They understand. Somehow they just understand. And when I was going through this thing this year, that is the example I would think to myself that gave me the courage to just go back on the stage."
Chappelle lives with his wife, Elaine Mendoza Erfe, sons Suleyman and Ibrahim, and daughter Sanaa on a 65-acre (260,000 m2) farm near Yellow Springs, Ohio. He also owned several houses in Xenia, Ohio. Chappelle told Yellow Springs' residents in September 2006, "Turns out you don't need $50 million to live around these parts, just a nice smile and a kind way about you. You guys are the best neighbors ever. That's why I came back and that's why I'm staying."
Chappelle converted to Islam in 1998. He told Time in May 2005, "I don't normally talk about my religion publicly because I don't want people to associate me and my flaws with this beautiful thing. And I believe it is beautiful if you learn it the right way."