David Chappelle was enraptured by stand-up comedy since his days as an elementary school student at Woodlin Elementary School in Silver Spring, Maryland, and a middle school student in Yellow Springs, Ohio, where his father William was a professor of voice and music at Antioch College. At 14, Chappelle gathered the courage to perform on stage at the famed Apollo theater in harlem, New York. After his parents' divorce, Chappelle moved to Washington, D.C., with his mother, Yvonne Seon (a Unitarian Universalist minister). He spent summers with his father in Yellow Springs and attended and graduated from Duke Ellington School of the Arts (a renowned performing arts high school in Washington, DC), where he majored in literary and theatre arts.
In 1992 Dave Chappelle made his first TV appearance on Def Comedy Jam. Then the next year Dave made his first appearance as an actor in Robin Hood: Men in Tights as Ahchoo, and then in Undercover Blues as Ozzie. The period from 1994 to 1997 for Dave was a repetitive cycle of TV appearances, fairly minor stand-up shows, and rather low-budget films. One of the most notable things Dave did during this time was that he was given his first shot at his own show, The Dave Chappelle Project, but the show was short-lived. In 1998, however, Dave became a hit cult movie star in Half Baked, a film Dave co-wrote (with Neal Brennan) and produced (uncredited), which follows the lives of four stoners. After Half Baked, Dave did more TV appearances, stand-up shows, and films. In 2000, Dave made a rather large hit appearance on his HBO one-night stand-up show, Dave Chappelle: Killin' 'Em Softly.
In 2003, Chappelle debuted his own weekly television show on Comedy Central, Chappelle's Show. His sketch comedy heavily skewers racial stereotypes and slurs, including Chappelle's African-American heritage. This, combined with pointed social and political commentary, quickly gained the show great popularity. By the end of the second season, it was one of the highest-rated shows on basic cable, and second only to South Park on Comedy Central. Additionally, the DVD set of the first season became the best-selling DVD of a television show to date. Due to the show's popularity, Comedy Central's parent company Viacom reportedly offered Chappelle a $50 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.
One of Chappelle's most widely-known bits has Chappelle portraying late funk musician Rick James during his drug-abusing years in the Rick James sketch. "I'm Rick James, B----!"—which James himself acknowledged was a direct quote—has become a part of popular culture, as have many other Chappelle characters and sketches. However, Chappelle eventually grew weary of the phrase's popularity and told audience members who yelled it to "shut up." At an appearance at Southern Illinois University Carbondale, Chappelle stopped the show to deal with an audience member who would not stop repeating the phrase.
Dave Chappelle has also done two parodies of music videos, "P--- On You" and its remix, which parodies R&B singer R. Kelly's "Feeling on your Booty", and Ignition Remix.
The comedian stunned fans and the entertainment industry when he abruptly left during production of the third season of Chappelle's Show. He spent two weeks in South Africa before returning home to his 65-acre farm near Yellow Springs, and then returned to standup comedy. His decision triggered reports that he had mental or drug problems, which he denied. On May 11, 2005, news sources (most notably Entertainment Weekly) reported that Chappelle had checked himself into a psychiatric facility in South Africa. Chappelle denies this. On May 14, 2005, Time Magazine announced that one of their reporters had interviewed Chappelle in South Africa, and the comedian said no psychiatric treatments were occurring or necessary. Chappelle reportedly went to South Africa to purify himself and to do some soul searching. Chappelle has also said he was unhappy with the direction of his show. He has recently claimed that he felt pressured by network executives regarding the show's content.
Dave Chappelle's Show is on hiatus as of December 2005 while he sorts out unspecified personal issues. On August 3rd, co-star Charlie Murphy gave an interview to TV Guide stating that he believes that Dave Chappelle is finished with Chappelle's Show and would not be returning. Although Chappelle may be done with filming the show, Comedy Central has recently reported that they will release the un-aired sketches of the third season of "Chappelle's Show" into a couple of half hour episodes in mid-2006. A season three trailer was shown on Comedy Central during their Last Laugh '05 and then on their website.
Chappelle, himself, however, has expressed disdain at the possibility of his material from the unfinished third season being aired, saying not only does he feel that it is "a bully move," but that he would not return to the show if Comedy Central airs the unfinished material.
In late 2005, David Chappelle was reported to be back in the United States, at his house in Yellow Springs, Ohio and performed impromptu shows in Los Angeles and Newport, Kentucky.
David 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.
He was interviewed by Oprah Winfrey on her show on February 3, 2006 in the first televised interview with David Chappelle since he left Chappelle's Show. He stated in the interview that he "wasn't crazy" but the environment was "incredibly stressful." He continued:
"I would go to work on the show and I felt awful every day, that's not the way it was. ... I felt like some kind of prostitute or something. If I feel so bad, why keep on showing up to this place? I'm going to Africa. The hardest thing to do is to be true to yourself, especially when everybody is watching."
He did not rule out returning to Chappelle's Show to "finish what we started", but only under certain circumstances such as a better working environment. He also stated he would like to donate half of the DVD sales to charity, and to people that supported him. During an interview Chappelle said how the death of his father had an impact in his decision to go to the South Africa to get away from the stress of stardom. Chappelle looked up to his father for advice during his life and said in an interview at Inside the Actors Studio that he never had the chance to mourn his father's death. He also said the rumors that he was in drug treatment only persuaded him to stay in South Africa.
Dave Chappelle wrote and is featured in a Michel Gondry-directed film titled Dave Chappelle's Block Party that chronicles a Chappelle-hosted event, from the summer of 2004, in the Bedford-Stuyvesant neighborhood of Brooklyn, New York City. The highlight of the event was the reunion of popular '90s rap group The Fugees. Chappelle will be touring several cities in February and March 2006 to promote the film under the moniker "Block Party All-Stars featuring Dave Chappelle." The movie was released on March 3, 2006.