Dave Chappelle

1990–2002: Early career and breakthrough[edit]

Chappelle was featured in a montage of random people telling jokes in the first episode of ABC's America's Funniest People, airing on September 13, 1990. Following his high school graduation, Chappelle moved to New York City to pursue a career as a comedian. He performed at Harlem's Apollo Theater in front of the "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.^[12] He quickly made a name for himself on the New York comedy circuit, even performing in the city's parks. In addition to weekend stand-up gigs, he honed his craft at Monday night "open mic" performances at places like the Boston Comedy Club on West 3rd Street, as late as the summer 1994.^[19] In 1992, he won critical and popular acclaim for his television appearance in Russell Simmons' Def Comedy Jam on HBO. It was his appearance on this show that allowed his popularity to truly begin rising, eventually allowing him to become a regular guest on late-night television shows such as Politically Incorrect, Late Show with David Letterman, The Howard Stern Show, and Late Night with Conan O'Brien. Whoopi Goldberg nicknamed him "The Kid".^[3] 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 to competing comedian Lester Barrie; Chappelle later joked about 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.^[20][21] 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 O. J. Simpson's being accused of murder.^[22] Chappelle played another supporting role in an early Doug Liman film, Getting In, in 1994.^[23] At age 19, he was the opening act for R&B soul singer Aretha Franklin.^[24]


Chappelle attracted the attention of television network executives and developed numerous pilots but none were picked up for development into a series.^[12][25] 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.^[26] 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, 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 that 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.^[27] Chappelle resisted and subsequently accused the network of racism. Shortly afterward Chappelle's father died and, after returning to Ohio, he considered leaving the entertainment business.^[12][25]


He later appeared as a stand-up insult comic who targets patrons of a nightclub in the 1996 comedy The Nutty Professor starring Eddie Murphy, one of his major comedic influences.^[28] He had a minor role in 1997's Con Air.^[29] 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", an episode of The Larry Sanders Show's sixth season, in which he and the executives of the show's unnamed television network satirize the treatment that scriptwriters and show creators were subjected to, as well as the executives' knee-jerk tendencies toward racial stereotypes.^[30]


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 "stoner" film, a genre that includes the Cheech & Chong films as well as more recent fare like Judd Apatow's Pineapple Express.^[31][32] In December 1998, Chappelle appeared as Tom Hanks' character's friend and confidant in You've Got Mail.^[33] In 1999, he appeared in the Martin Lawrence film Blue Streak.^[34]


In 2000, Chappelle recorded his first hour-long HBO special, Dave Chappelle: Killin' Them Softly, in Washington, D.C. He also starred alongside Norm Macdonald in the 2000 comedy film Screwed.^[35] He followed this with an appearance as "Conspiracy Brother" in the 2002 racial satire Undercover Brother.^[36]