Dave Chappelle

A riotous, racially charged comedian whose career was on fire until he very publicly burned out in 2005, Chappelle began doing stand-up at age 14. After making his film debut at 20 with a silly supporting role in Mel Brooks' Robin Hood: Men in Tights, Chappelle spent the next decade toiling in similarly thankless, toothless parts (Tom Hanks' best friend in You've Got Mail, the short-lived sitcom Buddies) that failed to capitalize on his talents. The cult stoner flick Half Baked, which he also wrote, and a few stand-up specials were the only projects that gave an indication of his success to come. In 2003, Chappelle's Show — a hybrid of stand-up, surreal sketches and music (Mos Def, Snoop Dogg, etc.) — premiered on Comedy Central, and overnight he became a household name. Whether portraying the famous (a basketball-playing Prince, a "bitch"-screaming Rick James), or the fictional (a crackhead competing on Survivor, a blind black man who happens to be a member of the Ku Klux Klan), Chappelle was consistently hilarious, and the show was popular both when it aired and in its subsequent DVD release. In early 2005, the sudden star signed a reported $50 million deal with Comedy Central's parent company, Viacom, for two more years. But in May, in the midst of filming Season 3, Chappelle up and disappeared, which prompted rumors of drug abuse and mental instability. He soon resurfaced — in South Africa — where the Muslim performer said he went for a "spiritual retreat." In 2006 he explained his erratic actions on the talk-show circuit, telling Oprah Winfrey and Inside the Actors Studio's James Lipton that he bailed because he felt like "a prostitute" and had begun questioning whether he was "dancing or shuffling," meaning he wondered whether white folks were laughing with him or at him. Although in the summer of 2006 Comedy Central did air segments from the aborted third season, Chappelle never went back to his eponymous series. Instead he returned to his stand-up roots, appearing in the critically acclaimed film Block Party and living a comparatively quiet life in Ohio with his family.