Dave Chappelle

Without a doubt one of the most gifted comics of his generation, Dave Chappelle emerged from the stand-up comedy circuit to become a noted performer on several HBO specials and as a guest star on sitcoms like "Home Improvement" (ABC, 1991-99). Following small but memorable roles in movies like "Robin Hood: Men in Tights" (1993), "The Nutty Professor" (1996) and "Con Air" (1997), Chappelle earned both acclaim and a huge following from his groundbreaking program, "Chappelle's Show" (Comedy Central, 2003-06). Chappelle's sketch series became a cultural phenomenon during its short run, thanks to unforgettable and hilarious sketches like Black Bush, a blind white supremacist who was actually black, and his parody of both Lil' Jon and pop icon Rick James, whose catchphrase, "I'm Rick James, Bitch!" entered the cultural zeitgeist. Despite the show's enormous popularity, Chappelle cracked under the pressure of stressful conditions and loss of creative control, leading to his abrupt departure at the start of the third season. After a brief departure from the public spotlight, he returned to his first love, stand-up, where Chappelle continued to prove his dominance while still maintaining his large and loyal fan base.

Born on Aug. 23, 1972 in Washington, D.C., Chappelle was raised in Silver Spring, MD by his father, William, later a professor at Antioch College, and his mother, Yvonne, a Unitarian minister and college professor at Howard University, who also spent time teaching in the Congo. His parents split when he was two years old. Later, he attended Woodlin Elementary School, where he performed poorly despite his academic home life, and later Arthur E. Morgan Middle School. Back in D.C., Chappelle went to high school at the Duke Ellington School of the Arts after spending half a school year at a public school, where the crack epidemic first exploded and began taking a huge toll on the city. His mother, who raised Chappelle and his two siblings, gave her son a copy of Time magazine with Bill Cosby on the cover, which first sparked his idea of becoming a comedian. Soon he began checking out the local comedy scene and during an open mic night, made his debut on stage at 14 years old with his mother, grandmother and brother in the audience.

Within a year of making his debut, Chappelle landed his big chance at stardom with a slot on amateur night at the famed Apollo Theater in Harlem, only to be booed offstage by the crowd. But the young comedian took the booing in stride - he later said that it was the best thing that happened to him - and began making strides in the tough-to-crack New York comedy circuit. His stand-up career took off like a shot, as he became one of the talked-about comedians working the clubs at the time. In 1992, he made appearances on "Russell Simmons' Def Comedy Jam" (HBO, 1991-2008) and "Six Comics in Search of a Generation" (Lifetime, 1992), and followed with his feature film debut as Ahchoo in Mel Brooks' "Robin Hood: Men in Tights" (1993). He gained further national exposure when he became the youngest comic to appear on the HBO special, "Comic Relief VI" (1994). The following year, Chappelle had a guest appearance on the hit sitcom, "Home Improvement" (ABC, 1991-99), which led to a pilot for a proposed spin-off sitcom called "Buddies," a Disney-produced show that premiered in 1996 and teamed him with the very unfunny Christopher Gartin. Despite the quick cancellation of the series - it only lasted four episodes - Disney was impressed enough with the ascendant star to offer him a $1 million development deal.

Chappelle clinched his big screen viability with a memorable turn as an insult comic who viciously degrades the weight problem of Professor Sherman Klump (Eddie Murphy) while he is on a date in "The Nutty Professor" (1996). He went on to a featured role as a wisecracking convict in the successful action thriller, "Con Air" (1997), and co-starred opposite Tommy Davidson and Jada Pinkett Smith in the box office flop, "Woo" (1998). In an attempt to pay homage to Cheech and Chong, Chappelle wrote and starred in the stoner comedy "Half Baked" (1998), in which he played several characters onscreen, including the aptly named Sir Smoka Lot. Chappelle next lent his distinctive, affable charm to supporting roles in a wide range of film projects, including "You've Got Mail" (1998), "200 Cigarettes" (1999) and "Blue Streak" (1999) before reviving his pot-head persona for the dismal revenge comedy "Screwed" (2000), opposite off-screen friend Norm MacDonald. In the Eddie Griffin blaxploitation comedy "Undercover Brother" (2002), Chappelle showed his edgier side as the paranoid, white-suspicious Conspiracy Brother, a taste of the more sharply pointed, politically incorrect comedy that characterized his stand-up and later his popular Comedy Central show.

After a stint as one of the many caller voices on Comedy Central's puppet prank call show "Crank Yankers" (2002-07), Chappelle inked a pact with the cable network to write, produce, host and star in his own half-hour sketch comedy series, "Chappelle's Show" (2003-06). The comic made the most of the creative freedom the series allowed, and quickly delivered a show that reflected his sensibilities: hip, edgy and frequently racially, sexually and Scatologically charged. Outrageous, but rarely offensive due to its intelligence, sharp observations and riotous humor, "Chappelle's Show" quickly garnered a loyal viewership addicted to over-the-top recurring characters like crackhead Tyrone Biggums and Negrodamus; scathing parodies of Rick James, Prince, rapper Lil' Jon and "The Real World;" and wild catch phrases ("I'm rich, beeyotch!") - all of which culminated with several Emmy nominations. In 2004, Comedy Central signed Chappelle to a $50 million contract for two more seasons, and the comedian was also poised to return to feature films with projects tailored especially to his newly appreciated talents as this millennium's new Eddie Murphy.

However, things quickly spiraled wildly and unpredictably out of control in the spring of 2005 when, after Chappelle reportedly taped nearly five episodes into his series' third season after a several-month delay due to an undisclosed illness, he became a no-show on the set for several days, prompting Comedy Central to halt production and announce that the comedy would not meet its anticipated May 31 launch. Days after the announcement, it was reported by Entertainment Weekly that Chappelle had flown from Newark, NJ to Capetown, South Africa on April 28 and voluntarily checked himself into an unnamed psychiatric facility for treatment. Various theories were floated for the comic's apparent meltdown, including creative differences with the cable network over his series' envelope-pushing content, an inability to cope with his overwhelming success, and an increased use of recreational drugs - long a staple of his onscreen persona. However, Chappelle insisted that he had merely embarked an a "spiritual retreat" in the wake of continuing creative frustrations and stress resulting from his Hollywood success, denying any drug use and saying that he had only had a 40-minute session with a psychiatrist while staying with friends in Durban. In 2006, Chappelle told Oprah Winfrey on her program that he would consider returning to his show if Comedy Central met certain conditions. "I felt in a lot of instances I was deliberately being put through stress," Chappelle said.