Dave Chappelle Season 12, Episode 1206 Original Airdate: February 12, 2006 Dave Chappelle first debuted his comedic talents at the age of fourteen while studying acting and literary media at the Duke Ellington School of the Arts. Within a year he was invited on stage at the famed Apollo Theater in Harlem, New York. He made a name for himself along East Coast clubs before breaking into TV on Russell Simmons' “Def Comedy Jam” on HBO and receiving the honor of being the youngest featured comic to perform on “Comic Relief VI” at age twenty. Chappelle then moved into film, appearing in “Robin Hood: Men in Tights,” “You've Got Mail,” “Half Baked,” and “Con Air.” Chapelle's fame skyrocketed with the success of the Comedy Central hit “Chappelle's Show.” The show's smart and controversial social and political commentary made it an instant sensation and gave Chappelle status as one of comedy's reigning stars.