Born in Washington, D.C., the funny man known as Dave Chappelle got his start in the industry as a standup comedian before transitioning into screenwriting, television and film producing and acting. He’s appeared in movies like Undercover Blues, Con Air, Blue Streak and Half Baked, which was his first leading role. But it was hit sketch comedy series, Chappelle’s Show, that catapulted him into superstardom and set the stage for the revered comedian to air his thoughts on race, pop culture and politics. Despite his abrupt departure from the show during the taping of its third season (a move that topped headlines, generated controversy and caused allegations of insanity and drug use), Chappelle is still regarded as one of the best comedians to ever walk on stage. Comedy Central named him one of their “100 Greatest Stand-Ups of All Time” and moments from his hit show are now considered a part of American pop culture history.