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He starred in and co-created the satirical comedy sketch series Chappelle's Show β before quitting in the middle of production during the third season. After a hiatus, Chappelle returned to performing stand-up comedy across the U. His first lead role was in the comedy film Half Baked , which he co-wrote. Chappelle also starred in the ABC comedy series Buddies Kennedy Center for the Performing Arts as America's highest comedy honor. After his parents separated, Chappelle stayed in Washington with his mother while spending summers with his father in Ohio.
In high school he worked as an usher in Ford's Theatre. 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, 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.
In addition to weekend stand-up gigs, he honed his craft at Monday night "open mic" performances at places such as the Boston Comedy Club on West 3rd Street, as late as the summer 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". He also appeared on Star Search three times but lost to competing comedian Lester Barrie ; Chappelle later joked about becoming more successful than Barrie.