1993 | 'Robin Hood: Men in Tights'

Chappelle landed his first major role in Mel Brooks' 1993 Robin Hood spoof, playing Ahchoo, one of Robin's men in tights, when he was only 19. The movie was met with mixed reviews but has since developed a cult following. At the end of the film, Robin (Cary Elwes) appoints Achchoo the new Sheriff of Rottingham. "A black sheriff?" the disbelieving crowd asks. "And why not?" Chappelle's character responds. "It worked in 'Blazing Saddles.' "
20th Century Fox
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