20) Dave Chappelle

Chappelle changed comedy with Chappelle's Show, but at his best, he took an eight-year hiatus to commit to his role as a father. Years passed, and he is back to stand-up, now with a deal with Netflix, though he picks his projects very carefully. The irony makes his alienation from Hollywood a very poignant one.
Despite regular spots of controversy, Chappelle's impact on comedy remains huge and his intermittent returns drive home the message that he only does things on his terms. His early show is a cultural landmark in comedy history.
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Edited by Priscillah Mueni