DAVE CHAPPELLE

Dave Chappelle possesses one of the most unique skill sets in this bunch. He is not only a successful actor, but he’s also a well-respected standup comedian that brought home numerous awards and accolades throughout his career, including a pair of Emmy Awards and three Grammys. Chappelle started his career in high school, when he performed comedy shows in nightclubs. In an interview later, Chappelle mentioned that his comedy performance was greatly influenced by Eddie Murphy, Richard Pryor, Chris Rock, etc.

During the 90s, Chappelle appeared in a couple of successful movies, including Mel Brooks’s 1993 film Robin Hood: Men in Tights and The Nutty Professor alongside Eddie Murphy. In 2016, he, his lawyers and manager received a hefty $20 million deal with Netflix for his comedy specials. Now that’s a deal that may be hard to beat. In 2020 Chappelle’s Netflix special won the Grammy Award for Best Comedy Album.