Dave Chappelle is best known for his satirical comedy sketch series Chappelle’s Show (2003–2006), which he starred in until quitting in the middle of production during the third season. After a hiatus, Chappelle returned to performing stand-up comedy across the U.S. By 2006, Chappelle was called the “comic genius of America” by Esquire and, in 2013, “the best” by a Billboard writer. In 2017, Rolling Stone ranked him No. 9 in their “50 Best Stand Up Comics of All Time”.

Chappelle has appeared in several films, including Robin Hood: Men in Tights (1993), The Nutty Professor (1996), Con Air (1997), You’ve Got Mail (1998), Blue Streak (1999), Undercover Brother (2002), Dave Chappelle’s Block Party (2005), Chi-Raq (2015), and A Star Is Born (2018). His first lead role was in the 1998 comedy film Half Baked, which he co-wrote. Chappelle also starred in the ABC comedy series Buddies (1996). In 2016, he signed a $20-million-per-release comedy-special deal with Netflix and released six stand-up specials under the deal.

He has received numerous accolades, including six Emmy Awards and three Grammy Awards as well as the Mark Twain Prize for American Humor. Chappelle received his first Emmy in 2017 for his guest appearance on Saturday Night Live. In 2018, he received a Grammy Award for his Netflix-produced comedy album The Age of Spin & Deep in the Heart of Texas. Equanimity, another Netflix special featuring Chappelle, was nominated in 2018 for three Emmys and received the award for Outstanding Variety Special (Pre-Recorded). In 2019, Chappelle was selected to receive the Mark Twain Prize for American Humor, which is presented by the Kennedy Center as America’s highest comedy honor. In 2020, Sticks & Stones earned Chappelle his third consecutive Grammy Award for Best Comedy Album.