Dave Chappelle in Chappelle's Show (2003)

Dave Chappelle in The Age of Spin: Dave Chappelle Live at the Hollywood Palladium (2017)

Dave Chappelle and Charlie Murphy in True Hollywood Stories: Prince & Red Balls Energy Drink (2004)

Dave Chappelle and Charlie Murphy in Chappelle's Show (2003)

Wayne Brady and Dave Chappelle in Chappelle's Show (2003)

Dave Chappelle, Charlie Murphy, and Donnell Rawlings in Chappelle's Show (2003)

Dave Chappelle and John Mayer in Chappelle's Show (2003)

Dave Chappelle, Carolyn Ditmars, Christine Ditmars, and Cynthia Ditmars in Chappelle's Show (2003)

Neal Brennan and Dave Chappelle in Chappelle's Show (2003)

Dave Chappelle in Saturday Night Live (1975)

Dave Chappelle and Bradley Cooper in A Star Is Born (2018)

Jerry Seinfeld and Dave Chappelle in Comedians in Cars Getting Coffee (2012)

Dave Chappelle and Olivia Baseman in Chappelle's Show (2003)

Christina Ricci, Ben Affleck, Janeane Garofalo, Martha Plimpton, Casey Affleck, Courtney Love, Jay Mohr, Angela Featherstone, Dave Chappelle, and Paul Rudd in 200 Cigarettes (1999)

Danny DeVito, Norm MacDonald, and Dave Chappelle in Screwed (2000)

Martin Lawrence and Dave Chappelle in Blue Streak (1999)

Christina Ricci, Ben Affleck, Janeane Garofalo, Martha Plimpton, Courtney Love, Jay Mohr, Angela Featherstone, Kate Hudson, Dave Chappelle, and Paul Rudd in 200 Cigarettes (1999)

Christina Ricci, Ben Affleck, Janeane Garofalo, Casey Affleck, Courtney Love, Jay Mohr, Tori Spelling, Angela Featherstone, Kate Hudson, Dave Chappelle, and Paul Rudd in 200 Cigarettes (1999)

Dave Chappelle in Dave Chappelle: For What It's Worth (2004)