Comedian Dave Chappelle has been dipping in and out of the spotlight ever since his abrupt exit from Comedy Central’s Chappelle’s Show in 2005. He’s only done two late night appearances since then (in 2006 and 2008 on NBC’s Late Night with Conan O’Brien), but he’s set to return to the late night world tonight with an appearance on Letterman, his first time on late night TV in over six years. He’s also doing The Tonight Show on Friday, with both appearances being in promotion of his string of shows at Radio City Music Hall next week. These shows will be his first announced NYC performances in over a decade.
A regular fixture on late night TV throughout his career, Dave Chappelle appeared most frequently on Late Night with Conan O’Brien, displaying a fun and natural chemistry with O’Brien in the whopping 19 standup and/or panel spots he did on the show between 1996 and 2008. Check out a classic Chappelle appearance on Conan from 2001 below: