Dave Chappelle

Dave Chappelle hasn’t been a regular guest on The Howard Stern Show, but whenever he's mentioned or referenced, it’s often in admiration of his comedic genius and unique approach to tackling social and cultural topics. Over the years, Howard Stern has occasionally discussed Chappelle's career, including his work on Chappelle’s Show and his bold decisions, like stepping away from fame at the height of his success.

If Chappelle has made specific appearances, they might have included discussions about his rise in comedy, his experiences in Hollywood, or his philosophical take on fame and society. These themes align well with Stern’s interview style, where he often delves deep into the personal lives and motivations of his guests.