Well, hearing that he’s kind of “winging it” and he won’t do his monologue in rehearsal partially explains why it’s “a little terrifying.” However, it also speaks to the trust Lorne Michaels has in Chappelle to deliver when he walks through that door to kick off the show.

The comedian recently sat down for a rare interview in which he recalled giving the MAGA leader "a chance" during his 2016 postelection monologue.