James Lipton, who died on Monday at the age of 93, made his name conducting in-depth interviews of actors, comedians, filmmakers and others on the long-running series “Inside the Actors Studio” when it was on Bravo TV. Though Lipton could come off as self-important or sycophantic, and was parodied more than once, there’s a reason the show was a hit. He got good stuff.

Here’s a look at some of his more memorable encounters:

Dave Chappelle

After abruptly leaving his Comedy Central series “Chappelle’s Show” and traveling to Africa in 2005, Dave Chappelle sat down with Lipton for a wide-ranging conversation to discuss, among other things, his thought process leading up to the walkout. “I had to make choices,” he told Lipton, adding later, “I like entertaining. And the higher up I go, for some reason, the less happy I am.” Below, you can see clips from the interview, and watch it in full here.