John Mulaney, the guest on this milestone 500th episode of The Hollywood Reporter’s Awards Chatter podcast, is one of the most popular and respected comedians of his generation. He’s a 40-year-old comedian, writer, producer and actor who already has to his name a Peabody Award and 18 Emmy nominations, two of which resulted in wins.

Mulaney, who was born and raised in Chicago, landed a writing job at Saturday Night Live at just 25. There, he co-created, with Bill Hader, one of the show’s most beloved characters, Stefon; and he has often since returned to the show to host the show, becoming a member of its “Five-Timers Club” whose almost annual appearances, to quote The New York Times, “have become one of the show’s more enjoyable traditions in this current era of its history.”

But Mulaney is best known for his standup, including five televised specials, the most recent being John Mulaney: Baby J — a candid exploration of what led up to and resulted from his recent stint in rehab — which dropped on Netflix back in April and has brought him some of the best notices of his career.

Over the course of this episode, Mulaney reflects on his early interest in comedy and study of its practitioners past and present; his experience as a writer who moved in front of the camera on SNL; what happened with his short-lived multi-camera sitcom Mulaney, and why, shortly after its cancelation, he declined an invitation to host The Daily Show; the material at the center of his standup specials, including classics riffs like Donald Trump’s presidency being the equivalent “a horse set loose in a hospital” and “All the kids like Bo Burnham more because he’s currently less problematic! Likability is a jail!”; whether or not standup comedy, in general, is moving more in the direction of dark, personal, confessional stuff, in the wake of Hannah Gadbsy’s Nanette, Jerrod Carmichael’s Rothaniel and now Mulaney’s Baby J; if he’d be up for hosting the Oscars; plus much more.