Pete Holmes hosted his own late-night talk show on TBS, The Pete Holmes Show, that aired after Conan in 2013-2014. He’s still the host of the very popular podcast You Made It Weird and he’s back in New York City this fall filming an HBO pilot directed by Judd Apatow called Crashing, which revisits Pete’s own experiences in NYC a decade earlier when he was a young comedian who needed places to crash after his divorce. Pete and I go back personally to those days and I get him to go back even deeper.

Twelve-year-old Pete would think that this Pete Holmes is living the dream, but what would 22-year-old Pete have to say about how his life has unfolded?! He tells me all about it preparing to relive his young adult self for television in this conversation recorded at the Olive Tree Cafe above the Comedy Cellar.

So let’s get to it!