10 Must-Hear Episodes of Pete Holmes’ Podcast, ‘You Made It Weird’

Pete Holmes is the host of You Made It Weird, a uniquely revealing interview podcast on which he encourages his guests — stand-up comics, clergy members, musicians, you name it — to get very, very weird about relationships, religion, and just about anything else they’d feel uncomfortable discussing with their parents. He’s recorded more than 350 shows — we asked him to pick his 5 favorite, then added 5 more of our own.

Pete’s top five:

Moshe Kasher Returns (Episode 197, 2014)

Kasher’s Racist Stephen Hawking character is a thing of beauty. In an extended tangent during a story about how the stand-up and memoirist blew the $1,500 he collected at his bar mitzvah on phone sex, he and Holmes somehow manage to organically fit in frank discussions of the U.S. criminal justice system and the place of humor in the Holocaust.

Jenny Slate (Episode 55, 2012)

At two and a half hours, this is a long podcast episode even by You Made It Weird‘s chatty standards, but it never, ever drags. Highlights include the Obvious Child star’s history of childhood couch masturbation and her rendition of her baritone mom and soprano dad’s “House of the Rising Sun” duet.

Josh Ruben (Episode 210, 2014)

This delightfully silly episode is notable for the sheer number of impressions Ruben and Holmes perform per minute. Among them: Robert De Niro, Philip Seymour Hoffman, Robin Williams, Jeff Bridges, Ray Romano, Matthew McConaughey, Alan Rickman, Eckhart Tolle, Jack Nicholson, and the Tanzanian nun who writes a letter to Jack Nicholson’s character in About Schmidt.

Emily Gordon (Episode 22, 2012)

Writer and former therapist Gordon is one of Holmes’s best friends — and is married to another, comic and actor Kumail Nanjiani, who was himself the first ever YMIW guest. Their warm, insightful discussion digs deep into breakups and relationships, and Gordon opens up about surviving an eight-day coma.

Patrick Walsh (Episode 40, 2012)

Walsh, a consulting producer and writer on Crashing, first became friends with Holmes when they were both hired to write for NBC’s ill-fated India-set sitcom, Outsourced. They reflect on the “Not Feelin’ It” chicken, a beloved inside joke from the set, and Walsh shares a Tijuana strip club story with a Usual Suspects–caliber twist ending.

And five more weird ones:

Harris Wittels Returns (Episode 236, 2014)

The comedy community was devastated when the thirty-year-old Wittels died of a heroin overdose in February 2015. The comic and Parks and Recreation writer and co–executive producer had sat down for an interview with Holmes a few months earlier, in which he was incredibly open — and optimistic — about his recovery and sobriety. Wittels’s account of his misadventures as an addict is harrowing and heartbreaking, yet somehow hilarious, because that was Harris.

Aaron Rodgers (Episode 310, 2016)

Yes, that Aaron Rodgers, Green Bay Packers quarterback. The Super Bowl MVP proves to be a fan of both Halo 3 and the History Channel’s Ancient Aliens, but the single greatest revelation here is that Rodgers is a UFO believer. He describes an unexplained phenomenon he spotted in the midst of a New Jersey snowstorm in dead-serious detail.

Garry Shandling (Episode 299, 2016)

In one of Shandling’s last interviews before his unexpected passing in March 2016, he’s as funny and sharp as ever. Garry and Pete talk fucked-up family dynamics and meditation, which Shandling began practicing at 25. The legendary star of The Larry Sanders Show mentions that he feels accepting of death: “Life is short, but not short enough,” he jokes.

Chris Gethard (Episode 173, 2013)

Once upon a time, Chris Gethard was Pete’s improv teacher at the Upright Citizens Brigade. This episode is great for a lot of reasons, but it gets especially good when the comic and talk show host tells Holmes for the first time ever that Conaco had initially considered him for the TBS slot it ultimately gave to The Pete Holmes Show.

Chelsea Peretti Interviews Pete (Episode 100, 2012)

To celebrate the 100th episode of You Made It Weird, Holmes enlisted “best worst friend” Chelsea Peretti to interview him, asking listener-submitted questions. Listening to the Brooklyn Nine-Nine star abuse her pal is a sublime pleasure, for all parties involved.