If you’re just now learning about Pete Holmes from his new HBO sitcom
, you have a lot to catch up on. For instance: there are 350 episodes of his Nerdist podcast You Made It Weird. Here are the 15 best.—Ed.
has fully admitted—multiple times—that his podcast is a nice-boy ripoff of Marc Maron’s. The What the Heck? to his What the Fuck? But though Maron may have created and popularized the interview podcast—and, let’s be fair, redefined the long form interview itself, in the medium’s first dramatic update since Dick Cavett—Holmes was the one to personalize it, adding considerable breadth and depth to Maron’s already overshare-prone format. You Made It Weird covers an astounding amount of ground, even within its Comedy-Sex-God format. And Pete’s ability to spark up chemistry with anyone delivers spontaneous, conversational comedy in episodes with close friends and obscure strangers alike.
YMIW has its fair share of detractors—Holmes’ best frenemy Chelsea Perretti vocally abhors the pet name “Weirdos” and I know plenty of people who love Holmes in general but can’t get on board with his distinctive belly-laugh—but the people who love this show love this show, and consider it to be Pete Holmes’s purest possible expression of Pete Holmes.
With Holmes’s new HBO sitcom Crashing pulling in rave reviews, Paste has decided to look back on all 350-odd episodes of You Made It Weird in order to pick the top fifteen (we couldn’t pick ten). These are the sweetest, the funniest, and the overall weirdest.
15. #2: TJ Miller
The earliest episodes of YMIW stuck strictly to Pete’s inner circle, and they tried to adhere to the show’s original format, where Pete brings up three weird things he knows about the guest. From the get-go, you could tell that both Pete and the guest felt limited by this premise. He wouldn’t abandon it completely until later, but his first interview with a mostly pre-fame T.J. Miller offered proof that YMIW could do full episodes where they just pal around doing bits without it becoming solipsistic or self-indulgent. In fact, it’s delightful! Miller’s later appearances are fascinating as well (he returned in another early episode to explain his feud with Dane Cook, and then again several hundred episodes later to aggressively challenge Pete on questions of nihilism), but he’s at his most playful here, getting on Pete’s case for his “Springs and Sponges” theory and telling the gripping story of his cerebral arteriovenous malformation on the set of Yogi Bear 3D.
14. #300: The 300th Episode
Pete sits down for the 300th episode of YMIW to drink and answer Twitter questions with his opener and friend Brent Sullivan (also the subject of his own fantastic episode). But this episode is most notable for being the first significant on-mic appearance of Pete’s frequently referenced girlfriend Valerie. It may seem cheesy and overly narrative, but fans had heard so much about Valerie up to this point, and had become so invested in Pete’s romantic life after hearing the story of his divorce (many, many times) that when Valerie finally showed up, and their relationship was as sweet, communicative and passionate as we had hoped, everyone flipped a shit like it was the end of The Parent Trap. It goes without saying, but Sweet Lady Val is a wonderful guest in her own right; charming, whip-smart, and completely holding her own against the two loud, drunk comedians who, of course, happen to be her best friends. Plenty of YMIW episodes have a “hangout” vibe that makes one envy that time in the studio, but this was the first episode that made people want to be Pete and Valerie’s dog. If that sounds a little weird, it fully is!
13. #67: Jerrod Carmichael
Pete’s often referenced this episode as an early example of how a guest can blow his mind, and it’s not hard to see why. Our minds are blown plenty, too, as Jerrod Carmichael ups the ante on the podcast from self-reflection to full-on show-biz philosophy. This episode was recorded before Carmichael had begun to break into movies and TV—he was only twenty-five at the time—and his Zen thoughts on the nature and purpose of being a comedian would come off as premature if he wasn’t so assured and on-point. Their conversation audibly fills Pete with creative energy and has a similar effect on the listener; it is an essential podcast episode for anyone pursuing a career in any kind of creative field, especially comedy.
12. #22: Emily Gordon
Roughly twenty episodes after interviewing Kumail Nanjiani, Pete sat down with one of his best friends, Nanjiani’s wife Emily Gordon. This episode introduced us to YMIW’s confidence that a great episode didn’t need a celebrity guest. Pete and Emily’s relationship is captivating by itself; her background in therapy makes her someone Pete frequently seeks out for help, and her marriage with Kumail makes her the perfect person to address one of the podcast’s self-stated themes; who is right for a comedian? Plus, this episode contains one of the most heartbreaking and romantic stories ever covered on the show—the coma Emily fell into early in her relationship with Kumail, and how it set the stage for their marriage. Emily would later join her friends and husband’s profession, and has proven herself to be as talented as anyone in that circle. But it’s still immensely refreshing to hear a comedy podcast feature someone—at the time—who could give a third-party perspective on the community and its ambitions. Moreover, when you think about Emily-Kumail-Pete as a triad, and Valerie-Pete-Brent as a triad, this episode is crucial in recording the narrative of Pete’s life, and the podcast’s general reflection on how friends form a family.
11. #44: Dana Gould
We can look back on Dana Gould’s interview as a landmark YMIW episode just based on the running time. It was the first episode to crack two hours, and certainly not the last. When Pete stopped caring about how long the podcast ran, it took a palpable step up, and the level of detail in this episode reflects Pete’s relief in being able to run off on tangents and pick Dana’s brain as much as he wants. Pete is in full fanboy mode here, as Dana waxes nostalgic about his time writing for The Simpsons. Their conversation somehow avoids any semblance of Fallon-ness. It’s just pure, geeky fun. Pete throws his favorite Simpsons bits (“What’s for lunch tomorrow?” “Next!” “Chicken necks?”), Dana fires back with anecdotes from the writer’s room (“I want to wreck something. Not havoc…”) He also delivers some genuinely sweet stories about his interactions with celebrity, including a sentimental moment of confirmation from Elvis Costello. Any podcast that confirms the myth of Elvis Costello is okay in my book.
10. #299: Garry Shandling
This was one of the last in-depth interviews Garry Shandling did before his death last March. I would almost argue that it’s better to listen to Pete’s re-release of this episode from shortly after Shandling passed away. The somber introduction makes their chipper conversation a little eerie, but it’s crucial listening for those fans who crave some posthumous advice and guidance from Shandling—he was well-known as a sort of reclusive comedy guru after completing The Larry Sanders Show. In a later episode of the podcast, Judd Apatow notes that Shandling thought long and hard as to whether he had another story to tell, and decided he did not—this is the closest possible thing. Parts of their conversation remind me of the time Harry Potter talks to Dumbledore in limbo. It’s deeply sad and more than a little unsettling, but it also gives the listener a definitive final talk with a man who was kind, funny, experienced, and had clearly achieved some form of enlightenment.