The 15 Best You Made It Weird Episodes

Comedy Lists Pete Holmes
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9. #332: John Mulaney Returns

Mulaney and Pete go way back, and from their first conversation together it’s immensely satisfying to hear the banter between two friends who have been through the shit together and have both emerged successful (“Do you know about my nightmare show-biz dreams?” “I’m familiar with your nightmare show-biz waking life.”) But all that is basically table-setting for Mulaney’s return episode, which dives into the fallout from his eponymous sitcom and its cancellation. The entire experience was clearly an unmitigated disaster, but Mulaney’s epic rebound, which involved throwing himself headfirst into the ten-year-old act with Nick Kroll we now know as Oh, Hello, demonstrates the perspective you gain when you achieve your dream and it falls flat on its face. Mulaney is both wiser and funnier thanks to that failure, and this episode is proof.

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8. #329: Mike Birbiglia #3

Mike Birbiglia  has an excellent track record on the show (his Pete burns are among the most unexpected and fun), but he is at his best in this thorough deconstruction of his second film, Don’t Think Twice. Pete lost his mind when he saw the movie, and butters Birbiglia’s bread throughout, but it only lends their discussion more fuel. If you’re a fan of Don’t Think Twice, this conversation is a worthy companion piece. Even if you’re not, it serves as an immensely compelling dissection of the sadness and selfishness inherent in pursuing improv professionally—whatever that even means—while still examining the qualities of improv that attract people on stage and in life. Birbiglia is an uncanny judge of his own work, and uses the conversation to go over the whole process with a self aware eye—everything that worked, everything that didn’t work, and how it all came together. If you’re a student of filmmaking at all, it’s a must-listen; as far as this podcast endeavors to examine the intersection between art and life, it’s a series highlight.

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7. #91: Thomas Middleditch

Not all great episodes of You Made It Weird get particularly weird. But when they do? Whoo-boy. Thomas Middleditch (Silicon Valley) and Pete were friends once. And then they weren’t. And neither is entirely sure what happened. But they get together to figure it out, and over the resulting two hours, set things back on the right course. In the meantime, it’s hilarious and incredibly uncomfortable, especially since their beef involves other members of their circle of friends (and some of Middleditch’s future Silicon co-stars). But it’s ultimately touching to watch them work so hard through the awkwardness, remembering old bits (their impressions of Kumail Nanjiani cumming blood in front of Emily Gordon) and creating new ones (“Ev-ery-day Je-sus!”). It’s utterly unique in its discussion of the under-discussed “friend breakup,” and as authentic as a preplanned recorded discussion between friends could possibly be.

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6. #40: Patrick Walsh

If nothing else, the Patrick Walsh episode gave us two beautiful gifts; the “Not Feelin’ It” chicken they invented during their time as staff writers on I Hate My Teenage Daughter (probably the best thing to come out of that show), and Walsh’s epic story of an ill-fated male bonding trip to Tijuana that involves a beautiful Pretty Woman stripper and a single paper towel. It is impossible, I repeat, impossible to build up this story too much. The payoff is that brilliant and unexpected. Thankfully, the rest of the episode is just as wonderful. The two friends spend most of the time remembering their own coping strategies for working on a show no one really liked and they themselves did not respect, but as a result its twice as hilarious as most YMIW episodes.

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5. #173: Chris Gethard

Chris Gethard  has never been shy about his personal life. Pete’s interview with him covers the same general ground as Gethard’s My Comedy Album (the molly-fueled breakup with his girlfriend of eight years, the benefits of regular butt eating) but in way more detail than he was able to go into onstage. In the process, we get a very YMIW twist: Gethard had been approached by Conaco several years back, as Conan O’Brien was interested in picking up the public access version of The Chris Gethard Show. He did not, passing over Gethard’s show in favor of Pete’s. It’s one of the podcast’s weirdest moments, even if it breaks the ice and seems to delight both parties. But it’s Gethard’s honesty about the dissolution of his longest relationship that separates this episode from the pack. He clearly inspires a punk rock, cult-like devotion from his fans, and if you’ve ever been curious as to why, this episode is a great place to start.

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4. #100: Chelsea Peretti Interviews Pete

From here on out, we’re dealing with bona fide YMIW VIPs. Every one of Peretti’s appearances on the show has been memorable (particularly her second episode, where Chelsea and Pete listen to a fan-submitted supercut of every time she had been mentioned on previous episodes, leading to Chelsea’s detailed description of how she would kill Pete, and vice-versa). Nothing, however, beats her appearance on the hundredth episode, in which Pete takes the guest’s chair so Chelsea can riddle him with fan questions. I don’t know what possessed Pete to make him think this would be some kind of celebration, or good for him at all, for that matter, because Chelsea tears him, the fans, and the show to pieces and then makes him put it all back together. Pete could have ended the show right there, and this would have served as a perfect finale. Obviously, we’re glad he did not.

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3. #236: Harris Wittels Returns

On February 19th, 2015, Harris Wittels was found dead of a heroin overdose in his home. He was thirty years old. A few months earlier Pete recorded his second interview with Harris, and, among other topics, they discussed Harris’ most recent struggle with addiction. Though the stories Harris told were extreme, scary and admittedly—in his hands—hilarious, the episode ended on a positive note; Harris was getting help and getting sober. He said he was in a good place, and according to a set he did at the Meltdown the night before he died, he still was. It was the kind of episode that shook you to your core even before his death. After the fact, it’s absolutely devastating. By all accounts, Harris Wittels was one of the funniest people. Period. His episodes of this podcast confirm as much, and additionally introduced us to a warm personality and powerful friend. Plus, I imagine his candidness regarding his addiction helped a lot of people. There’s an early episode of YMIW where Chelsea Peretti gets on Pete’s case for concluding an anecdote about Mitch Hedberg—a man he had never met—with a comically sincere “miss you, Mitch.” Therefore, I don’t feel that weird about ending this lil’ blurb with a “miss you, Harris.”

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2. #334: Bo Burnham #3

Bo “Boom Boom Boom Boom” Burnham is the reoccurring YMIW guest I look forward to most. That said, even he admits that your reticence about listening to the opinions of a twenty-six year old white comedian who became famous for doing musical YouTube videos at sixteen is reasonable. To those people: I beg you to check in with the new Bo Burnham. Not only have his last two specials been absolutely mint, his appearances on this podcast are increasingly jaw-dropping. I maintain that, even among those people who are obsessed with his specials, Burnham does not get enough credit for being such a force of nature in these kinds of interviews. He has something to say about everything, tripping over his own words as he struggles to communicate his thoughts as he thinks them. This should come off as incredibly annoying, but it doesn’t. He delivers a passionate screed that runs through the fall of late night TV, the democratization of content distribution, the culture of selling out, how old white men are the enemy, his own limitations in terms of what he is qualified to talk about, his own unanswered questions, and comedy’s incredible potential over the course of his mammoth three-plus hour third YMIW. He clearly lights up Pete’s buttons to an absurd degree. Until he gets the talk show he does not want, I eagerly await #4.

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1. #197: Moshe Kasher Returns

The first Moshe Kasher YMIW is really, really good. They really get into it regarding Kasher’s years in the Oakland rave scene and give us the helpful definition of “fuck-guy.” The second Moshe Kasher YMIW? I have never laughed harder than I did at the second Moshe Kasher YMIW. If you’ve never listened to the podcast before, this should be your gateway. Once you learn about Racist Stephen Hawking, “welcome to Gringotts,” the Money Meeting, Going Going Gandhi, “Rape is not good for anybody” “You heard it here first, folks,” “he’s ha-sitting there with his ha-hat,” Medium Soup, “you’ll be keeping that,” what a piece of shit Mordechi Ben David is, and the Bar Mitzvah song that ties it all together, you won’t want to go back. But the episode transcends its stellar bits and finds balance. Most of the jokes occur naturally as Pete and Moshe continue to get sidetracked on the road to discussing the other half of Moshe’s childhood (he spent part of his time as a kid with his deaf mother and grandmother while he raved in Oakland, and part of his time with his deaf father in the most extreme of Brooklyn’s Hasidic sects). This was all partially covered in Kasher’s superlative memoir, The Kasher in the Rye, but they dig even deeper here. The result is You Made It Weird’s most dynamic episode—comedically satisfying and emotionally satisfying in equal measure. And it’s Moshe Kasher, so naturally he makes time for a little discussion about the Council of Nicaea and how the prison-industrial complex is the new slavery. Get. In. To. It.

Honorable Mentions

This started out as a list of the top ten episodes but after going through the full run again that proved to be impossible. Still, even after expanding it to fifteen, it felt like some fantastic episodes were getting short shrift. So what the hell, here are a bunch of honorable mentions.

Pete’s produced some great live episodes over the years, although they generally don’t have quite the loose conversational power of in-studio installments. You should check out #33: Live from SXSW with Judd Apatow, Todd Barry & More; you can trace Crashing, Nanjiani’s The Big Sick, and Gethard’s Career Suicide back to this appearance with Judd Apatow. #83: Live From SF Outside Lands! is easily the most uncomfortable thing I’ve ever heard in my life.

There are some great fuckaround episodes in addition to the ones listed above. #210: Josh Ruben, in which Josh and Pete just attempt impressions the entire time, is so entertaining that it warranted its own re-release. Early episodes featuring Neal Brennan, Anthony Jeselnik and Nick Kroll set a good precedent for the guest shitting on Pete. In #9: Sarah Silverman, we learn exactly how many pumps it took for Pete to lose his virginity.

Though it’s now more of a footnote to his career than anything else, Pete’s years submitting cartoons to the New Yorker are fascinating, and #18: Matt Diffee & Alex Gregory, a conversation with two New Yorker cartoonists, is an insider’s look at a hyperspecific world within comedy. #303: Bruce Eric Kaplan explores that topic further.

While You Made It Weird is at its best when other comedians are involved—and this list reflects that—Pete’s curiosity has produced some great episodes with scientists, musicians, writers, spiritual folks, etc. Check out the episodes with Ben Folds, Glen Hansard, Henry Rollins, Brian Greene: Theoretical Physicist and Rob Bell for more on that. Keep It Crispy.

Graham Techler is a New York-based writer and actor. Follow him at @grahamtechler.

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