15 of the Weirdest Moments Pete Holmes Has Had on ‘You Made It Weird’
Pete Holmes brings the same high-energy approach that defines his standup act to his podcasts, almost daring his interview subjects to match his candor in the conversation. And it works; most guests get caught in Holmes’s wake and find themselves admitting as much or more about themselves than he does.
Holmes often jokes about “stealing” Marc Maron’s podcast format, which is true to the extent that they both do in-depth interviews with comedians. The similarities really end there, though, because Pete Holmes and Marc Maron are two very different comics and conduct very different interviews. In the 100th episode of You Made It Weird, in which Holmes had his friend and fellow comic Chelsea Peretti interview him (a tactic that, fittingly, was first used for the 200th episode of Maron’s WTF podcast), Holmes paraphrased a listener’s description of what makes You Made It Weird unique.
“The main difference between WTF and this show is that Maron refers to himself as ‘Maron,’ and I refer to myself as ‘Old Petey Pants.’”
Holmes has said that the interview segments of The Pete Holmes Show, premiering this Monday on TBS, will emulate the podcast, so naturally the podcast is where most people will get to know him before the show airs. These episodes are some of the best, but the list focuses more specifically on the individual moments within them that make You Made It Weird, well, weird.
Episode 1: Kumail Nanjiani
In the inaugural episode of YMIW, Holmes enlists his long-time friend Kumail Nanjiani to discuss the differences between the comedy scenes in New York and Los Angeles, with Nanjiani talking about advice he reluctantly accepted from fellow comedian Eddie Brill that led to the onstage persona that he still embodies today.
At one point, however, Holmes gives an interesting glimpse into at least part of the reasoning behind his decision to launch the podcast.
One recent girlfriend was very adamant that I was a narcissist. No one has ever called me a narcissist, but like, she really convinced me. That’s kind of like what I’m trying to do, is get over some of the things that this person told me, that I was like very self-centered and very narcissistic. I’ll admit that I’m self-centered, all of us are, but I can also be external and giving and listening and empathetic and all that sort of stuff.
It kind of comes out of nowhere, after Kumail discussed how the show business has affected Kumail’s relationship. It’s unclear exactly what Holmes is referring to when he says this, but given some of the things he talks about in the podcast, it’s a fitting description for his podcast. And Kumail was the perfect person for him to tell this to, because he shot him straight about why someone might get this idea about him – Pete’s need to be liked by everyone.
Episode 135: Dane Cook
Holmes definitely puts in an effort to ease Cook into a comfortable-enough place to share how he feels about a lot of controversial topics. And it works. Cook very politely answers questions about his family, from hinting at alcohol and abuse problems with his father to discussing how he was affected in every other way than financially when his brother stole about $14 million of his money. Cook also addressed how he handled the period in which he experienced a “backlash,” as he described it, from the comedy world.
Episode 96: Zach Galifianakis
In an interview this summer with The AV Club, Holmes said Galifianakis told him after recording the interview that he had actually planned to give him fake answers in the interview, but ended up having a genuine conversation instead.
The sincerity comes through in the episode, which covers a lot about Galifianakis’s views on fame and how he laments what it has done to other comedians, to the point that he admits that he’s considered taking a break from show business. Galifianakis discusses the negatives of his post-Hangover fame, like dealing with teenagers recording video of him while he was in a public bathroom. But he also discusses the highs it has earned him – Holmes relays a story he’d heard about Galifianakis, shortly after hosting SNL, walking down the Brooklyn Bridge and high-fiving strangers who passed him by, and Galifianakis doesn’t deny it.
Episode 139: Bert Kreisher
Holmes explained in that same AV Club interview that he didn’t know Bert Kreisher before the interview, but invited him on the show after mutual fans suggested that their similar energy and boisterous laughs would make for a good combination. They weren’t wrong.
A couple of great moments ensue. Holmes and Kreischer challenge each other to fake laughter together until they start actually laughing. Even Katie, the show’s typically unspoken producer, can’t hold back from laughing.
They raise the stakes, though, when they queue up pop songs they don’t know very well and try to guess the lyrics. It’s starts off pretty well with Celine Dion, but closes out strong as they both sing along to Ke$ha’s “Die Young”. During this, it almost sounds like there are two Pete Holmeses in the room when Bert starts screaming “there you go Pete. We’re gonna die young baby! Does this not make you want to fucking live and get in a Vespa and drive around Venice?”
Episode 12: Anthony Jeselnik
Jeselnik had just gotten out of his relationship with Amy Schumer when he recorded his episode, and was open to discussing it on air. When it’s first mentioned, Jeselnik seemed reserved, saying only that he had just gotten out of a relationship with a comedian. Even Holmes wonders out-loud how he was going to handle that issue on-air.
Soon after, though, Jeselnik opens up and identifies Schumer by name, discussing the issues that can arise when two professional comedians date. Holmes and Jeselnik then go on to commiserate about being “serial monogamists,” and discuss how they are both hoping to spend some extended time single, which neither of them had really done before.
Episode 75: John Mulaney
John Mulaney makes his episode weird from the top, immediately calling Holmes out for talking with a new show-business politeness when mentioning other comedians, which only a long-time friend would notice and make fun of him for.
Later, Holmes describes how Mulaney helped him through his divorce, including a pretty heart-breaking story about how Holmes’s ex-wife left him alone on his birthday, and the awkward way in which Holmes told Mulaney that he was getting divorced.
Episode 49: Bo Burnham
Holmes and Burnham discuss the role of sexuality in comedy, from the discrepancies between masculinity and femininity in comedy to the changing nature of writing jokes about homosexuality into an act. This strikes a chord with Holmes, sparking an interesting conversation about the traditional “boys club” of comedy and how it’s affected them.
Burnham’s a good fit for the podcast, driving a conversation that forces Holmes to outright admit that he’s uncomfortable talking about a lot of the issues involved with it.
Episode 7: Neal Brennan
Holmes opens the podcast with what basically everyone wanted to hear — his ridiculous impression of Dave Chappelle yelling at Neal Brennan, in front of Neal Brennan.
Brennan hates it, of course, which makes for a pretty funny introduction to a thoroughly interesting discussion. Holmes prods Brennan for some of his interesting Hollywood stories, and is rewarded with stories about Eddie Murphy, Paul Mooney, and Dave Chappelle. At one point, Brennan discusses his disdain for the alternative comedy crowd’s incestuous comedy culture, and the common issues that plague comics who don’t diversify their acts for other crowds. This makes for good discussion, because Holmes is highly regarded in the alt comedy scene, but seems to share some of his sentiment.
Episode 4: Dave Coulier
Dave Coulier, famous as Joey Gladstone on Full House, told Holmes a really interesting story about his audition for Saturday Night Live in the mid-80s, the confusion about whether he was hired to the cast or not, and how his ultimate rejection from the show ended up working in his favor, professionally speaking.
Coulier also reveals the origins of the “cut it out” bit he employed on Out Of Control and later made famous on Full House.
Episode 173: Chris Gethard
Gethard was Holmes’s improv teacher at the Upright Citizens Brigade in New York, so he has some really interesting stories about a young Pete Holmes as he was just entering the comedy world. Holmes admits that Gethard, in teaching the class, inadvertently helped him get through his divorce simply by giving something to focus his efforts on.
The best moment of the episode, however, comes when Gethard reveals to Holmes for the first time that he was approached three years earlier by executives at Conaco Productions to discuss turning The Chris Gethard Show into a TV show on TBS. In the story, Gethard says that both Conan O’Brien and Jeffrey Ross encouraged him to continue working on The Chris Gethard Show, which made him optimistic that Conaco might pick up his show later on. Given that Conaco instead picked up Holmes for a TBS talk show, that on-air revelation makes for a really weird, personal moment between two old friends.
Episode 100: Chelsea Peretti interviews Pete
Many mocked Holmes for switching to the interview chair for his 100th episode, and it wasn’t only because of the similarities to Maron and WTF. Holmes doesn’t shy away from talking during the interviews, treating them more as two-way discussions with friends than a Q&A. Especially in the earlier episodes, he went into detail on every sensitive subject of his life, leaving many to wonder whether his contribution as an interviewee would be any different than the stories he’d told in the past.
As it turned out, he had a lot more to say. While discussing his divorce, as he does very casually in almost every episode, he at one point admits bluntly that it’s still painful to him. Peretti seems genuinely surprised at this, which is impressive considering how well they know each other. It’s unclear whether he’s admitted this in the past, but even if he had, it’s a great unexpected moment in the podcast.
Episode 14: Marc Maron
When Maron and Holmes finally clear the air about a perceived podcast “feud,” they downplay any conflict in the similarities and instead acknowledge that YMIW is more of an homage to WTF, made unique by Holmes’s personal approach. In the process, though, they each give a glimpse into why they continue to podcast and what they get out of it.
Maron discusses the benefit of having genuine conversations with people who interest him, which he says he did on a daily basis while living in Boston and New York when he was younger. Implicit in these stories is the fact that podcasting provides a structured medium through which Maron can seek out people who interest him on a broader scale and spend time listening to what they have to say.
Holmes, meanwhile, focuses more on podcasting as a tool to connect with his audience by opening up to them, as opposed to performing in front of them.
“Isn’t that what the whole podcast is? Like, a lot of this is me putting this stuff out there to let a counsel look at it, like a group of strangers look at it, and just be like ‘is this that strange?’ I grew up Christian, I’ve only slept with five people, this, that or the other, I’m codependent, I’m anxious – whatever you want to say, and then you put it out there and then you kind of feel a little more ‘citizen of the earth.’”
Episode 2: TJ Miller
In this outstanding standup set for the Comedy Central show This Is Not Happening, TJ Miller tells the story about the seizures he had on account of a neurological condition, for which he later received surgery. Prior to the seizure, he said that a lot of his friends had noticed that he had been behaving erratically, and many had just assumed he was getting into weird drugs.
In his YMIW episode, it seems that Pete Holmes was one of these people at the time, as he seemed to still believe that partying had something to do with Miller’s condition. So Miller tells the story in full, which would later end up more polished as a standup bit, and explains how his drinking, lack of sleep, and time spent watching Paul F. Thompkins comedy videos may have actually saved his life.
As a little bonus weirdness, Miller decides to turn the tables on Holmes and call him out for taking a writing job on the quickly cancelled NBC sitcom Outsourced. It’s kind of an emotional moment, with Miller showing tough love by simultaneously telling Holmes that he’s wasting his time writing and that he thinks he could be an “iconic” standup comedian.
Episode 83: Live from SF Outside Lands, featuring Eric Andre, Jackie Kashian, Jon Glaser, and Brett Gelman
Holmes has described this episode as “hands-down, the weirdest, weirdest, weirdest episode of this show that’s ever been recorded.” The crowd never seemed fully committed to the episode, which several of the performers pointed out after early jokes fell flat.
A few minutes after introducing Jon Glaser for his segment, Holmes blurted out that the two of them were the final two candidates up for the E-Trade talking baby commercials that Holmes ended up doing for years. Glaser resented that Holmes mentioned it on-stage and said that he “100 percent” regretted agreeing to do the podcast. Holmes apologized earnestly, but it didn’t really end until Glaser addressed the situation to the crowd.
Somehow, though, the show managed to get even weirder from there. During Brett Gelman’s segment, Eric Andre makes a call-back to an earlier joke about Morgan Freeman, and Gelman calls him out for interrupting him. The two of them end up in a full-blown argument on-stage, with Holmes trying to mediate, Glaser taking Gelman’s side, and Kashian trying desperately to get through the rest of the show. By the end, everybody hugs it out, and Gelman asks if Holmes is even going to release the episode. In retrospect, it’s really impressive that he did.
Episode 22: Emily Gordon
When Holmes interviews Emily Gordon, his close friend and the wife of Kumail Nanjiani, he gets into territory that his interviews with actual comedians can’t really access – discussing what it’s like being married to a standup comedian. They talk about her role as a “maternal” figure to not only Holmes but also many of the comedians he and Kumail hang out with.
Combine this with Holmes’s tendency to discuss his relationships on the podcast, and the first half of the podcast is a pretty intense conversation between two friends. It shifts back toward interview territory when Holmes discusses the coma Gordon suffered through years earlier, and how it affected her relationship with Kumail (they moved from Chicago to New York together shortly after she recovered). They also touch upon Gordon’s own divorce at a young age, a topic with which Holmes relates to pretty well.