Why Pete Holmes' Prior Work Bodes Well for HBO's Crashing

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Most comedy fans were probably introduced to Pete Holmes through his Nerdist podcast, You Made It Weird. The show features an interview format roughly divided among three topics: comedy, religion and sex. The guests are usually comedians of different stripes, with a handful of notable exceptions, such as Noel Gallagher of Oasis or motivational speaker and Holmes collaborator Rob Bell.

Holmes, whose new HBO series, Crashing, premieres Sunday, is a non-threatening goofball with an over-exuberant laugh—an aural indication of his commitment to embracing the humor and happiness of everyday life. The whole of Holmes’ work, in particular the thread of benevolence he weaves through it, suggests that he’s poised to produce a TV series distinct from the usual half-hour comedy from a stand-up/auteur—one thoughtful about, and subversive of, the toxic masculinity that permeates certain corners of the comedy circuit, and television, too.

Equal parts inside baseball for comedy and audio evangelism for his New Age, mindfulness-based personal philosophy, Holmes’ podcast premiered in 2011, and its quality and longevity have cemented its place in the fast-growing podcast marketplace. What makes Holmes’ podcast great is simple, and it’s what makes any podcast great: the feeling that you’re listening to an intimate, interesting conversation between two people you wish were your friends.

An especially fitting example of how You Made It Weird’s conversations blend comedy and personal introspection in a way that feels endlessly wise is “John Mulaney Returns,” in which Holmes talks on the podcast with his friend, another successful comic and former Saturday Night Live writer, for the first time since Mulaney’s Fox sitcom flopped in spectacular fashion. “[It] didn’t go your way,” Holmes says. “It didn’t go any way,” Mulaney replies. “A critical and commercial failure.” Given how highly regarded Mulaney is as a comedian—and how well he’s done for himself since the cancellation of Mulaney in 2015—it’s all the more illuminating to hear how he bounced back firsthand. When someone that so many people like and look up to manages to recover from a stinging failure, it makes a listener feel more secure in the ebb and flow of her own weird life.

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There isn’t much room for calculated criticism of social norms in unscripted conversations, but You Made It Weird creates a 338-episode backlog of the authentic enthusiasm that permeates Holmes’ other work. In his stand-up and on the podcast, Holmes manages to be both goofy and earnest by satirizing the toxic and fragile masculinity of his everyday life: He’s earnest about being goofy and goofy about being earnest. Holmes’ formal stand-up catalogue is comprised of two albums, including his first hour-long special, Nice Try, the Devil. His stand-up oozes an exuberance that’s hard to ignore. It also features a long-standing signifier of quality: punching up. Holmes tends to aim his comedy in the direction of straight, white men like himself, and much of his observational style focuses on the general foolishness and odd behavior that masculinity shoehorns them into. This quality of Holmes’ comedy makes him easy to like because it’s self-deprecating, without being so negative as to be dull.

Take, for instance, a joke from Nice Try, the Devil called “Gay for Gosling”: The crux of it is something Holmes calls “The Price Game,” which involves asking his straight friends how much money they would need to go down on another man and marveling as they refuse, no matter the amount, in an attempt to try and remain “macho.” “$100 billion a week for life? ‘Not even considering it, bro!’” Even when the stakes are raised to hypothetical extremes, such as saving one’s sick mother’s life, Holmes’ interlocutors still won’t budge: “Ma didn’t raise no homo, just an irrational monster who won’t save her.” While jokes about “being gay” for any particular individual usually aren’t funny, Holmes avoids this trap and instead treats the rigid, fearful sexuality of straight men with the hyperbolic mocking it deserves.

Holmes is naturally silly, and his comedy is marked by an ability to find joy in innocuous moments. His most recent stand-up special, Faces and Sounds, which aired on HBO in December, is a meta look at how Holmes’ joyful approach to life affects his identity as a white man, his work as a comedian, and the way he moves through the world. This is exemplified by a wonderful joke from Faces and Sounds about a TSA agent with a strong reaction to a Green Eggs and Ham T-shirt Holmes frequently wears when he travels—wherein the agent candidly asks Holmes, at 7:30 a.m., what he knows about green eggs and ham. “Is that a security question?” Holmes asks excitedly. “Who are green eggs? What is ham?” That Holmes can create a genuinely funny bit out of a TSA experience that doesn’t involve complaining about the TSA speaks volumes about Holmes’ optimism. If his jokes sound simple, it’s because they are. That’s part of their charm. He’s able to delight in the ordinary as well as use it to combat the negativity people encounter on a regular basis: For example, he advises audiences to lob the Green Eggs and Ham question at the next person to steal a parking spot from them.

Crashing is Holmes’ second time at the helm of a TV show, after his late-night program The Pete Holmes Show, which ran for two seasons on TBS in 2013 and 2014. Holmes developed the show with Conan O’Brien, whose own revamped talk show moved to the network three years prior. It was Holmes’ take on a late-night show, featuring interviews, stand-up sets, and a variety of running segments and sketches that highlight the same irreverent enthusiasm for goofy pop culture references—including a sketch called “Ex-Men” about X-Men getting fired and a bad/weird Batman impression—that defines his stand-up. It also featured a cute recurring interview segment called “Gabbing Like Gals,” in which Holmes sat in a slumber party set-up, pajamas included, with female guests.

The segment isn’t meant to poke fun at how women relate to each other, but rather to highlight the fact that Holmes is so excited to interact with them in a way men usually don’t want or aren’t able to. When YouTube personality Grace Helbig appeared on the segment, Holmes introduced it by admitting he likes “gal things” like ice cream and face masks. If his “Gay for Gosling” joke is any indication, these are things most men are too proud to admit they enjoy, let alone ask an actual woman about. In Holmes’ worldview, most men are too “cool” to care. He (and the segment) fly in the face of that position.

Crashing is based on Holmes’ real-life experience, namely his ex-wife’s extramarital affair and their subsequent divorce. The premise itself might seem a little tired and could be handled with misogynistic contempt by someone else, but there’s no male comedian I trust with it more. During Mulaney’s first appearance on the podcast, Holmes reveals an unreserved lack of bitterness, saying he doesn’t harbor any hate or anger towards her, mostly due to the fact that his career took off after his divorce. A show premised on a worst-case scenario (Crashing’s tagline is “He’s lost everything but his sense of humor”) also necessitates a lead character whose redemption arc audiences will actually care about. Holmes’ fits the bill as a thoughtful and aloof everyman embracing the admittedly shitty hand he’s been dealt.

While “ladies trying to make it in the big city” is well-trodden territory on TV, a man getting the rug pulled out from under him is decidedly less common. By laying the groundwork for a TV series that allows a male protagonist to be vulnerable—even if it’s not by choice—Holmes is doing something different. Admitting defeat (especially sexual defeat) and asking for help are two deeply vulnerable acts that toxic masculinity tells men are “unmanly.” Using that as a premise for a TV series disrupts the script of masculinity: Portrayals of men engaging with their emotions in a way not dictated by those scripts—which Holmes so often skewers in his work—are on the rise, but they’re still rare enough that their appearance deserves notice. Of course, the half-hour TV comedy is a shorter and perhaps less flexible format than the hour-long stand-up special or the two-plus hour running time of many of Holmes’ podcast episodes, but it allows for the use of new narrative devices to deliver the joy and emotion that make Holmes’ work so compelling—as well as forcing them to be more concise and, hopefully, more powerful.

While I re-watched Faces and Sounds to finish this piece, Jeff Sessions was confirmed as Attorney General. This is to say that it’s a scary time and place to be alive. Finding joy wherever we’re able is of vital importance, and Holmes is an exemplary coach. In a world where fragile masculinity is now a matter of national security, the portrayal of a straight, white man who takes his vulnerabilities in stride will be refreshing, reassuring, even necessary.

Crashing premieres Sunday at 10:30 p.m. on HBO.

Tallyn Owens is a young professional and writer living in Washington, DC with a dog named after Peggy Olson. Her writing has previously appeared in Paste andThe Establishment. You can find her tweeting about TV, basketball and abortion at @TallynOwens.

Why Pete Holmes’ Prior Work Bodes Well for HBO’s Crashing