Pete Holmes on How to Keep NYC from Stealing Your Soul

Pete Holmes wants to soothe our doubts about self-worth. In his comedy specials Nice Try, the Devil (2013) and Faces and Sounds (2016), he attempted to bridge the gap between the silly and the relatable, with jokes about everything from his erotic love for Ryan Gosling to riding with a flute-practicing Uber driver. Although the framing devices are sometimes absurd, the message is always a positive one: Everything is alright—after all, we've all been in horrible situations before.

That message is also present in his podcast, You Made It Weird, where the 37-year-old Massachusetts native encourages guests to expound on everything from monogamy to whether there's any sort of afterlife. Since coming into his own as a podcaster, Holmes has created a space where comedians, physicists, spiritual gurus, and musicians can open up about weighty, metaphysical concepts and reveal insights into who they fundamentally are.

And as the star of HBO's Crashing, Holmes—along with co-writer Oren Brimer and executive producer Judd Apatow—is looking to soothe an even larger audience while staying true to the realities of struggling as a stand-up comedian. The show follows a fictional version of Holmes as he loses his wife, his religion, and his wallet—and yet it's also an optimistic spin on cringe-based comedy, with a protagonist who wants to hug it out when the rest of the world just wants to be left alone. As he goes from babysitting Artie Lange to (almost) bonding with the man who broke up his marriage, Holmes's character adjusts to the reality of being separated in pieces, with stand-up as the thing that keeps him going.

I recently spoke to Holmes by phone; he was ever amicable, despite a bad phone connection and a dog that was eagerly trying to get his full attention.

VICE: Who came up with the idea behind Crashing?
Pete Holmes: I was having a moment of frustration after my show [TBS's The Pete Holmes Show] was canceled, so Oren and I were trying to figure out what to do next. We were thinking of doing a sketch show, but there was also possible interest in doing a talk show. We took a meeting with Comedy Central—they passed—and after the meeting, I got in my car and asked, "What is something that's really true to myself?" Being raised very religiously, getting married to the first person I'd ever loved or had sex with, and being left by that person was what I had to offer. The idea of staying on a different comedian's couch each episode was an idea that really clicked with me, too—and it tightened the focus.

The idea also seemed Apatow-ian to me, in that it had a "grown-man-growing-up or coming-of-age" quality to it. After I pitched Comedy Central on Wednesday, I flew to New York that Friday to pitch Judd on the set of Trainwreck, and I'm so glad that he thought it was a good idea. Having him onboard was a tremendous help—I'd write, and he'd point out things that either weren't working or could work better if done differently. We kept honing the voice of the show together, and it's been a dream. I wouldn't have pitched him if I didn't think it made sense, so I'm glad it worked out the way it did.

The show feels more like an attempt to replicate reality than an attempt to create a world shaded by your comedic perception.
We tried to build a comedy about my character trying to fit into reality. In a lot of obvious ways, this is not Pete's world, and he's trying to fit into a pretty harsh version of New York. We're trying to answer questions about what pieces of his soul remain intact and what perceptions he needs to let go of. It's the concept of what we're supposed to be, versus what we're supposed to do. If Pete stayed married, he might've lived the safe life of a suburban youth pastor. Instead, he left—and the show is about what difficult and beautiful things happen from that point on.

Was it strange or difficult to relive the collapse of your first marriage?
It felt really good, actually. Going back to some of those feelings is doing some work on my psyche. At times, it feels like a dream, but not necessarily a bad one. There's healing in putting myself through situations on the show that are similar to things I've experienced in the past, because I can write about it from a different perspective. Since those wounds are closed up, I can offer sympathy to certain people in certain situations that wouldn't have been possible in the past.

Honestly, the hardest thing to do on the show was to be honest. As a comedian, you sharpen your skills over time—so to go out in front of 300 people and pretend to bomb required a certain level of emotional commitment. Being true to those feelings and early experiences was difficult, but it was also extremely necessary for making the show work and feel authentic.

At this point in the show, your character is still living with a deep sense of Christian faith. In real life, do you think you needed to let go of that in order to really become a comic?
I needed to let go of the idea of a God who was mad at me for feeling how I was feeling. Now, I bask in an understanding of the divine that delights in truth and the complexities of the human experience—even when it's not very "clean." When I thought being a Christian meant not saying "fuck" and keeping your doubts and dark thoughts to yourself, I had a lot to learn. Now, I believe that trying to follow someone like Christ is a lot more about living authentically, beautifully, honestly, and with love—and sometimes saying "fuck."

The Pete Holmes Show was such a distinctive showcase for both sketch comedy and general comedic ideas in the late-night landscape. What lessons did you take away from the process of making that show?

When you slide into television, no one tells you exactly how manage expectations and work with your staff. I now realize that things like checking in and having meetings are very important. I also learned that it's cruel to be kind—if someone has an idea that doesn't work, it's better to be upfront than let things drag on.

You discuss spirituality a lot on your podcast—particularly the teachings of Ram Dass. As a comic, what speaks to you about the idea of mantras and emotive lessons?
I think there's something so funny about Ram Dass. I was lucky enough to sit across from him at dinner once, and I got up the courage to tell him that he was my favorite comedian. Even though he's not a comic, he talks about showbiz in a certain way and understands that there's a presentation to it. On the one hand, he's a funny, bright, Jewish college professor, which is relatable in some ways—but he's freeing people emotionally, and I identify with that. Good comedy can be liberating, and if I'm doing my job as a comedian, part of the joy for the audience is getting that release.

Eric Farwell's writing has appeared or is forthcoming in McSweeney's,the New Yorker, and the Los Angeles Review of Books.

Crashing airs on Sunday nights at 10:30 PM on HBO.