Winni Wintermeyer

In the lobby of the Bowery Hotel, celebrities trying to look inconspicuous are practically part of the décor. Within a minute of arriving, I nearly hip-checked Dustin Hoffman by reception. But Pete Holmes was impossible to miss. For one thing, he’s tall. Really tall — just a hair under six foot six. For another, you can now spot the comedian’s likeness on the innumerable subway ads around the city for Crashing, the warmly received new HBO series he created and stars in. And for a third, Holmes is nothing if not present, with an easy laugh and an easier grin.

Before Pete Holmes wanted to be a comedian (and before he became host of the popular podcast You Made It Weird, a New Yorker cartoonist, and the erstwhile voice of the E-Trade Baby), he wanted to be a youth pastor. He attended a Christian college, where he performed Christian improv and Christian sketches and sang in the gospel choir. He married, at the age of 22, the first woman he’d ever dated. He pursued comedy. She cheated. They divorced when he was 28. Then a wide-eyed fan of televangelist Joel Osteen, he smoked pot for the second time ever in the aftermath of their split, with friend T.J. Miller.

We met on February 14, Valentine’s Day. “I’m happy to say I almost forgot, meaning there’s no pressure from Valerie,” Holmes said of celebrating with his fiancée, Valerie Chaney, a former middle school teacher who now works for the girls’ empowerment program REALgirl. “Two years ago, we got stoned and watched Fifty Shades of Grey in the theater.” The couple were now set to catch a flight back to L.A., where Pete moved from New York City in 2010 — if they felt up to it when they got home, Holmes said, they might get high and walk to a theater playing Fifty Shades Darker. “Which is really just black,” he observed.

For as long as there have been TV comedies, there’s been no shortage of shows about comedians: The Jack Benny Program in the Fifties, It’s Garry Shandling’s Show in the Eighties, Seinfeld in the Nineties, Louie right now. But Crashing cruises at a much lower altitude of fame, wealth, and stability. It revels in its main character’s suffering: “A lot of the show is taking real, painful things and then getting laughs out of them,” Holmes told me. “If that’s not the meaning of life, I don’t know what is — somehow alchemizing discomfort into something funny.”

Pete Holmes (that is, Real Pete) loosely based Crashing and the same-name character he plays (that is, Show Pete) on his own life: A struggling comic from a religious upbringing is supported financially by his wife, until she leaves him. Broke and homeless, he crashes on the couch of one comedian after another — among them Miller, Artie Lange, and Sarah Silverman as (sort of) themselves, acting as Show Pete’s unlikely spirit guides — and throws himself into comedy like a sacrificial virgin into a volcano.

Crashing isn’t a sitcom. It’s a comedian’s coming-of-age story, with real stakes (Show Pete gets stabbed in the pilot, and that’s somehow not the worst thing that happens to him in the course of the episode) and a sweetness born of Holmes’s goofy, earnest charm. In the first episode, Lange — who lends his name to its title — sits Show Pete down in a pizza place and gives him an unvarnished warning about the rocky path ahead, a monologue the veteran comic improvised. “There’s something about Pete. Like, his face. It’s almost like Opie [from The Andy Griffith Show],” Lange told me of shooting this scene. “You want to help him. And you want to say, ‘Look, pal, if you stay here, this could happen to you. Maybe you should go home and work at a gift shop or something.’ ”

“The show is about people who have a dream,” executive producer Judd Apatow told the Voice. “So it’s not about a successful comedian, it’s about how hard it is to break in. In order to become a good comedian, you have to go through being a bad comedian. You only learn by being bad, and suffering, and doing hell gigs. And then you slowly figure it out. So this show is about that period, which is something that I’ve never seen before.”

The life of a fledgling funnyman is portrayed as much more monastic than glamorous, especially once Show Pete starts “barking,” passing out flyers for hours at a time to attract paying customers to a club in exchange for stage time. The Crashing production team even re-created the “horrible” Boston Comedy Club, which once stood on West 3rd Street — about a ten-minute walk from where Pete and I were sitting — and remains notorious among a generation of comics who came up in New York City. “Something died in there,” Holmes said.

But there are also glimpses of joy to be found. “People used to think I was on drugs, because I was so thrilled to be there, whatever they asked me to do — open up the club or sweep up or anything. I couldn’t believe that they were letting me perform,” Holmes said. “I really try and maintain that, that little burning ember at the bottom of my essence. I still want to be that kid who handed out flyers for five hours, [then got to perform] for five minutes at 1 a.m. on a Tuesday and walked home like my feet weren’t touching the ground.”

After graduating from Gordon College, 25 miles outside Boston, the Massachusetts native moved to Chicago to perform improv but became absorbed in the stand-up scene there instead. Once he felt he’d “hit the ceiling,” Holmes left for New York in 2004, inspired by an interview he’d read with Dave Chappelle. As Holmes remembers it, Chappelle laid out a simple argument for New York City stand-up: “In Boston you go up once in a night. In New York you go up three or four times a night. Who’s going to get better?” Holmes describes the city as an “essential” proving ground for comics; he spent six years honing his skills before heading west to explore TV. “A lot of guys, whether it was for weather reasons or otherwise, would go to L.A., and I think they skipped a step,” he said.

For Show Pete’s stand-up sets, Real Pete repurposed material he’d written and performed in that tumultuous period of his life. But sometimes while they were shooting, even though he was supposed to be bombing, the jokes would work. Apatow had a solution: He’d have Holmes perform the same set “again and again and again,” in front of the same audience. “No matter how good a joke is, no one’s going to laugh a third time,” Holmes told me.

Of all the episodes from the comedian’s life re-created in some form on the show — his wife’s infidelity, say, or telling his parents about the divorce — the most excruciating to relive was dying onstage. “If you’re a performer and you see a crowd of people, you want to do well,” he said. “Even though they’re paid extras, they start to turn in this weird way. You still feel shamed, somehow.”

Nor did Holmes lack for similar experience on an even bigger stage, having hosted a late-night talk show on TBS from 2013 to 2014 that fell victim to low ratings after eight months. Before it was canceled, though, Apatow appeared in a sketch that foreshadowed their collaboration on Crashing. The premise: Pete comes to Judd’s office with a series of increasingly terrible movie pitches, most of them centered on animal magicians. Except one:

“There’s a man, he’s 22, he gets married because he’s religious. And then six years later his wife cheats on him with a small Italian man, and then I get my heart broken, but I learn life lessons,” Pete says in the pitch.

“That doesn’t seem like a comedy at all,” Apatow deadpans in response. “That just seems tragic and sad.”

Photograph by Winni Wintermeyer

Unsurprisingly, it took some time before Holmes could see his divorce as anything other than just that. A friend, actor Brian Sacca, suggested that it might make for a good one-man show one day, though for about a decade Holmes failed to recognize the fodder beyond its potential for informing a “cartoonish revenge piece.” But after the demise of his TBS show, Holmes was shopping a sketch program when the idea for Crashing finally came together on the drive home from an unproductive meeting at Comedy Central. Two days later, he flew to New York City to pitch it to Apatow on the Trainwreck set.

With the passage of time, he could write the other characters with empathy and compassion and imply that Show Pete was already having an affair of his own: with comedy. Holmes approached adapting his memories like “writing a myth” — keeping more loyal to the emotions than the facts of what happened. “The literal truth is your wife leaves you and it’s all in slow motion,” he reflected. “You have all these long, drawn-out conversations and there’s a lot of alone time and eating ice cream. And that’s not very funny or interesting.”

For example, on Crashing, Show Pete performs stand-up just hours after his marriage falls apart. Real Pete didn’t do that, but he did take a meeting with an agent the next day, which he’d been looking forward to for months. It did not go well. (“I would love to have footage of that meeting,” Holmes laughed. “Because you can feel it on people: Something’s wrong in your life. It’s like a heat or something. And he did not sign me.”) Most surreally, Holmes — a vegan and a committed practitioner of meditation — found himself reconceiving the man his wife left him for (named Leif in the series) as a version of his present-day self: a hippie who reminds Show Pete that this is all “grist for the mill.”

That happens to be the title of a book by Ram Dass, the New Age spiritual leader and onetime Harvard professor, who figures prominently among Holmes’s off-the-beaten-path set of influences. There’s also Osteen (whom Show Pete listens to in his car) and — speaking of myths — scholar Joseph Campbell, whose writing on mythology is a frequent touchstone for Holmes. In describing Show Pete’s “hero’s journey” into comedy, Holmes cites a favorite Campbell line: “The cave you fear to enter holds the treasure you seek.”

Every comedian is “seeking something,” Apatow says. “They’re trying to figure something out, which is why they perform, because they’re communicating with other people what their journey is and what they’re learning along the way. So there’s always been a connection between spiritual thinkers and comedians.

“You know, a lot of comedians have their doubts about God — they’re typically skeptical, and that’s part of the job. So to have a lead character who fully embraces religion, it makes him a funny comedy team with anyone else he’s talking to.”

In Lange’s experience, too, churchgoing comics are a rare breed: “If they’re religious, it’s usually The Satanic Bible.”

Similarly, Miller’s character on Crashing likens comedy to a religion and comedians to modern-day preachers, something Real Pete believes “to a ridiculous extent.”

“As a culture, we used to gather around the fire, and then people gathered around Johnny Carson. Now we’re so displaced,” he said. “There’s so much entertainment that you can really find the perfect niche for you, but there’s no communal gathering place. A lot of people don’t go to church anymore. But you can go to a comedy club. If you do a comedy show and people are laughing at their fears and their shortcomings and all that, everybody blends into one thing. That can be strangely therapeutic, in a way that it’s not even on TV. I don’t want to say ‘sacred,’ but it’s verging on sacred.”

On a 2012 episode of You Made It Weird, Holmes’s interview podcast, he told guest Chelsea Peretti that he didn’t believe in the same God he once did. “But I do believe that there is something,” he added. “I absolutely do — I feel like people that lack belief have somehow lost the wonder of just this existence. This life. The fact that this exists is a miracle to me.”

YMIW draws high-profile personalities from the stand-up world and beyond — think Bill Burr, Zach Galifianakis, Jon Hamm, Deepak Chopra, Tig Notaro, Ben Folds, John Mulaney, Aziz Ansari, Aaron Rodgers, Henry Rollins, “Weird Al,” and the late Harris Wittels — into wide-ranging discussions of comedy, sex, and God. Holmes has called You Made It Weird his “filthy ministry.” The openness he’s demonstrated time and again in the recording studio is also evident in person, as when he nonchalantly traces his own origins as a comedian to an “overloving” mother and a “dad who’s not impressed.”

Holmes routinely asks his podcast guests about the time they laughed the hardest, and I wanted to know if he’d had any recent experiences that made his personal hall of fame. He described a moment he shared with his fiancée during a previous stay at the same hotel. After making a joke he was proud of, a stoned Pete — in his underwear, with his sweatpants pulled down to his knees — had thrown his hands into the air “with double peace fingers.” (He demonstrated the move for me, looking like Winston Churchill flashing two V-signs, minus the cigar and plus another eleven inches of height.) But the ceiling fan was on, and he stuck a hand right into it. “And then I tripped and fell on the bed, and Valerie laughed so hard she farted,” he said. “We called it the funniest nine seconds that’s ever happened.”

This made me think of one of my favorite of Pete’s stand-up bits, about the time his mother referred to her favorite singer, Céline Dion, as “Salon Dijon.” Holmes celebrates the serendipity of naturally occurring comedy gold like this in his 2013 special Nice Try, the Devil: “I honestly don’t know why we’re all not doing backflips right now. [‘Salon Dijon’] is a gift. I haven’t even added anything. It’s like a cat bringing a dead bird. It’s a treasure.”

As a comedian, Holmes told me, “what you’re actually selling is presence and awareness. It’s not taking reality for granted. That’s the name of the game for me, to always be in that place.”

Over the past several years, Holmes has joined forces with former pastor Rob Bell — author of books such as What We Talk About When We Talk About God and one of Time‘s 100 Most Influential People in 2011 — for live shows that bridge comedy and spirituality in onstage discussions. In an email, Bell — who’s also guested on You Made It Weird — called his improbable co-headliner a “genius.”

“Pete hasn’t lost the wonder,” Bell said. “We have more technology and luxury and information than anybody ever in the history of everything, and yet somewhere along the way to gaining all that, so many lost the sense of wonder and awe that we’re here on a ball of debris flying through space, breathing oxygen and walking our dogs. And then along comes Pete….He’s wrestling his demons like everyone else, and yet he’s filled with actual, real, genuine joy. And that’s intoxicating.”

With an apology for sounding “too Ram Dass–y,” Holmes explained, “If you can be in the moment fully, everything is very novel. Like, we’re always comparing this interview to another interview. Or this couch to another couch. But if you can really own the fact that this is the only thing that’s real, not only does everything become more vivid and important and vital, but things do become a lot funnier.”

I asked him about the kinds of moments he was trying to focus on in the remaining days before his show debuted on HBO. He admitted they were hard to pin down — just as he can’t fully remember the feeling he had when The Pete Holmes Show premiered on TBS. Holmes paraphrased a piece of wisdom he attributed to Bruce Springsteen: “You don’t remember your album going platinum. You remember a hot fudge sundae.”

“And that’s completely true,” Holmes said. “So when the show got picked up from pilot to series, Val and I went and got ice cream.

“Vegan ice cream,” he added. “It was still good.”