The Tao of Pete Holmes: HBO’s ‘Crashing’ Creator on Comedy, Sex and God

Pete Holmes on the spiritual journey that led him to create HBO’s new comedy Crashing.

Maarten de Boer/Getty

1. Comedy

When Jerry Seinfeld created his eponymous sitcom in the late 1980s, he cast himself as the successful stand-up comedian that he already was. Two decades later, Louis C.K. did the same on his show, Louie—his personal life may have been a disaster, but on stage at the Comedy Cellar he was confident and hilarious.

Now comes Crashing, the new series created by 37-year-old comedian and podcast host Pete Holmes, premiering this month on HBO. Like his predecessors, Holmes plays a version of himself on the show. But while he may be at the height of his stand-up powers in real life, on Crashing, he hasn’t quite found his voice yet.

“I bomb throughout the whole first season,” Holmes says. And that’s the point.

On a sunny afternoon this past November, Holmes and I meet at H Coffee House in the Los Feliz neighborhood of Los Angeles, not far from where he lives with his new fiancée. With his first big stand-up special—Faces and Sounds—about to premiere on HBO and Crashing right around the corner, he’s feeling a bit “overwhelmed.”

“Overwhelming sounds bad, but I think it can be a good overwhelmed,” he says, one of the many times during our conversation he stops to analyze his own choice of words. “It’s like a positive overwhelmed.”

The Pete Holmes who appears in Crashing is very different from the one viewers saw in his recent stand-up special. That’s because the Judd Apatow-produced show, which will follow Girls starting February 19th, finds Holmes back where he started in his comedy career over a decade ago. At 26 years old, he saw his four-year marriage implode and ended up “crashing” on various comedians’ couches in New York City.

“I think it’s really empowering to go back to the painful, early years of stand-up and relive them for other people’s entertainment,” Holmes says. “It’s kind of a way of taking ownership over those baby steps that every stand-up had to make, no matter how great they are now.” Even Louis C.K., he says, “stunk at the beginning.”

“That’s kind of an untold part of the journey,” he says. “Any time there’s a TV show about a stand-up, they’re typically very good. And that makes sense, because it’s very easy to sneak laughs into your show that way.”

Seinfeld and Louie would routinely cut away from the main story action so that their fictional selves can show off their best stand-up material, delivering some of the biggest laughs of any given episode. Crashing doesn’t have that luxury because Holmes, at least in this first season, just isn’t very funny yet.

“It’s certainly an art to try to make bad stand-up amusing,” Apatow tells me by phone a couple of weeks before the show’s premiere. During the scenes in comedy clubs, Apatow would have Holmes perform his older material four or five times in front of a crowd of extras until “they just start getting bored of it and then it feels like he’s bombing.”

“It’s a fun challenge to find the type of jokes that make the audience like him and want to go on this journey with him, hopefully towards success,” Apatow adds, even if they are not funny in a traditional sense.

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Holmes describes Crashing as an “origin story” of sorts. “Not like I’m some great, epic comedian, but the origin story of all of us,” he says. “It’s universal.” It also given him a chance to revisit some of the jokes he told when he was first starting out at open mics.

For instance, in the second episode he does a bit about the one racist guy who must have been upset that “Klan” is misspelled in Ku Klux Klan. “It’s KKC!” he imagines the man saying at the group’s first meeting, to a handful of polite chuckles from a drunk crowd in Albany. “Just a rare person who hates bad spelling and people who are different,” he adds before essentially apologizing to the audience for failing to make them laugh.

Preparing for the show, Holmes returned to real-life open mic nights to watch younger comedians work. “I’d always have this distinct feeling like, if I did my act here now, it might not do that well,” he admits. “Sometimes rooms are so bad that doing well isn’t an option.”

Holmes conceived the idea for Crashing after he found out his short-lived Conan O’Brien-produced late-night show on TBS had been canceled. “I knew I needed something new to do, so I took a quiet moment to think, what is it exactly I want to do? What’s the story I want to tell?” he recalls.

When he arrived at the idea for an autobiographical series, he immediately thought it would be a “perfect” project for Judd Apatow to produce. It helped that Apatow had done Holmes’ podcast You Made It Weird and appeared on The Pete Holmes Show, ironically in a sketch where the host pitched him movie ideas.

While Apatow was filming Trainwreck with Amy Schumer in New York, Holmes flew out from LA for one night to sell him on the idea for the show. During that shoot, Apatow had himself been mounting a return to stand-up comedy, performing in New York clubs like the Comedy Cellar at night.

“Judd started as a stand-up, he’s always maintained an intense and inimitable passion for stand-up. But it had just been rekindled,” Holmes explains, excitedly. “And then I come along exactly at that right moment and say, I want to do this show, which on the one hand is about heartbreak and starting over and renewal, but on the other hand is a really fun exploration of what it’s like to break into the stand-up world.”

The show was so in Apatow’s wheelhouse that he almost had no choice but to say yes.

“Comedians really are like a species,” Holmes says, highlighting the special bond he shares with Apatow. “That’s not to be exclusive. Anyone can kind of become one, you have to pay your dues though.” Holmes has been known to refer to non-comedians as “civilians” on his podcast, a distinction that could be viewed as derogatory, but which he insists is meant with no ill will.

In Crashing, after Holmes’ wife leaves him, he’s embraced by a series of fellow comedians who barely know him: Artie Lange in the pilot, then his real-life friend T.J. Miller, and most touchingly Sarah Silverman, who brings him into her home almost as if he’s a stray puppy.

Like The Larry Sanders Show, on which Apatow wrote near the beginning of his career, Crashing is about comedy and show business on its surface, but really it’s just about human behavior. “We’re not trying to break the reality with an unrealistic joke,” Holmes says.

One of those harsh realities is Holmes’ untenable financial situation. Without his wife to support his dream of becoming a comedian, he’s left on his own with no income and nowhere to live.

On most shows about stand-up comics, Holmes says, “You don’t need to explain why they have money or free time. It’s like, ‘Why is Jerry Seinfeld going to Vermont with that woman?’ Because he’s a comedian and he has free time, he can do whatever he wants. It’s perfect.” On Crashing, he wanted to explore the more difficult parts of becoming a comedian, including the humiliating experience of “barking,” or handing out fliers on the street in order to get stage time.

“When you start out as a comedian, you’re not good,” Apatow says. “So you’re trying to figure out how to make a living at something that you’re not good at. And it’s very hard to pay your bills. You realize that if you stick with it and you’re talented, you will get good, but you don’t know if it’s going to happen in six months or five years.”

“The whole system is somewhat abusive,” Apatow continues. “They force you to hand out fliers. Or if you want to perform, you have to buy two drinks. You have to bring people to the club. It’s almost created to get people to quit. It’s like when they force Navy SEALs to be under water too long to see how they handle it. That’s what being a young comedian is like.”

Nearly 12 years later, Holmes has officially broken through to the next level. “My life right now is pretty plateau, not in a bad way, but it’s not the same sort of knock down, drag out, I gotta eat, I need to find a place to stay, I need to get my shit together,” he says. But while that type of struggle may make for a more interesting television show, he doesn’t believe it makes for better stand-up.

Quoting his friend, comedian John Mulaney, Holmes says “pain gets in the way” of comedy. “The understanding that creativity comes from suffering is right and wrong at the same time,” he says. “I don’t need my life to be in shambles. It helps to get enough sleep, to not worry about food.”

His process has evolved to the point that he doesn’t stress too much about developing material, trusting that the jokes will “present themselves” to him when they are ready. On occasion, he will think of a bit in the middle of night and force himself to write it down. This reminds him of a classic joke by the late comedian Mitch Hedberg: “If I think of something funny, I have to write it down. Unless the pen is too far away. Then I have to convince myself that what I thought of wasn’t that funny.”

“And I’ve done that, I’ve fallen back to sleep going, that’s not that great,” Holmes says. “I don’t want to be too deliberate. There’s nothing funny about trying. And there’s nothing successful about not trying,” he adds, cracking himself up.

2. Sex

Like his character in Crashing, Holmes was a virgin before he got married at the age of 22. He jokes in the show that knew he would tie the knot with his now ex-wife the first time she gave him a blowjob.

For legal reasons, Holmes has to say that the show is only “loosely based” on his true story. “But yes, it is inspired by my life,” he says. The first person he called after he found out his wife had been cheating on him was fellow comedian Nick Kroll. They weren’t “super-duper close” at the time, but he knew that Kroll was connected to a lot of people in the New York comedy scene. And Holmes literally “needed” a place to stay.

T.J. Miller, who appears as himself in the show, was also a “really phenomenal” friend at the time, Holmes says. They knew each other a little bit from doing comedy in Chicago, but “the tragedy bonded us together so much more.”

In the show, comedian Lauren Lapkus plays Holmes’ wife Jess. Less than seven minutes into the pilot, he walks in on her after she has just finished sleeping with another man in their bed. On TV, that man is an overly-friendly bearded hippy named Leif, but as Holmes has repeatedly told his podcast listeners, in real life it was a small Italian man named Rocco.

“My marriage wasn’t bad. That’s what made it sad, is that I didn’t want to break up. So I don’t have any vindictiveness or ugliness for her,” Holmes says of his real ex-wife. “We haven’t talked since we split up, so it’s been almost 10 years, but I really do have love for her.”

When I ask if he thinks his ex-wife will watch Crashing, he struggles with the best way to answer. “I don’t care if she watches it or not,” he begins. “It might be easier for her to not watch it. I can’t make that call.”

“But if she did see it, I hope that she would be proud that we represented my wife on the show as a very, very sympathetic character, who wants to leave this person, but doesn’t know how,” Holmes continues. “That’s how I see my wife: someone who quite frankly was brave. She knew she wanted out. She got married when she was 24, I was 22. And she did the only thing she knew to do.”

The show is by no means “some sort of revenge piece,” Holmes insists. One of the “revelations” he remembers having about his real divorce is that “if there was a TV show about my wife, you would have been rooting for her. And it’s not because I was a drunk or I wasn’t around or wasn’t emotionally available, or any of the normal things.” It was simply, “I don’t think this is what I’m supposed to be doing,” he says. “Sometimes breakups are as undramatic as that. We loved each other. I think she probably still has love for me. I certainly have love for her. It just wasn’t what we were supposed to do.”

As “painful” as it was at the time to hear that she had fallen in love with someone else, now he thinks, “She did what she needed to do to live in her truth.”

At that point, he catches himself being cliché. “I know that sounds like somebody who, you give me three beers and I’ll start calling her a bitch or something, but that’s not the case,” he says. “And making the show was therapeutic in its own right. And I got to be married to Lauren Lapkus,” he says, pivoting into a joke. “And then she left me! What’s wrong with me?”

In the years since, Holmes has often extolled the virtues of polyamory on his podcast, questioning whether monogamy is possible or if he would ever get married again. But just this past month, Holmes got engaged to his longtime girlfriend Valerie, announcing the pending nuptials on his Instagram account.

During the intro to a recent podcast episode, he revealed that when he told his mother about the engagement, she responded by asking, “Oh, you’ve been living illegitimately?” He told listeners, “She was joking, but she didn’t burst into glitter as I was hoping.”

Like Marc Maron, who saw his comedy career take off after starting his refreshingly honest podcast WTF, Holmes has seen his profile rise considerably since he launched You Made It Weird in late 2011. For the first time he found himself performing for fans of his and not just fans of comedy in general. “You don’t have to say, ‘I’m from Boston, I got married when I was 22,’” he explains. “They already know who you are.”

But doesn’t he think it’s “weird” that so many people know so much about his personal life from the podcast? “No, what’s weird is that I don’t think it’s weird,” he replies. “It’s very liberating. I think a lot of pain in people’s lives comes from not being open and honest about what they really think, what they really feel, what they like, what they don’t like.”

“I like laying out the wares of my human experience, like a yard sale, and saying, here it all is!” he adds. It’s all “grist for the mill,” he likes to say, urging any up-and-coming comedians to “live a life worth commenting on.” Instead of starting from zero, this familiarity with his fans allows him to start at about a seven.

“If you start a show at zero, you might get to seven,” he says. “But if you start a show at seven, you’re going to go past 10, which is great.”

3. God

There’s a scene in the pilot for Crashing where Holmes is in his car listening to a CD of the televangelist Joel Osteen. Having just left his wife, the religious teachings don’t resonate in the same way they once did and he ejects the disc. Like so much else in the show, this spiritual evolution comes directly from his own experience.

After his divorce, Holmes says he would try to listen to Osteen, who he “really loved” at the time. “It just couldn’t find anywhere to land anymore,” he says. “When everything was going right, it made perfect sense. Then things went sideways.” The drift away from and back toward religion is part of the narrative Holmes hopes to explore in future seasons of Crashing, should he get the opportunity.

“Losing your faith is an essential part of having a three-dimensional, vivid, vibrant faith,” he says now, quoting Jesus as readily as he quoted Mitch Hedberg earlier in our conversation. “I think that’s what Jesus is talking about when he says, ‘Whoever wants to gain his life must lose it.’ These things that don’t make any sense unless you’re on mushrooms.” This leads him to title of the book Bilbo Baggins is writing in The Lord of the Rings trilogy: “There and Back Again.”

“I think it’s very significant that in any hero’s journey—you start in the Shire and then you come back,” he says. “But when you come back, you’re different. Everything’s where you left it, but you’ve changed. My spiritual journey definitely had me leave and it had me wounded and it had me scared. I’m back in a similar place, but it’s also completely different.”

Despite Holmes’ assertion that it was the combination of beginning stand-up and ending a relationship that made Crashing an ideal project for Apatow, it was actually this spiritual side that intrigued the super-producer right off the bat.

“I was really drawn to the fact that it was also about religion,” Apatow says, noting that spirituality had been on his mind lately as well. “The idea of a young, naive, religious comedian trying to navigate the dark waters of the New York comedy scene seemed like a great way to bring up all sort of issues for someone who’s trying to keep their soul while also trying to be a comedian.”

At the same time, it was Apatow who made sure Holmes never got too “preachy” on show. “We’re trying to make sure that his character is behaving in an organic way, so we have to pick our moments that his spirituality would reveal itself,” he says. “I just don’t want him babbling on and on without a joke or without serving the story or the character.”

Nowhere have Holmes’ spiritual explorations been more openly on display than in his extended podcast conversations with fellow comedians. In each episode, he strives to cover three distinct areas: Comedy, sex and God. The third subject on that list invariably comes last, when his guests are at their most vulnerable and open.

With more than 350 episodes to date of You Made It Weird, averaging around two hours each, if not more, dedicated fans—like this reporter—have listened to Holmes talk for upwards of 700 hours over the past five and a half years. With certain guests, like his friends Bo Burnham and Matt McCarthy, the conversations have stretched past the three-hour mark.

Holmes describes podcasts as the “wild west” of media today, which is why he doesn’t understand why so many limit themselves to only an hour.

“You can talk about almost anything. You can swear, you can be filthy, but you can also be majestic and glorious. You can really do whatever you want,” he says. “Why did we take a little piece of corporate America and say, it should be an hour? I understand aiming for an hour, but the idea of wrapping it up because you’ve hit a number on an arbitrary system of time—it’s like, OK, the Earth has gone this far around the Sun, we should stop.”

Time and its inherent constraints represented one of the biggest challenges for the talk show he hosted on TBS, which could run only about 22 minutes without commercials. “The talk show maybe would have been better expressed online, because those conversations where you’d see a five-minute interview, we’d talk for an hour at least,” he says.

Premiering in October 2013 after Conan, The Pete Holmes Show aired 80 episodes over the course of eight months before TBS abruptly canceled it in May of the following year, citing poor ratings. He now admits it just wasn’t the best format for him to express his comedy.

“There’s something about a podcast that feels like two people in a closet with the lights off,” he says. “As soon as you apply make-up, it’s over.” He’s had offers to film the podcast or have a photographer take photos, but he’s always said no. “I don’t even like having another guest in the room,” he says. To guests who want to bring a friend along, he tells them they can do whatever they want, “but you’re only hurting yourself, it won’t be as good.”

“We’re so hungry for something authentic, and that’s why going past an hour—lately I’ve been noticing when you go past two hours, there’s another break.” While some people can “keep their guard up” for two hours, he says it’s in that third hour that they go, “OK, let’s talk about my dad.”

He remembers doing an episode with Shannon O’Neill, who serves as the artistic director for the UCB Theater in New York, in which the first 45 minutes felt like a “pretty standard interview.” Then he “got lucky” by asking her about her husband. She told him she was actually getting a divorce.

“Of course, that’s horrible. But I was like, ah, I’m divorced! And now we’re in it,” he says. “The air changed. Literally, you felt a shift in the room and all of a sudden, eyes are glassier, everything’s still and we’re really there. And you just know you’re there. If it had been an hour-long podcast, at 40 minutes I would have been thinking of a way to wrap it up, not a way to crack it open.” They ended up talking for another hour and a half.

Holmes compares that experience to the time Alec Baldwin hosted David Letterman on his Here’s the Thing radio show on WNYC back in June of 2012. “Letterman seemed like he didn’t want to go. He was like, ‘Is that it? It seemed so fast,’” Holmes remembers. “Keep talking to David Letterman! You realize we all die and at some point this will be a record of David Letterman? If I talked to David Letterman, you bet your bippy it would end with him saying, ‘Jesus Christ, wrap it up, I have to go.’”

Shortly before comedian Garry Shandling passed away suddenly last year, he appeared as a guest on You Made It Weird. “Now I interview everyone like they’re Garry,” Holmes says. “Everything’s impermanent, and that was a lesson I learned from that. I might be tired. I might not have it in me, but you’ve got to push, because this is bigger than just my day. It could be the next person to go.”

“And we all go, so let’s not freak out. Everybody goes,” he continues. “But you’re talking to someone and you’re thinking this could be my one shot to get that beautiful story that could change people’s lives on the record.”

Holmes had a similar experience with his friend Harris Wittels, the Parks and Recreation writer who died of a drug overdose at the age of 30. Three months before his death, Wittels opened up to Holmes on the microphone about getting mugged while trying to buy heroin and his failed attempts to get clean. As “heavy” as their conversation was, Holmes says, “I think he would be glad to think that story could help people.”

Among the questions Holmes asks nearly every single one of his podcast guests are, “Dead over?”—as in, is there an afterlife or is it “lights out”?—and, “What’s the hardest time you’ve ever laughed—or, as his guest have corrected him more than once, “What’s the time you’ve laughed the hardest?” That dichotomy between existential dread and pure joy sums up Holmes’ comedy better than just about anything else.

One other piece of wisdom that Holmes has shared with listeners over the years concerns the benefits of imagining your life as a TV show. He likes to say that even when you are having a terrible day or something truly tragic is happening to you, all you have to do is think of it as a television plot and you will realize that experience would make a “great episode” of the show about you.

Now, Holmes gets to put that theory to practice in Crashing.

“That’s why we’re making it as a show,” he says of what was arguably the most difficult period in his life. “It was such a good episode that we’re making it a show.”