Inside 'Crashing': How Pete Holmes Survived Comedy and Lived to Tell About It

Amiable stand-up comic stages his own semi-autobiographical 'Seinfeld' on HBO, complete with early-years humiliations and Judd Apatow's help

Inside 'Crashing': How Pete Holmes survived his early years in stand-up comedy and made an HBO show about it, with a little help from Judd Apatow. Credit: Mary Cybulski/HBO

"Should I say, 'Fuck Philly?'"

It's backstage on the New York leg of Pete Homles’ stand-up tour to help promote his new HBO series Crashing, and he's testing a stray thought before stepping onstage. The green room is full of bodies – including Holmes' manager, his fianceé, the show's executive producer (and tour mate) Judd Apatow and several more HBO staffers – and there's a general murmur of assent. "They love that here," someone says, and the comedian nods. Their recent Philadelphia stop reportedly had a rowdy, disruptive crowd, and as Holmes explains later, you get used to knocking cities you're not in. "When you're in Boston, you say 'Fuck New York,'" he declares matter-of-factly.

But once he's onstage, Holmes doesn't damn the City of Brotherly Love outright. He grouses about the bros crying "show me your tits," and he confirms that the Gramercy Theater is getting a superior show, with better improvised riffs. But he never uses the phrase "fuck Philly." Not once. Maybe the 37-year-old stand-up really is as nice as his perky persona; maybe such a puerile hit job doesn't suit the mood. Or maybe, just maybe, Holmes is like his Crashing alter ego: A man trying his best follow the better angels of his nature in an attempt to save his soul somewhere down the road.

The show, which debuts Sunday, February 19th, revolves around a fledgling stand-up comedian named Pete who loses his wife, his house and every other signifier of a stable life after discovering his spouse in bed with another man. Shaken and demoralized, he exiles himself to New York City to focus on his craft in the open-mic comedy scene. Playing loose versions of themselves, stand-ups Artie Lange, T.J. Miller and Sarah Silverman show this cheery, somewhat guileless fellow the ropes, disabusing his fears about drugs, sex and every other aspect of the cruel new world he's entered. Pete begins to see the light on the horizon – often literally, at the break of dawn, given that he's surfing from one compatriots’ couch to the next.

It's a world Holmes knows well. He's been performing stand-up since he was 22 years old, working a persona that fit a 6'6" devout Christian with a long, rubbery face, a toothy grin and bits about toying with telemarketers or losing his mind at an Enrique Iglesias concert. He eventually started getting enough high-profile gigs to attract the attention of TBS, who gave him a late-night series titled, simply enough, The Pete Holmes Show. After it had been canceled in 2014, and having found himself with no job on the horizon, Holmes recalls asking himself a question: "What is the one story you can tell better than anybody?" The answer: his own biography. "I can tell the story of a religious guy who married the first girl he dated, and she left him, and then he started taking comedy a lot more seriously," he says.

The concept of mining his own background for material won't come as a surprise to Holmes' fans and listeners of You Made It Weird – his popular podcast in which doing bits with his comic buddies often segues into deep conversations about his personal history, God and the universe. Longtime devotees of YMIW, a.k.a. "Weirdos," know a lot about him, from the painful details of his divorce or exactly how many pumps he lasted when he lost his virginity. Asked whether fans would want to hear his story transposed to another medium, Holmes says, “I think about that all the time, because you know who's the first to get tired of it? Me. There are certainly days when I wake up and think, 'This again?' But the biggest fan of my podcast won't know where the story is going – because we just took an essence and built a world on it."

As to why the world needed another episodic show about comedians, Holmes mentions that shows like Seinfeld and Louie only provide the latter-day successes of comics, not their early days of struggle. "I don't think people know about handing out fliers [to get stage time at a club]," he adds. "Or doing audience warm up [for TV shows], or all of the odd jobs we have to do to scrap together a living for a decade,. Crashing is the highlights of what it's like to start in comedy – if you take out all the good times and laughing and sleeping and eating to comfort yourself."

Once Holmes had worked out Crashing's basic semi-autobiographical premise, he realized the story of a sad-sack underdog battling an upward climb of open-mic nights and bombing at 2am slots sounded a lot like ... a Judd Apatow vehicle. "I happened to pitch the show to Judd at a time he was getting back into stand-up himself," he says, "He's sitting at those tables with the comics, he's staying up 'til two in the morning doing spots – and then I pitch him a show about the quiet romance of the comedy scene." Intrigued, the Girls' producer walked Holmes into HBO and gave the network the hard sell. "If the stories are built right, comedy isn't the difficult part,” says Apatow. "If Pete's asking somebody if he can sleep on their couch because he has no money, it's inherently dramatic and sad – but also really funny because it's so awkward."

For Apatow, the show is really about "a religious person interacting with the wonderful and sometimes wounded people who inhabit the comedy world." The producer advocated for famed Howard Stern affiliate Artie Lange to play Pete's comic sherpa ("He's really open about his struggles and where they stem from," Apatow claims). The effect of pairing a goody two-shoes with a grizzled veteran dragging around the weight of a dark past lends a yin-yang dynamic to the Odd Couple pairing. "Pete is religious, he has never slept with anybody, he's never done a drug – this was all based on my real life at that point," Holmes admits "Then he meets somebody who's like five comedians rolled into one." There's a pause. "That's not a fat joke. Artie really represents a lot of guys with that East Coast working-class, leather-jacket, Yankee-hat vibe."

Plus, both Holmes and Lange are comedians that have survived what Apatow calls the severe vetting process of stand-up – and both have persevered not because they want to make strangers laugh in a dark room with a two-drink minimum but because they have to do it. "The people who do it are insecure," he says. "But they want to succeed so badly they force themselves to suffer through this early, painful stage. And that's what makes these people so interesting. They love it so much that they are willing to be humiliated to figure out how to do it."

It's one thing to have suffered through the slings and arrows of outrageous fortune (and drunk hecklers) when you're making your bones in comedy clubs; it's another thing entirely, however, to relive those difficult parts of his past in front of a large cast and crew. "I said to Lauren Lapkus, who plays my wife, 'This is like cramming six years of therapy into an afternoon,'" he says, before comparing the experience of acting alongside actors pretending to be his parents to being "in an episode of Black Mirror." Even so, he confesses that the most difficult parts of the shoot were the recreations of bombing in front of audiences in comedy clubs; Apatow would just roll the camera while the comedians did their actual material over and over. “Let me tell you, you can authentically evoke the feeling of dry mouth and lower back sweat," Holmes admits. "Your lizard brain doesn't understand, 'This is just for fun.' You feel like, Oh man, you're letting these people down. I had a new appreciation for past me, and for people who are starting comedy now. It really is a pretty exciting adventure, but there is a lot of suffering."

Thankfully, Holmes now has the leisure to revisit some of those awful moments from a distance, in fictional form. Coming offstage at the Gramercy, Holmes seems entirely in his element. He does a brief interviews with Lange for HBO's digital team, signs posters for fans at a meet-and-greet and lets loose his signature bray whenever something strikes him as remotely funny. He's moved past the obstacles and insecurities with which his Crashing character struggles, he says – and he did it all without saying, "Fuck Philly." Maybe there's a chance for his soul yet.