Crashing Crashing: On Set with Pete Holmes and Judd Apatow

The last time I visited the set of HBO’s Crashing, they were filming in recreations of New York comedy clubs within a giant Brooklyn soundstage. This time around, they’re filming in the real thing—the cramped, atmospheric, iconic Comedy Cellar in the heart of the West Village. The first thing that strikes you once on-location is just how accurate the recreations are. The various set dressers and art directors running around mean business regardless.

For Pete Holmes, who created Crashing and stars as a fictionalized version of himself exploring the New York comedy scene, filming here comes with its fair share of reverence. This is, after all, the club from Jerry Seinfeld’s documentary Comedian, whose depiction of the world of stand-up changed Holmes’ life. “Those stairs were, and kind of still are, intimidating to me,” says Holmes, gesturing to the back hallways of the club where performers enter. “So I don’t feel like I’ve won or killed the beast or anything. But I do have a lot of moments of gratitude, especially as we’re recreating these scenes that happened in the Cellar in real life.”

For two seasons, Crashing has been revisiting elements of Holmes personal life—namely, his divorce—as a way of charting his development as a performer. Not bad for a pitch that Holmes originally gave to executive producer Judd Apatow as part of a sketch on his TBS talk show, The Pete Holmes Show. “One of the things he pitched was his life story,” says Apatow, taking a quick breather from the director’s chair he’s occupying for this episode. “And I told him that it was too sad. In the sketch. I said ‘that’s way too sad.’ Later he came back and really pitched it, but it was the same idea. And then I thought, ‘sounds like it could be funny.’ And that was Crashing.”

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Madeline Wise, Pete Holmes, Judd Apatow

In the cellar of the Cellar, crew members, extras and actors are packed together, forming a makeshift holding room. A rolling barricade of monitors faces the show’s writers and writers’ assistants and gives them several perspectives on the filming going on upstairs. They are flushed against a back corner, not unlike the more established comedians who will be featured at a mobster-esque booth upstairs during the episode. While the script is basically locked at this point, they’re still hard at work punching up moments and suggesting alternate jokes for certain scenes. The episode being filmed now revolves around Pete bringing his new girlfriend (Madeline Wise) to a screening of his ex-girlfriend’s (Jamie Lee, also a writer on the show in addition to being Holmes’ real-life ex) TV appearance, where she is upstaged by the unexpected arrival of the “godfather of alt-comedy,” Emo Philips.

Emo himself can be seen slinking through the crowd, costumed in (or maybe just wearing) a vest and kind of mid-length tailed coat. “He’s like a Hogwarts professor,” says one writer. “Master of the Whimsical Arts,” says another. Flexing these particular muscles proves worth it, as jokes on Philips’s appearance will shortly be flung rapidly at the actors as they marvel at him within the scene.

The world of the Cellar is an interesting one to capture, especially as Crashing necessarily has to map Holmes’s past experiences onto a contemporary comedy scene that has changed rapidly in the last ten years. “Comedy used to be a little bit harsher,” says Holmes. “Now I sound like an old person. I’m sure it’s still very harsh. It’s still very scary… Alternative comedy was a response to too many hacks—too many people going up and doing the same premises, selling it with energy but no substance… If we’re turning the volume up on anything, it’s the harshness. Because it’s not as harsh as it used to be.”

Pete learning to navigate that harshness as he breaks out of his formerly-born-again shell is the backbone of Crashing, and an important angle for TV writing as Apatow is concerned—one that he learned from his late mentor Garry Shandling. “You have to write these as dramas, and then if the drama works, it’s much easier to make them funny,” he says. “That’s what Garry would say: ‘what would happen? What would really happen? Not for TV, but what would you say if you’re in that moment?’”

Wayne Federman, Colin Quinn, Judd Apatow

Apatow is particularly hands-on in making sure that Crashing holds itself to this standard, Holmes says. Especially today, for even though Judd cannot be seen on the monitors, his voice booms through everyone’s headset as he directs, giving Holmes and the other actors variations on every other line, blitzing through them as fast as possible so they’ll have options in the editing room. Later, when the action shifts over to the notorious comedians’ table, where Colin Quinn and a few others riff on Emo’s sudden reappearance at the club, Apatow throws away the script entirely, electing to just record Quinn’s genuine memories of Philips, as would likely happen, according to the Shandling rule.

“If Emo Philips walked in,” says Apatow. “Colin would say ‘last time I saw that guy,’ and he’d have some story. And that would get the ball rolling. We didn’t plan any of those jokes about Emo, but I knew if they just talked about the last time they saw him… it would also lead to them making fun of each other. There are certain moments when I give up on writing it. I just say, ‘well, have the Emo talk!’”

As they pull the third season together, Apatow and Holmes have their eyes on new possibilities for Pete’s character, having already taken him far from his origin as a sad sack crashing on the couches of his more successful friends, and further into the casual confidence that defines Holmes’s current day stage persona. “It’s a season where Pete gets funny,” says Apatow. “We can finally try to write good jokes for him, which has its own challenges.” Both separately acknowledge the influence of Extras’ second season, which depressingly dives into what happens after you get what you think you want. Despite his current stability and seeming upward mobility as a comedian, Pete’s troubles will be far from over this season. “He has an ego now,” says Holmes, “and that’s always going to get you in more trouble.”

Crashing’s third season premieres on HBO in 2019.

Graham Techler is a New York-based writer and comedian. You’d be doing him a real solid by following him on Twitter @grahamtechler or on Instagram @obvious_new_yorker. A real solid.