Crashing Season 3: In the Comedy Cellar with Pete Holmes and Judd Apatow

The rain is just starting to come down outside as I disappear behind the big black tarp leading into The Comedy Cellar. The club is in the middle of shooting the sixth episode of Crashing Season 3. Judd Apatow, who serves as executive producer, is being called to the set. In the corner of the room the resident comics are seated at the comics’ table, they’d be there whether or not filming was going on. They’re always there. 

Apatow lets Pete Holmes, Lauren Lapkus, Jamie Lee and other members of the cast run through the scene, as the camera rolls you can here Apatow calling out lines from the sidelines awhile everyone on crew tries to muffle their laughter on the quiet set. At the moment Apatow is trying to nail a description for Emo Phillips who walked through the club. The characters on the show are as just as much in awe as everyone else in the room. “He looks like he floated in on an umbrella,” “he’s both emotional and business-like at the same time…” they run through about ten until Apatow is satisfied enough to re-block and try it through again. 

You can tell right away that Apatow is just happy to be at The Cellar. When he comes to take a seat with me he doesn’t look tense or tired as you’d imagine after filming nonstop for a few days, instead he looks like he’s just been sitting at the bar knocking back a beer with some pals. 

New York’s most iconic comedy club is closed for the week, which rarely ever happens. Instead, it’s been taken over by HBO’s Crashing to film for the upcoming third season.The legendary room is filled with cast and crew and barely resembles the legendary room comics from all over the country aim to perform in. In fact, you almost couldn’t tell where you are if not for the stained glass sign that hangs on the wall behind the mic, “Comedy Cellar.”

I’m watching a scene take place at the bar upstairs and Greg Fitzsimmons, a comic who’s also a writes on Crashing, is sitting to my left, Roast Battle winner Mike Lawrence next to him. Wayne Federman (Step Brothers, 40-Year-Old Virgin, Legally Blonde) is standing across from me. Even Emo Phillips is in the room. Sporting his usually mushroom cut, Phillips appears in the sixth episode of the season, the one they’re currently filming, and everyone in the room is laser focused on everything he’s doing. He’s rarely ever spotted  (a premise they’re using for the episode), but there he is in the Cellar on set. Judd Apatow, who serves as executive producer on the show, is directing this episode and as Pete Holmes, Lauren Lapkus, Jamie Lee and other members of the cast wait on their marks, Apatow’s calling out lines from behind the camera while everyone watching tries their best not to laugh.

A lot of a New York comic’s life takes place right in the Cellar. There’s no better tell to the movement of the show than being on the set of season 3. The Cellar was always a place that sort of alluded Pete. The comics’ table was in many ways forbidden fruit for Pete. It’s something that’s earned and that has proved intimidating to many comics, and if New York is a main character in the series, that so is the comics’ table. Maybe it’s even the antagonist.It’s the perfect spot for a show about a comic rowing through stages of his career.

Even though the show is about Holmes’ journey, the Cellar is really significant to Apatow as well. Apatow says that the first time he did stand up again after a 20-year hiatus was while filming Trainwreck. He decided to do a set at the Cellar just to “amuse Amy [Schumer]” but everyone was so nice that it made him want to give the stage another go and came back every night. 

“That’s definitely why I started doing stand-up again is because this club is so perfect,” says Apatow. “It’s packed almost every single show, every night of the week. The crowds are really great, educated, comedy crowds, so it’s the most supportive atmosphere you could possibly be in, and the lineups are the best people in the country. They’re ridiculous. And it’s very well run and they respect the comedians. A lot of clubs don’t care if the comedians are feeling supported. That would be the nice way to say it. But here they care about the experience for the comedians as well. So I think that’s what inspired me to not just do it as a lark, but to keep trying to develop my own act.”

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While the Cellar might feel comfortable at certain points in your career, to Holmes it’s still pretty daunting.  

“We were shooting and I looked up at the stairs, the stairs you come down to go on stage. Those stairs were, and kind of still remain, intimidating to me,” says Holmes talking about the narrow staircase leading from the Olive Tree down to the Cellar. “It was just so hard to get in. It’s analogous to what it felt like getting into comedy was getting into the Cellar.”

That feeling seeps through the entire show and though comics tend to move around a bit, Apatow and Holmes can’t make the jump just yet. When we last left Holmes’s character in season 2, he had just started the first leg of his college tour. After he beat out roasting Tony Hinchcliffe and, for lack of a nicer word, eviscerated his girlfriend Ali, played by Jamie Lee, Holmes packed up his bags, found his walling legs, and started “making it.” While the season two’s  “NACA” episode kicked off the college portion of Holmes’s career in the series, it’s not something that I, and presumably viewers, would like a whole season of. 

further reading: Crashing Season 2: Jamie Lee On Going From Writer to Co-Star

New York is as much a character in Crashing as is the parade of recognizable comedians and Pete himself, so to take that away from the show would feel uneasy. Holmes and Apatow thankfully whole-heartedly agree. “Judd and I both live New York and love the story of New York comedy,” Holmes says as we’re seated across a folding table in some office space next to the Cellar. “The one little foci point we have is New York Comedy. So moving the show from New York now, I don’t think would be a good idea.”  

Holmes explains that instead of watching his character jump from college to college, which isn’t so interesting to Holmes or Apatow, season 3 will jump forward a bit and bring Pete right back to New York after he’s wrapped up the tour and now has a bit of a chip on his shoulder. “[Pete’s], I don’t want to say he’s a jerk,” Holmes searches for the word, “but he’s a little more cocky.”

While Crashing is about a regular guy who’s trying to make it in comedy despite not checking the stereotypical boxes that we so often associate with comics. Pete is a nice guy whose demeanor of being courteous, polite, and straight edge mirrors growing up as a devout Christian. He’s only ever slept with one woman when the show begins, he barely drinks, he tells jokes about hailing cabs or being the “fun dad,” he’s the atypical comic. “He’s somebody who grew up being taught a certain belief system and lifestyle,” Apatow explains. “Now he’s deciding if that’s something he wants in his life or not.”

Because of his background, the first two seasons were very much about Holmes not only crashing on people’s couches, but crashing into obstacles most of which have to do with him not quite finding his niche in the comedy world —  something that began changing in season two and will be more apparent in season three. “This is a fun season for us because it’s the season where Pete gets funny,” says Apatow. 

Pete adds, “It’s not that Pete, my character, is going to get dirty —  although he might, or crasser, he’s just gonna be more honest. The comedians I see, especially these days, that grow and succeed, are the ones that figure out what’s in their corners. Seinfeld is my favorite, in Jerry Seinfeld’s corner, I believe is an observation about cotton balls. I don’t think he’s keeping too much of the goods away from us, but Pete, I think, is. In fact, that was my experience so I can say yes, he is.”

Pete has to get funny and has to succeed a little. A show can’t withstand more than a season or two if there’s no growth, but in a world where Holmes’s character is actually funny and has seen tiny glimmers of success, I had to know if the days of standing on street corners for stage time was over.

“The barking is done,” Holmes laughs. Going into the third season, a series obviously has to grow, but in a show about a comic “crashing,” how does Pete getting funny affect the premise of the show? “That’s the great thing about stand up, there’s never ending failure,” Holmes says at one point. “There’s a lot of ways to fuck up. Even though my character isn’t literally crashing on couches anymore, he continues to crash, because that’s what you do.”

“I think every year of a comedian’s life and career is interesting,” Apatow says. “Being bad’s interesting, figuring it out, getting good, getting paid, succeeding, losing your audience, getting them back, the heights of fame. I find it all fascinating. “

Crashing is the story of Holmes years ago, but despite how far he is in his career, he doesn’t feel like he’s slayed “the beast,” but just feels thankful and recognizes what the club meant to his career. 

“I don’t have a lot of moments like ‘simply the best,’” Holmes sings. “But I do have unending gratitude. This is a club where I perform and still feel reverence, because this is the club from Comedian, which changed my life, and there’s Colin [Quinn], and he’s in that movie and it’s freaking me out a little bit… it’s very surreal. It’s like Black Mirror if it was wonderful.”

What more perfect setting could there be for a show about constantly crashing up against imperfection?

Daniella Bondar is freelance contributor. Find more words on her author page and follow her awkward exchanges on Twitter @daniellarobin.