Production on season two of HBO’s Crashing just wrapped in New York City at the end of August, with plenty of on-location shoots at comedy clubs, sidewalks and restaurants, in addition to the studio they had to build to replicate the old Boston Comedy Club, which now itself is a restaurant on West 3rd Street.

The day before I caught up with Crashing‘s creator/star Pete Holmes and friends at Gotham Comedy Club (where they filmed an upcoming “Roast Battle” episode for season two), he had coincidentally been shooting just around the corner from The Comic’s Comic HQ in Astoria.

“We went to Lebanon. Have you been to that restaurant? You should go. It’s just called Lebanon. It’s impossible to Google,” Holmes told me.

He set Crashing in NYC because, in between starting his stand-up career in Chicago and moving to Hollywood, this really was where Holmes schlepped from comedy friend’s sofa to comedy friend’s sofa in the wake of his divorce, while also learning how to become the great comedian he is today. All while barking on street corners for the Boston and wishing he could get passed at the Comedy Cellar. Of course now, Holmes not only performs at the Cellar when he’s in NYC, but also gets to shut down the club to film his HBO series there, too.

“That’s actually one of the most absurd things — absurd in a good way — about writing these scripts, is you write,” Holmes told me during a break between filming in Gotham’s basement lounge. “I’m in my pajamas or sweatpants and I write, ‘INT. COMEDY CELLAR — EVENING’ because I’m trying to think of something that really happened, and it really happened at the Cellar. And our producer, Igor Srubshchik, is so good and the Cellar is so kind to us and to Judd and we’re all friends, that I show up on a Tuesday and they shut down MacDougal Street. That’s not an ego trip. That’s just an amazing experience to actually shoot something about the comics’ table and how it feels to try to hang out at the comics’ table when you’re an open micer, at the actual comics’ table. That makes a big difference!” “You know when you’re watching an old movie and they have fake search engines? WebLooker! And you’re like, now we’ve caught up and we use Google. Similarly if we were like, it’s a place like the Cellar but it’s not the Cellar, it takes you out of it.”

Although we’ll clearly see more scenes with Holmes and other comedians at Gotham and the Cellar when season two returns in 2018, the plots of Crashing also will explore the alt scene of bars and indie comedy rooms, too.

“The story in my real life was that I started at the Boston, so Boston Comedy Club was Season 1. In Season 2 I’m still at the Boston, but what happened in real life was, it was actually Demetri Martin and Jim Gaffigan. That sounds like name-dropping but that was 10 years ago, so Demetri Martin was big, Gaffigan was big, but anyway, why’d I mention that? So what happened was a guy like me who was very clean, very friendly, and going up at bars, clubs, you would follow very very funny guys but very very dirty guys, very very I don’t want to say clubby but just like heavy-hitting headliner guys that talked about life experiences that Pete, my character, me in real life, didn’t have. I was sweet. I loved Seinfeld. I loved Cosby. Obviously that’s a little complicated now. And I loved Brian Regan. So it was really about who I was going up after. It’d be an hour and a half of female ejaculate jokes — funny stuff — but you know, really brilliant guys like Patrice (Oneal) and all these guys, really killing. I’m not putting it down. And then I’d go up and try to, I had a joke about how I read something on the back of an ice pack. You know what I mean? So it’s really hard to get them even if it’s a decent joke, it’s hard to get their attention. Then Demetri came by the Boston and he went up and he actually didn’t do very well. I’d say that if he were here. It just wasn’t his crowd, and I was over the moon. I was just so happy that someone I admired and admire so much didn’t do well in the place I don’t do well. And that started making me consider something Gaffigan told me, which is you’re a product of your environment. The kind of comedians that you’re around are typically — if you go to the Cellar, a lot of the guys that have been there 15 years have a similar flavor. It’s a hilarious flavor, it’s a wonderful flavor that I love. And then you go to the alt rooms and there’s just a different spice on them. I don’t want to say it’s better or worse. 

But what happened in real life was Gaffigan and Demetri, and on Crashing we have a character that represents an amalgamation of those people in my real life, that see Pete, see that he’s like an observational sweetie, and says, I think you’d be better at 8 o’clock at the back of a video store. And that was true! The first time I went up at Rififi in real life, I told a joke that never worked, never worked at the Boston, and they laughed really hard. They might have even clapped, an applause break situation. And I was like, ‘What is going on here!?’ So that’s one of the transformations that we’re showing in Season 2.”

Holmes recognizes that the alt scene in 2017 doesn’t look nearly like what it did in 2007 or 2008, so they’ve necessarily exaggerated the look of these rooms for HBO.

The stories don’t need to be exaggerated, though. Fellow comedians Greg Fitzsimmons, Beth Sterling and Jamie Lee wrote and broke episode storylines with Holmes for season two of Crashing, and swapped plenty of tales about the odd and ugly experiences they went through on the road coming up. If Holmes has to remind himself of anything while filming Crashing now, it’s that he has to remember not having the same level of joke-telling skills when going back in time to his younger self for filming.

Holmes and recurring guest star Artie Lange reminisced with me about the trick in doing just that, and revisiting some of their jokes from a decade ago, in a special episode of my exclusive Laughly series, On Second Thought.

Holmes did find himself having to remind the other comedians not to pay so much attention to him in scenes, too — he may be the star of Crashing, but he’s not supposed to be a star in the realm of the show. “I often have to say, be meaner, be more dismissive,” he said.

The other big difference in filming season two is the freedom that comes with dispensing of the storylines from season one, which revolved mainly around the dissolution of his marriage.

“In one way it was a little bit easier, because everything was so rooted in some conversation or inspired, I should say, by some conversation or feeling I had about my divorce. That was very loaded and it helped me get into my scenes,” Holmes told me. “But, a lot of times, it’s kind of like being a comedian yourself. For the first 10 years, nobody knows you, so all of your comedy is introducing who you are. Hi, I’m Pete and I’m from Boston. I’m friendly. I’m tall. I’m soft. All these different things. But once you build a fan base, you can write a different kind of act. You don’t have to say, ‘Hi, I’m Pete.’ In fact, that would be stupid. They’re like, we know. And you don’t have to say I was divorced, because they know. Similar with the second season, Crashing is almost like being a bit more of an established comedian in that in the beginning you can just pick up, you don’t have to say Pete’s still kind of feeling bad about his divorce, because you saw the first season. Even if you don’t see the first season, it opens and it’s very clear that this is a guy who just went through a breakup and is trying to find his feet. But I look at season 1 as kind of like Pete in denial about what’s happening, and season 2 as Pete accepting…”

Season one of Crashing is available now for rent or sale. Season two returns in 2018 on HBO.


Above: Pete Holmes at Gotham Comedy Club on the set of Crashing, season two, by Craig Blankenhorn for HBO