Why HBO’s ‘Crashing’ is TV’s Most Honest New Sitcom

Here’s a pitch for you: a naïve and unsuccessful performer discovers his wife is cheating on him, loses his marriage and his home, and winds up sleeping on various strangers’ couches while bombing hard night after night onstage.

Yeesh. Sounds like a real Revolutionary Road-style bummer, right? Somehow, though, that’s the basic plot of Crashing, the brilliant — and, yes, very funny — new sitcom from comedian Pete Holmes, which premiered last Sunday on HBO. “A lot of people don’t understand how it’s the set up for a comedy,” Holmes, who based the show on the actual events of his life, tells me with a laugh. “My parents, especially.”

One person who did understand? Reigning comedic overlord Judd Apatow, who executive produced Crashing. “The interesting thing about Pete is that he’s very positive,” Apatow says. “So much of comedy is negative, it’s cynical, there’s a lot of complaining — and that’s what’s great about it. So it’s rare to find someone who can be hilarious while trying to be a good person.”

That contradiction has become Holmes’ signature. His stand-up is mostly goofy — his latest HBO special, Faces and Sounds, is highlighted by a joke that wonders why unicorns aren’t called “unihorns.” His popular podcast, You Made It Weird, veers from gut-busting silliness to deeply existential pondering and back again on a dime. And his late, great TBS talk show, The Pete Holmes Show, similarly ran sketches about the X-Men getting fired alongside mostly-serious chats with people like Deepak Chopra.

Now he’s arrived at Crashing, a show that’s as much an anomaly as he is. Unlike other prestige-y, first-person sitcoms about stand-ups — Louie, Maron, et al — it gives an honest look at what it’s like to really struggle as an untested comedian and explores the raw emotions of a recent divorce, all while remaining sweet-natured, affecting and hysterical.

Here, Holmes opens up about what it was like to revisit the most difficult period of his life, his relationship with Apatow, and what makes him laugh the hardest.

SHARP: I’ve listened to dozens and dozens of hours of your podcast on my commute to work, so it feels like I know you a little already. And Crashing is based directly on your real life and the aftermath of your divorce. Is there ever a point where you think to yourself, “Have I shared too much?” Do you ever feel overly exposed?

PETE HOLMES: Well, the podcast comes out on Wednesdays, so usually every Tuesday around 5 in the morning, I’ll wake up and panic. [Laughs.] But, truth be told, I’ve kind of gotten over it.

The podcast started as an experiment: how much can you admit and not have people turn on you? And I’m happy to say it’s been a successful experiment. We’ve been able to say things that might have been ill informed or silly or, to your point, overly personal or vulnerable, and the response has only been good, which I’m happy to say.

It’s a little bit different with Crashing, because we’ve fictionalized it to such an extent that it doesn’t feel quite as vulnerable as speaking about my actual divorce. But, overall, I think I’m numb to it. It’s like kids that play too many video games — I’m numb to over-sharing.

So there wasn’t any hesitation on your part to revisit that time in your life, because the show doesn’t bear that much resemblance to what actually happened?

Well, it does emotionally. Certainly we changed the narrative, and the character of my wife and the situation are different [from what actually happened]. But one of the reasons I hope that Crashing will be something that people want to watch is because it has that authenticity, that honesty.

There is something true emotionally in every episode, for sure. With so many things vying for your attention in television, I think that’s kind of the new premium: it has to be truly heartfelt. And that’s something we were able to do.

The breakup scenes in the pilot are a good example: there was never anything like that in real life, but it’s still dancing around the feelings of what it’s like when somebody leaves you. So that was difficult. In the fourth episode, we recreated what it was like to tell my parents about [the divorce] — and that, again, was emotionally real. And then we had to do stuff where I was starting out as a comedian — being an open mic-er and bombing in front of a roomful of people. And of all those three things, I think not doing well as a comedian was the most painful.

[Laughs.] Yeah, I can imagine. Those onstage scenes are pretty hard to watch.

It wasn’t easy. The whole show wasn’t easy for a number of reasons, and one of those reasons is certainly because it reminded me so much of what it felt like at that time in my life. But, I kind of took that as a sign that we were doing it correctly. If we were ever just kind of coasting through, I’d go, “Oh, this isn’t what it felt like. I’m not doing the story justice.”

What was interesting to me — having come to know you through your podcast, your stand-up and your old talk show — is that outward silliness seems like such an inherent part of your personality. But the Pete on Crashing isn’t silly at all: he’s reserved, uncertain, and oftentimes quiet. Was it tough to tone yourself down and not let that sillier side loose?

We actually did [let it loose]. We filmed every scene three completely different ways: we’d do it as a straight drama, then we’d do it with some jokes, and then we’d do it again with lots and lots of silly jokes. That’s how Judd likes to work. But when we were editing the show, we really chose to avoid a lot of the more obvious jokes, because we never wanted to betray the honesty and the realness of the scene just to get a laugh.

It also gives my character somewhere to go. We’re really trying to be true to who I basically was when I was 28. And the truth is, if you listen to the early podcasts, I hadn’t quite figured myself out as much. So we’re leaving some room to grow. As we’ve started talking about Season 2, for example, we’re thinking about it in terms of how much better at stand-up Pete gets, how much more comfortable in his skin he is, all that sort of stuff.

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That makes sense. I did notice that while the Pete character is more restrained, there are places in the show where you’re able to insert flashes your current self in. There’s a point in the pilot where a character tells Pete, “I am you, I’m not your enemy.” It all sounded very Ram Dass [Holmes’ favourite spiritual author] and it felt, in some sense, like your present voice speaking to your past self.  

That’s exactly it. I’m glad you picked that up. Leif, the character you’re referring to, is kind of a hippy — he’s not really like me, but he’s a good mouthpiece for a lot of the things I now wish I could say to myself when I was going through my divorce. I like finding those little ways — it’s a weird game to play, to write a show about a regressed version of yourself and then try to dramatize and give a narrative to how you started to find yourself. We’re reverse engineering it.

You grew up a very religious person, and there have been a few hints at that in Crashing, as well. Is religion something you’d like to explore more of in the show going forward?

Yeah, you know, I look at the show as three major transitions. One is Pete getting divorced — that’s the first break up. The second break up we explore is between me and my family, where I start to put up some boundaries. And then the third one is not quite a break up [with religion], per se, but it’s similar — it’s Pete breaking up with his old understanding of God. And I’m very excited to continue that process.

[In the writers’ room] we always ask: “What could happen next?” And I always try to look at it through the lens of where Pete is with his faith. I think that — and I know Judd feels the same way — that’s what makes the show unique: it’s not just some guy coming up in the New York comedy scene, it’s a guy who’s really trying to cling to who he is. He’s trying to cling to the sweet boy that he is. There’s all this temptation around him and it’s going to be fun to see how he navigates that while reconciling it to his understanding of God.

You just finished explaining how the show is more than just about the comedy scene, but stand-up still plays a major role, and there are sides to it — like barking [handing out flyers for comedy clubs on the street]  — that have never been explored on TV before. Were you ever worried that those details might make the show feel too inside baseball?

That’s a fair point. It didn’t concern me because I feel like no matter what your dream is — whether that’s a job or some personal fulfillment you’re looking for — you can project yourself onto a comedian pretty easily. It’s somebody with thoughts who shares them. No matter what you do, you probably have thoughts and you probably share them. So even if you don’t have an interest in stand-up — and if you do, you’ll certainly get some extra juice out of this show — it’s an easy hero’s journey to follow and be like, “This guy wants to be heard. He wants to be accepted. He wants to be his authentic self.” I think non-comedy people will still see themselves in it for sure.

So I wanted to talk a little bit about the conceit, for lack of a better term, of Crashing. Every episode features a major guest star: in the pilot, you “crash” with Artie Lang, and in the second episode you wind up staying with TJ Miller. How did that concept come about, and was there ever a concern about structuring the show so heavily around guest stars?  

There’s a funny story. I remember calling Mike Birbiglia, who is a consulting producer on the show and a huge friend of mine, to tell him about this idea I had. I expressed exactly what you were saying. The reason most shows have a core group of four or five characters is because you can lock these people in contractually, scheduling is easier, and you can just bang out episodes faster.

So I told Mike, “I love this idea, but I don’t know if it’s practical, and I don’t know if the producers are going to like it.” And Mike goes, “Petey, are we really on this Earth to make an easy production schedule? Is that what we’re here to do?” [Laughs.] I laughed so hard. I was like, “That’s exactly it.” There’s the easy way, but we decided to go with the best way of telling our story.

The conceit of it, too, came about because in real life the first person I called after my wife left me was Nick Kroll. He’s one of these guys who knows everything and everybody, so I asked him for help finding a place to stay. John Mulaney helped me out, too. And then I wound up spending a week in Pittsburgh with TJ Miller, just hanging out while he filmed a movie. So it’s based on a real thing, this group of misfits — a lot of comedians are a little bit debaucherous, they’re heavy drinkers or they do drugs or they see prostitutes — and finding that grace and love and support in an unlikely place. It’s a story I always love to tell, and it’s exactly what happened.

In the end, it wasn’t that hard. We came from the talk show world where everything was contingent on guests, so we knew what to expect. And I’m so happy to say that we didn’t hit any road blocks: we got everybody we wanted to and everything went off without a hitch.

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How much did the experience of doing both your talk show and You Made It Weird influence how you approached Crashing? Were there lessons from either that you applied to this new show? 

Oh, for sure. From the talk show, I learned that you need to figure out what you’re getting at and get to it very quickly. And through the podcast, I got used to a new level of honesty, and that became my new normal. Most people I know who have been heckled or left by their partners or cheated on don’t exactly want to put it on television. But the podcast taught me that if it’s honest and true and it has a good purity to it, people will consume and understand it.

That honesty feels more potent than ever in our current political climate.

Yes, it definitely does. That’s exactly right.

Let’s talk about your relationship with Judd. You’ve referred to him in interviews as something of a father figure. What was that working relationship like, and what were some of the main contributions Judd made to the show overall?

A lot of people don’t understand just how important an executive producer is. I grew up thinking that just meant they paid for it: Oh, he’s the producer! He smokes a cigar and gives you money. But the truth is that I feel more like the ingredients, and Judd is the chef.

He’s credited as a writer on three or four episodes, but his name could have been on every single episode. I really love writing — I’m a fast writer, and I think I’m a good writer. But Judd is good at the part I’m not good at: he knows how to make sure that the story has stakes and is emotionally honest, and he pulls me away from anything too silly or stupid or inauthentic. Every episode, we’d sit down and talk about what should happen, and then he’d set me loose to write it.

So Judd really is my comedy father figure, and he’s just the best one you can hope for. He’s really available. He’s working on a movie and like three TV shows, and the fact that we could still call him from set, and he would come and direct, was amazing.

I wanted to finish up by running through a You Made It Weird-style speed round with you. What’s the most important lesson you’ve learned about showrunning?

Oh gosh. [Laughs.] Keep your mouth shut until you know every angle. Wanting to be a people pleaser is not the best way to be a boss. There’s a reason why a lot of the high-functioning, powerful people I know — Judd or Conan or whoever it might be — tend to move slowly and deliberately. They don’t just tell you what you want to hear, because you could potentially break someone’s heart if you aren’t able to give them what you promised.

What’s the most important lesson you’ve learned about acting?

It sounds obvious, but the worst acting is when someone is clearly just waiting to say their line. They’re not in the moment and they’re not delivering it fresh. So I’d try to pause or change my delivery or maybe even rephrase the line just to keep things interesting. Like a good conversation or date, you just want everybody to be present and engaged.

What’s the most important lesson you’ve learned about mentorship? 

Ooooh. That’s interesting. I guess it’s this: If you trust your mentor, it’s the greatest thing in the world. It means that Judd could say — and this didn’t necessarily happen — “That scene you love doesn’t work, and you need it cut it.” And because it’s Judd, this comedy giant, you can just go, “Okay.” [Laughs.] It’s great.

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What’s the most important lesson you’ve learned about show business as a whole throughout your career?

That’s a good one. I wonder if people on my podcast feel like this is as hard as I feel it is.

[Laughs.] Sorry to turn the tables on you.  

No, are you kidding? It’s a dream come true. I love this. The greatest lesson I’ve learned about show business is that if you got into it to be famous, rich or get laid, you’re doing it wrong. [Laughs.] Everyone I know [in the industry] who is interesting and very, very good at what they do is uncomfortable at swanky parties. They’re just people trying to make the art that they would like to see.

And, finally: Tell me about the time you laughed the hardest.

We were in Hawaii with friends recently at a Ram Dass retreat, and we found someone that had a laptop that could hook up to a TV so we could watch my HBO special. We got stoned, and I’ve never been stoned and watched my own comedy before. But everybody wanted to watch it, and that can be a little awkward, so I thought I’d get stoned to see if that made it any easier.

Not only does it make it easier, but because I’m such a lightweight when it comes to marijuana, I was watching and pretty high and thinking, “This guy gets exactly what I think is funny! This guy is saying everything that I think is funny!” It turns out that my favourite jokes when I’m sober are different from my favourites when I’m high, and I was dying at bits I maybe didn’t appreciate until I’d seen them stoned. I think I was laughing harder than anyone else in the room.

Crashing airs Sundays at 10:30 PM on HBO Canada.

Images: HBO Canada