Judd Apatow And Pete Holmes Discuss The Unique Comedy of ‘Crashing’

Judd Apatow and Pete Holmes first met on a podcast: Pete’s You Made It Weird, live from SXSW in 2012. Instead of making it weird, they kept it real, developing a wonderful working relationship. In fact, Holmes first pitched the idea for Crashing to Apatow as a bit on The Pete Holmes Show for TBS. And now, in August 2018, they’ve just wrapped filming on season three of the HBO series, which charts Pete’s early years in stand-up comedy.

Of course, there are lots of shows on TV and streaming devoted to the lives and careers of stand-up comedians; so what sets Crashing apart from all the rest? Decider asked them just that, during their lunch break on the set of Crashing at The Comedy Cellar.

“I hope what makes it different is mainly Pete,” Apatow told Decider. “He’s just so unique. The type of person you don’t see on TV that often. With a lot of these shows, it’s about the main person you’re following, and he’s certainly an original.”

DECIDER: Where does season three take Pete?

Apatow: This is the first season where he’s actually funny. We did pretty well with two seasons where he was trying to learn how to be funny. And this is the first one where he has a real gig. He’s traveling the country doing colleges. So we explore how you get to a certain place where you have to decide if you’re going to be hacky, or unique and original.

Season 2, Episode 7 opens up this comedy can of worms for Holmes when he showcases for NACA, the organization that books entertainers for colleges across the country.

Holmes: Well, you can be very successful being, I like to say broad. Only because a lot of things that are hack is my own material (laughs). So I want to call it broad. But it is hacky. Here’s the funny thing, though. I remember the day we were taping, and I was doing my most broad set, and the artist in me is saying, this isn’t my best stuff. And a lot of the crew was like, ‘That was your best set! I loved that set.’ So there’s something…

Apatow: Accessible.

Holmes: Accessible!

Apatow: Because it’s been done so much.

[Laughs]

Holmes: It’s interesting at this point in Pete’s career, he’s deciding what kind of comedian he’s going to be. That might sound privileged. Like he’s got some money now, he’s got an apartment now, he has the freedom — but really, any comedian, when they’re onstage, has the freedom to choose what kind of jokes they’re going to tell. And he’s really being pulled in a lot of different directions.

Apatow: We’re just trying to stay true to the character and the world, trying to be as accurate as we can be. It’s an opportunity for us to explore the comedy scene, but also the type of people that want to be comedians, and the different struggles that they go through, the different emotional journeys you have when you’re trying to be funny and you’re also trying to grow up in some way.

Speaking of accuracy, you’re a disciple of Garry Shandling, and congratulations on your Emmy nominations for your documentary on Shandling.

Apatow: Thank you, sir.

But as such, we know you really want to get accurate, and to the real heart of the story. When you’re watching other TV shows or movies set in the world of comedy, what bothers you?

Apatow: What bugs me? I think that it’s very hard to show the behavior of comedians. So it’s a little easier for us, because most people are playing themselves, and if I just roll the camera for a while, and people relax, they might start sounding like themselves and being funny, like the way they are. I think when it’s too tightly scripted, it can lose its naturalness, and that’s something that we’re always struggling to try to figure out how to do well. How do you capture what the vibe is in a comedy club, and the way they interact with each other? And for us, we work really hard on our scripts, but we also try to stay loose enough that people can bring their real energies and personalities to it.

Holmes: I think the reason there’s so many shows about comedy is because the job of a comedian is to figure out who you are, communicate that, and have it be accepted. So that’s very relatable. A show about chefs would be the same thing. Or a show about teachers or mothers would be the same. But comedians have the added benefit of being able to be funny. So I think that’s why we keep seeing it over and over. Our show is trying to do something a little bit different from the shows that I have seen, like Louie or Seinfeld, in that we’re showing in real-time — in fact, Judd’s always trying to slow it down — what it’s like to start in comedy.

But not like The Marvelous Mrs. Maisel does on Amazon?

Holmes: I’ve only seen the pilot of Maisel. I thought it was wonderful. I saw the pilot for I’m Dying Up Here and I read that book, and I thought it was wonderful.

Those are both period pieces, though.

Holmes: That’s what I mean. I feel like stand-up’s just a really good engine to put in whatever story you’re trying to tell. Marvelous Mrs. Maisel, I don’t think, is really about stand-up in the same way that our show is. And I’m Dying Up Here is different. They’re all different, even though they’re all similar. We just love it because they’re emotionally honest people. It’s like The Sopranos. He’s talking to his therapist, right? We talk onstage. You have that same, ‘Oh, he’s being real’ device. That’s something we do in this season a lot, which is my character’s in a new relationship, and you see how he really feels a little more when he talks about it onstage so he can kind of leak out the truth.

Some comedians took issue with season one in that Pete Holmes, when he wasn’t funny yet, could crash with the likes of a Sarah Silverman.

Apatow: I don’t think that’s inaccurate. I was very unfunny, and there were plenty of people who were really nice to me. I’m always shocked at who would sit with me, and talk with me, give me gigs when I was really bad. And that’s what I like about comedy. I think a lot of comedy people have good radar for who’s funny, who’s worth their time. And they see promise in people. There’s a lot more camaraderie than people expect. Believe me, I’m sure Artie Lange has hung out with a lot of weird people. Not just Pete. And Sarah’s always been very kind to people, and likes helping people out.

Will Crashing have a #MeToo episode?

Apatow: We do have an episode where we show Ali (Jamie Lee) go on the road, and what it’s like for a comedian to travel to another town, and how they’re treated and what they go through. So in that episode, we’ve attempted to give you a sense of what happens and how hard it is for women.

What conversations do you have with Pete to make sure he’s playing an earlier version of himself? Since in real life, he does have an HBO special, he’s married, and about to become a father.

Apatow: He remembers his pain. He doesn’t seem to have any trouble. No one wants to see a show about the new, arrogant Pete Holmes. The new, high on his hog HBO star Pete Holmes. Or maybe that’s the last season. As he turns into the Pete Holmes of Crashing. Maybe worlds will collide. And we’ll catch up with reality.

Holmes: I don’t know if there’s anything easier than being less confident. You have the confidence to know you can be less confident at any moment.

How do you reconstruct live comedy for TV at the Comedy Cellar, Gotham Comedy Club or Hollywood Improv when it’s an audience of extras in the middle of the day?

Apatow: It’s funny how it works. If you get any 100 people in a room, and you tell jokes to them, they’re pretty close to a real crowd. Every once in a while, you might have to say “give them more energy” or sometimes “give them less energy” because sometimes we don’t want them to do well, and the issue is, they do well anyway. But for the most part it works. Everybody wants to laugh. Even extras.

Sean L. McCarthy works the comedy beat for his own digital newspaper, The Comic’s Comic; before that, for actual newspapers. Based in NYC but will travel anywhere for the scoop: Ice cream or news. He also tweets @thecomicscomic and podcasts half-hour episodes with comedians revealing origin stories: The Comic’s Comic Presents Last Things First.

Watch Crashing on HBO GO or HBO NOW