Crashing Season 3: Pete Holmes And The Validation of Rising In The Comedy Ranks

Fictional Pete (or “FP” as real Pete Holmes calls him) is still looking for his “big break.” What exactly constitutes a “big break” is all relative in the stand-up world. Through two seasons of Crashing, Pete has earned the respect of his peers as he hustled through the club scene, has been reluctantly championed by the likes of Artie Lange, Bill Burr, and Jeff Ross to name a few, and landed a college tour, though it fractured his relationship with his girlfriend and fellow comic Ali (Jamie Lee). Crashing Season 3 begins with a montage of Pete acing his college tour, which gives the comedian a budding ego.

“There are people that I know that they don’t get ‘breaks,’ they get like, sprains,” Holmes tells Den of Geek of the roller coaster stand-up circuit. “They haven’t broken into show business, they’ve sprained into show business and they go around acting like they’re like a new person, like don’t look me in the eye because they got some small bit on TV, or whatever it might be. It unlocks this part of you that was egotistical enough to even want to be a comedian, and then you get this validation.”

Pete still has a few “sprains” ahead of him before he can achieve his goal of having a place at the comedians table in New York’s iconic stand-up haunt The Comedy Cellar. Crashing Season 3, which premieres Sunday, January 20th, finds Pete building towards the goal of being “in the scene” by leaving his comfort zone and embracing his egotistical side. We sat down with Holmes to discuss a new relationship in the show that changes Pete’s outlook on his career, sacrificing artistic freedom for lucrative gigs, and the process of writing Crashing.

Pete’s career is starting to stabilize as season two ends. Where do we find him when season three begins?

As one of the writers, we had to decide if season three was going to be just about Pete being on the college tour because that was certainly one of the ways we could have gone —  it is interesting living out of a suitcase. In the finale of season two he’s gotten all these colleges, but we decided instead to start season three at the end of that tour with Pete coming back to New York with an ego. It’s the first time we’ve seen Pete having an ego.

Pete suddenly has an apartment, and that certainly changes the dynamic of our show, he has a little bit of money, so that he’s not broke, and then he has a little bit of an ego. So that was sort of the driving force of the whole episode. Then he ends up attracting a girlfriend that’s attracted to his ego, which I think is really fun, as opposed to sort of that meek country mouse sweet boy that I like, that we’ve seen in the first two seasons. We now see a Pete in a camouflage G Star Jacket.

And he gets his first house guest!

And my first house guest, that’s right! I meet Jaboukie [played by comedian Jaboukie Young-White] who’s incredible and very young, so he’s basically playing a version of himself, a little bit younger. I meet a character and I think that I’m at a place where I can be the Artie Lang to someone else, where I can have someone else crashing on my couch. When really, in show business, my experience has been that you have to make it about 15 or 20 times. Like, it really is a long game. It’s not what you see in the movies.

Pete does have a bit of success this season, and he has to make choices about doing lucrative gigs or pursuing the kind of comedy he finds creatively fulfilling.

In a lot of different lines of work, there come opportunities where you might be perfect for something and they might be lucrative, but they might not necessarily be where you’re at artistically, or creatively or just personally. Pete sort of has like a vestige from his past, which is the Christian market for comedy shows. The Christian comedy market. That’s a real thing.

That sort of comes back, not to haunt him, but to challenge him. So on Crashing, we always want to tell stories about stand-up that you’re not used to seeing, whether it be handing out flyers or doing warm up or colleges. There are hundreds and hundreds of comedians that you’ve maybe never heard of making very good livings only doing colleges. Some of them only do colleges their whole lives, they’ve found their niche and they do it, and they’re happy and they succeed in that way.

So another market like that is the Christian market. I really have to tip my hat to Judd Apatow. I told him we wanted to do it, and he wanted to do the Christian tour and he had the great idea that I immediately agreed with, which was the joke will be that it’s the greatest tour in the world. You hear that a comedy show is going to do the Christian scene, you think it’s going to be hammy and stupid and we’re gonna be making fun of everybody. We went the other way real hard, which was that it’s a wonderful tour, but there’s just a couple things, understandably, that you can’t talk about.

But then Pete has this girlfriend who’s challenging him to be more honest and more bold and the comedy scene itself is telling him the same. But the people who are paying his rent are saying, “Don’t talk about this, or this, or this.” Very small things, but he ultimately has to make a choice.

Read More: In the Comedy Cellar with Judd Apatow and Pete Holmes

Madeline Wise plays Pete’s love interest this season, Kat, who isn’t in the stand-up scene. Wise has a theatre background more so than a comedic background. How did you end up casting her and why did she feel like a good fit to bring Pete out of his comfort zone?

I don’t want to say Madeline is our first real actor, but she’s our first like, actor, actor that I got to be in multiple scenes over multiple episodes with and I have to say that was a real delight. We sort of pride ourselves on being the show that brings comedians in that may or may not be experienced actors and we love working with them. They’re amazing improvisors, and they’re talented natural actors. But when I was working with Madeline, somebody that for all I know came from like a Samuel Beckett inspired play, I’m like, “What is going on here?”

She’s the real deal in that way. I think she elevated everybody that she acted against. She certainly helped me just watching the level of presence and intelligence and decisiveness that she brings to her performance.

She came in to audition and just blew me away. It was one of those situations where we were like, “Well, we’ll rewrite the part, ’cause she’s unbelievable.” She’s been, you know, I don’t want to say laying low, she’s been killing it in theatre, but to find somebody like this and bring her into TV, we’re gonna look so good just for finding her.

How does Kat impact Pete’s life and career?

Pete dated Ali, who was telling him what the harsh realities of the world are, and then he dates Kat, somebody that’s like, “If you want it, you can get it.” I think that’s really essential to either have a friend like that, or a girlfriend like that, or hopefully in the best case scenario, just a voice inside your own head that can carry you through your dreams.

But in this case, Pete needs someone writ large that can say, “It’s not embarrassing to want to be famous. It’s not impolite to want to have people know who you are. But if that’s what you want, you should be honest.” Like, she’s all just about like, just be honest.

Whereas everybody else in Pete’s life, he tries on the jacket, he thinks the jacket’s cool and they all tell him it’s stupid. The jacket obviously is a metaphor and then he meets Kat and she’s like, “I like that jacket. I think that is who you are.” Pete’s trying to grow and become this new thing and she’s the only one that thinks he doesn’t look ridiculous when he does it. That’s important. 

Read More: Crashing’s Jamie Lee on Going From Writers’ Room To Co-Star

It seems like a lot of the material, even in the quieter moments in the show could be fleshed out into your larger stand-up set. How do you kind of differentiate what you want to put in those actual stand-up scenes, versus some of those character?

That’s so interesting, and it’s a nice compliment you’re giving me. Sometimes I watch The Simpsons and they’ll say a joke, and I’m like, “That’s a perfect New Yorker cartoon.” Like, it’s dry and it’s subtle, and auteured and I’m like, yes! But they put it in The Simpsons, which obviously isn’t going for that sort of laugh. So, similarly we had to choose our moments where it was like, “This one seems like a good joke for a scene, and this one seems better for stand-up.”

In stand-up you have the benefit of being able to realistically stack five or six or seven funny jokes in a row, whereas unless you’re doing something big and wild like Ace Ventura: Pet Detective, it’s hard in a realistic way to show a scene where it’s like, “Everything everyone says is a joke!” Without losing some of it’s sincerity. So we would save a lot of those runs for the stage.

Last question: Do you always walk up to The National when you perform?

[Laughs] On my specials I do. I’m happy to say I’m friends with Matt [Berninger], the lead singer of The National, and his wife Corinne. When it comes to TV, you can’t afford anything; if you want to play a song, you’re eating up like a third of your production budget unless you’re friends with someone in a band and you can say, “Can you please cut us a break?” So thank you, Matt and The National for giving us a break so we can use your music on my specials. I can’t get The National on Crashing. Judd thinks it’s too mopey. Sonofabitch.

Crashing Season 3 premieres January 20th at 10:00 p.m. on HBO.