Pete Holmes Knows How Hard It Is to Buy a Gift for Celebrity Chef Rachael Ray

The star of 'Crashing' talks divorce, competition in comedy, and getting engaged in a hot air balloon

Stand-up comedian "Pete Holmes" played by Pete Holmes

Stand-up comedian “Pete Holmes” played by Pete Holmes. HBO

With Crashing on HBO, Pete Holmes adds his contribution to the already hefty stockpile of television shows—mostly produced by Judd Apatow—written by and starring comedians about comedians who share their names. Crashing’s premise, “a comedian trying to get back out there after his divorce,” is already the exact logline both of Louie and Curb Your Enthusiasm.

And yet, there is something infinitely endearing about seeing Pete Holmes on screen as he lopes through misfortunate after misfortunate like a Labrador retriever. I was one of the few, loyal fans of the dearly departed Pete Holmes Show on TBS, in which a stand-up style monologue unrelated to current events was followed by sketches and celebrity interviews, usually with other comedians. When I met Holmes in the lobby of the Bowery in New York, I mentioned that my Pete Holmes Show t-shirt had become a soft, well-washed favorite for me to sleep in. “It’s hipster now!” Holmes said. “I should start wearing my own. That would be double ironic.”

Everything Pete Holmes says is delightful. Just look at his face. He is the human personification of a balloon, of a professional sports mascot, of the aforementioned Labrador retriever. Upon meeting him, it’s immediately obvious why his initial career plan was “youth pastor” (a former ambition shared by “Pete Holmes” in Crashing). It’s also apparent that he didn’t end up too far. Sure now Holmes proselytizes about smoking weed and how silly the name “Lenny Kravitz” is when you think about it (the coolest man in the world is named LEONARD KRAVITZ!) but at its heart, Crashing is a show about faith: the fictional “Pete Holmes” relies on the goodwill and community of those around him while he rebuilds his faith in other people after betrayal. And yes, it is delightful.

OBSERVER: So what did you learn from The Pete Holmes Show?

PETE HOLMES: I mean, I learned a ton. I think the main thing I picked up was how to manage an office because comedians are good at comedy—hopefully—and then they get TV shows and then they have to quickly, on their feet, learn a lot of business administration, which you wouldn’t think. You really are. I would call my friends of mine who are businessmen and be like, “What do you do?” And they use all these terms about “You need to check in.” “You need to give incentive.” “You need to reward them.” “You need to withhold reward,” or whatever it was. It wasn’t to motivate the writers per se. It was to keep everybody happy. Because people would feel neglected on the Pete Holmes Show. People slip through the cracks. Of course, I didn’t know. I was in my own world. Very different. But what I learned was you need to make sure the office politics—somebody’s taking care of them.

That seems strange how the industry rewards someone for being a great stand-up comedian with like, a high-level office position.

It’s like giving a waiter a restaurant. It’s a bizarre thing. You’re a very good waiter, and then you have to do the books and stuff. It’s very different. It’s not THAT hard. But that was the thing that surprised me was that at the end of The Pete Holmes Show I found out that morale was low in the writers’ room at times. I just had no idea because I wasn’t in there very much.

Lauren Lapkis as Pete's soon to be ex-wife

Lauren Lapkis as Pete’s soon-to-be ex-wife. HBO

Crashing is obviously a personal story. Was it cathartic to revisit those moments, or is it so far in the past that it felt like it happened to a different person?

Well, it’s been ten years. I think in telling the emotional story we changed the facts a little bit. But in retelling the emotion of it, you notice that it still does hurt in ways. There’s this—we’re liturgical beings and ceremony, and “This is my wife.” that it hurts more than it ought to. If that makes sense. It was just a person. I remember when I got divorced, people were just like, “It was just some stranger you met. You didn’t grow up together or anything. It’s just some lady you met. You’ll meet another lady.” But for some reason, the psychological ties are such that it leaves a wound greater than the sum of its parts.

In doing the show, I’ve done a lot of therapy and a lot of talking about it and processing on my own. And then I think the final two steps were making the show, which was like… If therapists could, as an exercise, have people that had something bad happen to them write a story from the other person’s perspective, to empathize with them. It’s remarkable in offering closure. I really tried very hard, and I think succeeded in making Lauren Lapkus, my wife’s character on the show, very sympathetic and actually somebody you’re completely understanding of. You get why she wants to leave. It’s not because she hates Peter because he’s an alcoholic or hits her or something horrible like that. She’s not the right fit, so we try to make her very understandable. And then I actually just got engaged, and that was strangely sealing.

Congratulations!

We got engaged on a hot air balloon, which means there was a man I didn’t know standing six inches from my face.

Did she know you were about to propose?

She absolutely knew. When we started dating, she mentioned she always wanted to go on a hot air balloon, and I was like, “Oh, that’s how I’ll propose at some point.”

You said that, out loud?

Oh, I didn’t say that. I wrote it on my phone.

In fact, if you print anything—I don’t know if you’ve watched the show but maybe the most useful thing I can offer is, keep a note in your phone for your girlfriend. Like random things she says. [laughs] Ring size, birthday—in case you ever flip out and, I don’t forget her birthday, but at the beginning, you might forget—and then gift ideas. I’m terrible at on-pressure gift or ideas.

You can’t be—you have a gift right there! [Note: Holmes has a vinyl record next to him that he’s giving as a gift]. What album is that?

This one? “Let’s Get Small.” This was because we were going to Rachael Ray, did something on the show.

The celebrity chef.

The celebrity chef Rachael Ray. Yes. Because, at some point, “Pete” gets a job working on her show. And one of the best things we did on “Crashing” was work with Rachael because she was like, “Come on over for dinner!” And we went to her house for dinner. I brought the writers’ assistants. I think the LA thing is you’re supposed to bring the executive producers or whatever, but…

The writers’ assistants are the people who would appreciate it the most.

I was like, “I’m going to blow your heads off.”

They need free food also.

They need free food. Yeah, I like to think they can afford sandwiches and stuff but like a meal with Rachael Ray is something that you never get a chance to do that. We’re going to do it again but they got snowed in upstate. They got snowed-in and winded in upstate. But I’m doing her show this morning so I’m still going to give her the gift.

It’s a thoughtful gift. You didn’t just give her a scented candle or something. 

Well, this is for her husband actually. This is for her and her husband. Her husband loves vinyl, and we got her a box of chocolates. It’s stressful when you go to Rachael Ray’s house for dinner. You want to bring something edible that’s amazing.

You don’t want her to take a bite and be like…

Yeah. Not yum-o. [laughs] But it was nice. We’re doing it another time.

So, speaking of having comedians and people play themselves on the show when you wrote it, did you know specifically, like “Oh, I’ll definitely get T.J. Miller”?

I mean, most of the guest stars were friends of mine in real life. TJ is actually one of the few examples of people that really did come and visit me and help me right when my actual wife left. He was filming the movie She’s Out of My League in Pittsburgh, and I was here in New York.

I remember that movie.

Yeah. [Laughs] On the poster he got a six. Like they rated people on the poster of the movie and he was a six out of ten.

He's at LEAST a 7

Come on, he’s at LEAST a 7. Dreamworks

That’s a little rude.

I know! It was offensive. So my wife leaves, and this was in real life. And he was like, “Come to Pittsburgh.” He put me up in the hotel that they were at and I stayed with them for three or four nights or something. It’s just so crucial. That’s one of the things everyone asks, if I buy the premise of the show or if it seems artificial that comedians would ask someone to stay with them. Well, that IS what happened. People do it all the time.

So I don’t know where people get the idea of comedians being very backstabbing and competitive. There is some competition, but almost everyone—my circle of friends—all are working comedians.And all of us, whenever one of us got a job or someone needed money or someone needed a place to stay, we were constantly helping each other.

The people that I knew—this is all New York, for the most part, because that was when I was coming up—that talked shit about other comedians, they all quit. They’re all gone. They stopped doing it.

They were probably not that funny.

And that’s what made them bitter, but it is that sort of thing where it’s like, “You could have been working on your act instead of getting drunk and complaining that Aziz got Premium Blend so quickly.”

Aziz is really good!

Aziz IS really good. He shot up really quickly. And I remember him specifically catching a lot of ire. And then I was sitting at a table where three people were just like, “I can’t believe he’s on the hot list on Rolling Stone.” And I was like, “I think I need to get away from this.” [Laughs] Like, you just need to slowly back away. And that’s when I started becoming friends with John Mulaney and Nick Kroll, and all these guys who are just like—They just do comedy because they kind of have to. It’s not like a politics situation.

And I think that something similar with John Mulaney’s stand-up and your stand-up is that it’s not like the jokes are mean and targeted, they’re just funny on their own.

I love Mulaney, so any comparison to him is very kind. Thank you. I agree. That was The Pete Holmes Show. I think that’s why I got a talk show. In fact, I know because Conan O’Brien said, “You don’t do comedy AT anyone. You’re just kind of joking around.”

So back to Crashing: has your ex-wife seen any of it? Have you kept in touch in any way? 

No. My secret hope is that she’d watch it and appreciate what we were talking about earlier. That I was very careful to make her the character that is inspired by what happened to me. It’s not her. The character is very much Lauren Lapkus and we changed everything.

We haven’t talked since we split, and that was almost exactly ten years ago. Not exactly, but it was in 2007. She probably won’t watch it. I probably will never hear from her. But if she did, I would be like, “Don’t you see? I forgive you and I get it. I tried to make it from your perspective as much as it was from mine.”

I don’t think she comes off as a bad person.

She IS a good person. She just wasn’t in the right relationship. She was 24 when we got married, and I was 22. And when I think back to who I was, I’m like, “What? What are we doing? That’s insane!”

Twenty-two is very young.

I meet 22-year-olds all the time and they seem just like tall infants. It’s crazy. My wife was 24 when she was like, “I’ll marry this guy forever.” She thought I would straighten her out. I guess she was wild. She never seemed that wild to me. But she thought I was good for her. But then, when we split, it such a brilliant move on her part—she’s breaking my part and turning my whole world upside-down, she’s like, “I really think you’re going to be one of the greats.” She threw that in.

It’s kind of what the show’s about: That line where Leif, the guy who has sex with my fictional wife, he’s like, “You don’t belong here.” And there’s something interesting about these things that we never asked for to happen sending us to where we always wanted to go. So, the tragedy of my divorce was that I thought I was happy. Now I’ve just filled out the suit of who I am in such a way that I look back and like, I don’t know if I could have done that work if I stayed in that understanding of myself.

Artie Lang in 'Crashing'

Artie Lang in Crashing. HBO

Are you one of those people who believe everything happens for a reason?

I’m a person who believes everything happens. When people say that I feel like they’re saying it can be a little bit trite, meaning there’s a deeper way to believe that. Like even your death like “It happened for a reason! Look, I sprained my ankle but I stayed home and that’s when I found the five dollars!” That’s typically how it’s understood, but I believe it’s all in the game, the suffering and the loss. Even unnecessary, insane loss can be part of it too. Not just things like this where your wife leaves you, but then you get to have your dreams come true. I also believe that tripping on the stairs probably happens for a reason. I think everything’s your teacher. That’s a better way to put it.

So, in your stand-up and in the show, you talk about how you were planning on being a youth pastor.

Yeah. And when I became a comedian, my mother said, “Close enough.” [laughs] It is the same skill set, which is funny because declaring you want to be a comedian is a weird declaration. Like if you can imagine. Because you hang out with your friends, and they’re funny too. And you’re basically saying that all those laughs you had, you owe me thirty dollars. It’s like, “You owe me cash. I think I’m better than you.”

So you kind of keep it to yourself and there are these little gateway aspirations, and one of them was definitely to be a newscaster. You stand in front of people. You entertain them. And you hopefully leave them feeling better than they felt when they came in. TJ on the show says, “You’re better than a newscaster because you’re not lying.” [laughs] That’s how TJ is. You want to slowly work your way into comedy and that’s what I did. Improv and then cartooning, and then one day you’re out of the closet and you’re like, “I’m a comedian.”

When you’re writing it, do you have any vanity about writing a character named “Pete Holmes”?

It’s funny. Any time I caught myself shying away from something—Like, I remembered Lena in Girls saying that—there would be four takes for one scene—she would use the least flattering take. And I really thought that was inspiring. Especially with comedy, you’re trying to showcase something that’s wrong or weird or strange about you, and that’s actually what gets me excited. If we get a season 2 [knocks on wood], it’s going to be really interesting to start going into the psyche of this people-pleading boundary-less person that is kind of secretly very driven and likes comedy more than people. And that’s sort of the stuff that I like that they do on Girls.

So, similarly, every opportunity that we had—and a lot of them didn’t even make the show—we had characters tell Pete that he sucks or that he’s not funny and really go to town, like make fun of me. And it would often be me as the producer telling the actor what to say about me. So, we couldn’t assassinate my character enough. But we found, in the editing, that we needed to take some of that out because I think there’s a certain amount of investment you have on the character that you don’t want to see him just get slapped around.

Yeah! His wife just left him! 

Yeah, I know. But that’s why everybody’s so mean. The thing that I like, and I think this is appropriate for your publication, is the reason we go to New York—this is factual—it’s where I started, but it’s also a good metaphor. It’s like comedy and New York don’t need or want you. So if you leave comedy or New York, neither would notice. Like it just keeps going without you. People get into their cars and be like, “Fuck you, Manhattan!” But Manhattan just keeps on going.

So on the show, with the car getting towed, and the mugging—all of those things happening in one day isn’t very realistic, but that’s the way it feels when you’re in New York trying to make it. And you need someone like Artie to be this unlikely Yoda, and then pass you onto the next person.

Pete Holmes Knows How Hard It Is to Buy a Gift for Celebrity Chef Rachael Ray