Pete Holmes Credit: John Sciulli

On HBO’s Crashing, former Chicago comedian Pete Holmes plays a green stand-up named Pete Holmes (role of a lifetime) who struggles to find his footing after his wife cheats on him. Their divorce leaves Holmes homeless and he resorts to couch surfing. Through a variety of humiliating misadventures he ends up in the company of more established comics such as Sarah Silverman, Artie Lange, and T.J. Miller. They pity Holmes enough to allow him to spend the night, but the naive comic also gives them an opportunity to pump up their own egos by sharing their stand-up wisdom. Unshackled, Holmes gigs nightly and begins questioning his strict Protestant upbringing. The show’s second season, which began January 14, opens with Holmes, despite his lingering Christian guilt, enjoying a veritable bacchanalia of booze and women at a nightclub called the Hole with some new comedy buddies.

Crashing closely resembles Holmes’s early years in comedy. In 2007, he and his wife divorced after she cheated on him. After moving to New York from Chicago, he performed prolifically while evolving from doofy, self-described “fun dad” to doofy, introspective comic on his way to becoming an atheist. Fittingly, he titled his two comedy albums Impregnated With Wonder (2011) and Nice Try, the Devil (2013). On his seven-year-old podcast You Made It Weird, Holmes talks comedy, sex, and God with comics, actors, musicians, and filmmakers. He hosted The Pete Holmes Show, which aired after Conan on TBS, from October 2013 through June 2014.

Crashing, which is coproduced by Judd Apatow and employs fellow former Chicagoans Beth Stelling and Emily Gordon as writers, held its season-two launch party in town on January 14. We reached Holmes over the phone in his downtown hotel room and asked about stand-up comics playing stand-up comics on TV, the status of his relationship with his ex, and his feelings toward friends in comedy who currently face allegations of misconduct.

In the first two episodes of Crashing‘s second season, your character appears to be the happiest he’s been in a while, followed by the saddest he’s been, to the point where he has a one-night stand and then hangs around the woman’s apartment alone the rest of the day. What informed the decision to go so big on both ends?

That’s what life feels like to me: really high highs and really low lows. One of the things the show is about is finding humor and a way to enjoy the low times as well as the high times. When you’re trying to become a comedian, there are so many low points, especially when you’re trying to redefine your life at the same time. I have a lot of people who have just seen the promos and stuff that are like, “I [also] accidentally said ‘I love you’ on a first date.’ ” People are relating really hard to that level of vulnerability, and I like putting stuff like that under the spotlight. I think a lot of times, especially in American comedy, we tend to shine the light on winning and killing it and success. I’ve always enjoyed shows that dip into more complicated space from time to time. I think people can relate, even if they’re not a comedian, to someone newly single trying to find his way. Whatever you’re going through can be projected onto that empty vessel.

There are lots of shows in which stand-up comedians play stand-up comedians, the obvious example being Seinfeld. How does the history of this well-worn conceit affect your approach to telling stories?

A good stand-up has the same goals as pretty much any person, meaning that they want their thoughts and feelings to be validated. Even if you’re a chef or an architect or a homemaker or a school teacher—it doesn’t matter—you still want what you think and what you feel to be heard, appreciated, and understood. That’s one of the reasons why we see some of these shows about stand-ups. As an added bonus it’s always believable for these characters to be funny. It’s not like a pretend reality where there’s a live studio audience or something. I love those shows, but I’m just saying we’re not making jokes because it’s a TV show, we’re making jokes because comedians make jokes all the time. Even during my real breakup I was making jokes. It’s just part of our DNA. So it’s fun doing scenes with Artie Lange and Rachel Feinstein and Jamie Lee. It’s like, no matter what you’re going through, even something as awkward—and I agree it’s verging on pathetic, hanging out at a hookup’s house, overstaying your welcome—you still make jokes in that tension. That’s one of the reasons why we see so many shows about stand-up and probably will for a while.

On the show you become friends with Leif, the free spirit your wife cheats on you with. And before that you have zero history with him. So when writing the character of Leif, how much of that relationship is wish fulfillment—the possibility of becoming friends with the man your wife slept with?

It’s definitely a metaphor, meaning Pete is trying to make friends with unwanted change—which is also known as pain or suffering or shitty things. [We] agreed it was funny to continue that relationship so that Pete can also have this voice of another perspective. I like to joke that Leif represents my attitude now, meaning he sees the beauty in things, he has a zoomed-out perspective when it comes to loss or the grind of trying to do stand-up. It’s nice to kind of be able to time travel and speak to myself back then with what I might say to me now.

“We need to be careful when we speak and when we listen, and it’s a time for listening.”

—Pete Holmes

You mention on the show that you miss the days when stand-up comedy took the form of joking around with your friends at an open mike. Chicago’s famed Lyons Den open mike springs to mind. Comics such as Kumail Nanjiani, Kyle Kinane, Hannibal Buress, and T.J. Miller started there. How did your time at the Lyons Den, when the stakes were significantly lower, differ from the feeling you have now when you perform stand-up?

One of the things that makes Chicago a great city to start in is that the people doing comedy here just love doing comedy. That kind of sounds backhanded. I mean it in a very sincere, loving way. This isn’t overtly a show-business town. It’s a real place, it goes through real seasons, it has people who have real jobs—

Wait, what’s a “real” job?

I just mean that all of show business isn’t really a real job. I live in Los Angeles. Try to find an architect in LA. I mean, I don’t know too many teachers. You don’t really meet a carpenter. You meet a guy who builds sets for a TV show. You don’t necessarily meet a guy who builds tables, you meet a set designer, you know what I’m saying? Your feet don’t really touch the ground as much in Los Angeles. So when you have these cities—I think Chicago’s one, I think Austin can be like this, Portland is like this—that are more grounded, the people doing comedy aren’t doing it just to make it. Like, they’re not trying to put together five minutes in hopes that they’ll get cast on the Will & Grace reboot. They’re doing comedy because they’re freezing, waiting for the Irving Park Brown Line, and they want to do something at night. They do it for the love of comedy. We kind of touch on that in the first season—there’s a lot of $2 Miller Lites and there’s a lot of hanging out. I prefer this now just because it’s the phase of life I’m in—but when I was at the Lyons Den I didn’t ever think I would get any better than that.

Looking at the list of performers from the Lyons Den, you get the impression the comedy scene was very dude-centric. Recently, a local comic named Meredith Kachel used statistics to empirically demonstrate men get far more bookings here. What are your thoughts on the barriers to entry for women in the comedy world?

I look back on that time and you’re right, there was a lot of dudes. I don’t know what that was, but I will say [the trend is] starting to correct itself. I can’t speak to the female experience, but I can quote some of my friends like Jamie Lee, Beth Stelling, Emily Gordon. It’s just less weird, you know what I mean? I think there was a time when people would look sideways at a female comedian getting onstage. It’s certainly not equal yet, but I think we’re working our way that way. And when you see so many people naming Maria Bamford, Natasha Leggero, Tig Notaro, or Sarah Silverman as their favorite comedians, that’s a wonderful thing. So if there was a Lyons Den today, I would think that it would be more of an even split.

We wanted to address [the divide] in the second season. Pete dates a comedian, but we kind of address it by not addressing it, to be honest. The character of Ali [played by Jamie Lee] is a driven, funny, successful comedian, and there is no, like, very special episode of Crashing talking about what it’s like to be a girl. In fact, it’s the opposite: Pete is the one who needs to learn from her as opposed to a man swooping in and mansplaining to Jamie about how to do comedy. It’s the other way around.

Given your experience hosting a talk show, what are your thoughts about the format, especially when it comes to interviewing comedians? As in, they come out and the host says, “So I hear you have a crazy car story,” or something to that effect to set up the material.

It’s that way for a reason, understandably. I remember when Conan [O’Brien] and I talked about my talk show. I was like, “What I want to do is have actors on when they’re not promoting something.” And he kind of jokingly said, “The problem is a lot of these actors don’t have anything to say other than promoting what they’re doing.’ ” I think that’s true. It would be a wonderful world if we could sit and really talk with people, but I think that’s what podcasts are for and why they’ve become so popular. The cultural taste has been elevated. We want to go deeper. I think [Stephen] Colbert specifically does a really good job of kind of mixing the two, and Seth Meyers and Conan can do that as well. I see Jimmy Kimmel doing it. But at the end of the day—

You just named every talk show host minus one or two notable exceptions, like Jimmy Fallon.

I don’t watch everybody, but that wasn’t, like, shots fired. That was just me trying to remember everybody that I’ve done recently [as a guest]. As you talk, behind them is a producer saying “30 seconds”—which is something I never fully understood. I guess it’s to preserve the energy of the host, but when we did a talk show I would talk to the guests for, I don’t know, 40 minutes, sometimes longer. We would put the extra stuff online. A lot of shows this way shoot it as if it’s live, maybe to minimize the work of postproduction stuff? [Doing longer interviews] never really caught on. It’s almost like the way that cartoons captured something in our collective unconscious. We dream in cartoons, people hallucinate in cartoons. I think the talk-show format is something we’ve kind of collectively agreed on. Like, if Sarah Jessica Parker was on a talk show with me, people would think, “I want to spend seven minutes with Sarah Jessica Parker, five with Pete, I want to see a band, then I want to go to bed.” We’ve been trained to like that. I almost feel that’s reflecting something we enjoy naturally.

When you’re on talk shows now promoting a comedy, how much pressure do you feel to be funny?

I remember Chris Rock saying it’s unfair that comedians have to come on and be funny, because Daniel Day-Lewis doesn’t have to come on and be moving. But I don’t see it that way. Having hosted a talk show and having talked with Conan, I think comedians are at a great advantage doing late night. It’s like doing stand-up but easier. One of the modes of doing stand-up is you have to know where you are, what you want to talk about, where you’re going with this. And when you have someone there with you—I’m doing Conan on Monday, and I e-mailed them four pages of stuff that I’m working on and said, “Just ask Conan which of these premises seem like things he’d like to play around with.” We pick three of them, we get to two of them. You’re saving the producer, who normally has to get on the phone and be like, “So, what’s going on in your life? How are you? Anything major going on? Any stories from the set?” I feel bad for actors just because they might not have the experience writing for themselves.

Jamie Lee and Pete HolmesCredit: HBO

This would seem to be a strange time to be a stand-up comedian given all the allegations of sexual misconduct in the entertainment industry, including in the comedy world. How do you approach this climate?

It’s not so much that it’s a strange time to be a stand-up comedian or an actor or a producer or somebody in the public eye as much as it’s an unsafe time to be a woman. That’s something I’ve been meditating on. Maybe I’m an optimist, but my hope is that all of these stories coming out won’t just be a flash in the pan but will lead to real change in the way we treat each other. A lot of people point out, “Well, men feel unsafe [now].” Well, that’s how women have always felt. Now there really is a system of accountability moving past the shock of “Who did we catch?”

I’m interested in the conversation about if we’re allowed to laugh at people who’ve made mistakes.

Well, what do you think?

That’s something I’m figuring out culturally. You kind of take it case by case. I don’t think anybody’s watching The Cosby Show, but can you watch Good Will Hunting knowing Harvey Weinstein produced it? You kind of have to take it on a personal level. I hope the generation coming up now isn’t going to live in a world where we laugh about the concept of a casting couch or any sort of casual abuse or rape humor that normalizes it. That, to me, feels like progress. Everyone’s being more deliberate in how they behave towards each other. I think there could be a good outcome for all of us.

One of the stories that broke concerned T.J. Miller sending a transphobic e-mail to someone who once considered him a friend. Given your friendship with him and the fact that he was on your show, I’m wondering what your thoughts were when that news came out.

Obviously it’s heartbreaking and it’s upsetting. I haven’t talked to him. I called him the day that the story came out. It was news to me. I didn’t know those details. He is my friend and I love him, but I do think it’s a time to listen right now. It’s not really my place to—we need to be careful when we speak and when we listen, and it’s a time for listening.

You’re staying at a hotel in Chicago under the pseudonym “Gern Blanston.”

Do you get the reference? It’s an old Steve Martin joke. I want to say, on the record, not my idea. I don’t think I need this level of anonymity.

How does your higher visibility affect your stand-up?

People always think I’m joking when I say this quote, but Sinbad once said, “Comedians are funnier when they’re taking the bus.” There’s some truth to that. When you’re flying first class and it’s your first experience going from a touring comedian to a TV person, you want to write jokes about that. You do sort of feel this need to qualify it, because the whole idea of a lot of comedians is “I am just a representative of you.” What I think is more dangerous is when you start telling these unrelatable stories. I don’t mean that as a put-down. I know [Dave] Chappelle does this a lot, but what else is Chappelle going to talk about? I mean, that dude can’t go to the grocery store. I would rather do a joke about the phone book rather than when I met Rachael Ray and we had dinner, which is true. It’s like a fancy watch—just another [hurdle] between you and the audience. The more you can stay relatable while at the same time occasionally flying first class is good. Sinbad was right: I’m gonna take the bus to the airport, dammit.

Given the fact of your higher profile, it’s more likely your ex-wife will see the show and your depiction of your former relationship. Have you heard from her?

No. It’s been over a decade since we’ve talked, and that’s not out of malice. I’m just typically not friends with any ex-girlfriends. It’s just like, “That was a time and let’s move on.” That’s all out of love, I suppose. Especially when your wife leaves you, like, what are we going to chat about, you know? But now that all this time has passed [I’m] curious if she’s seen the show and if she likes the show. Obviously my fantasy would be that she’s proud we didn’t represent her as some sort of monster, that I’ve only ever done the work trying to understand why what happened happened. At the end of the day this was somebody I loved very much, somebody I still feel love for, somebody I hope is happy. Then there’s the showbiz part of me that is like, “I hope she likes Crashing.” So yeah, I’m gonna have to keep holding my breath on that one.

Is there an element of schadenfreude, something along the lines of, “God, I hope she’s super jealous of my success?”

I remember Bill Hicks had a bit like that where some girl dumped him because—I don’t know. He had the fantasy that she would see him on TV from the trailer park. I don’t have that with my ex. It’s more of a—she was so supportive and kind all those years that it almost feels like starting a company in your garage or something, and then at a certain point one of the people left and the business goes on and starts doing well. You don’t look back on the person who left and think, “Well, fuck you!” Marc Maron has a great bit where he’s like, “When my wife left all I could think to say was, ‘Well, thanks for helping out,’ ” and that’s sort of how I feel. We were in each other’s lives at my most anxious, my most vulnerable, and my least funny. I hope she’s happy, and I have a feeling she is. She was always like a nature-loving, jogging, kind of Ralph Waldo Emerson, Thoreau-type person. She didn’t want to be in Chicago. Some people would rather be—and I don’t mean this condescendingly—in the woods. And I get that because, quite frankly, sometimes I would rather be by a lake in the woods too.

I think at this point you’ve quoted five other comedians.

Why do the work of thinking of your own thoughts when you can just remember other people’s?  v

Crashing Sundays at 9:30 PM on HBO