Comedian Pete Holmes’s new late night show, The Pete Holmes Show, premieres tonight on TBS. Holmes built an audience with his podcast, You Made it Weird, an interview show where Holmes talks mostly to fellow comedians about his obsessions: sex, comedy, death, nutrition, and his weird California spiritual beliefs. At its best it feels like a funnier version of the kinds of conversations you usually have at a diner very late at night. What happens when you die? How do you know you’re actually in love? What was the hardest you ever laughed?
The show’s also famous for having produced some breathtakingly awkward moments. During a live episode in San Francisco, Holmes opened an interview with comedian Jon Glaser by reminding him that he’d beaten him in an audition for the voice of the eTrade baby. You sort of have to listen to the audio, because the confrontation that follows is so excruciatingly awkward. I talked to Holmes about what it’s like to build a late night show from scratch, and how he plans to take the intimacy and looseness of a podcast and translate it to the typically more polished world of late night TV.
I saw somewhere online that when you found out the show was green lit, you were like in a really depressing setting, at a Thai restaurant eating alone on Valentine’s Day.
Yeah, that’s true, in Vancouver. [Laughs]
That seems like a weird setting to get really good news.
Yeah, no, it was the weirdest setting. That was a really difficult time in my life, in between making the pilot, which was hands down the happiest time, and then waiting to hear, which I think was a good 6 months later. We were all so happy and really self-congratulatory, and we were kind of unrealistically waiting to hear quickly, and I understand why we didn’t. There’s lots of things to consider, like money and business and time slot and all that stuff that I don’t have any hand in. And it turned out it took 6 months. February 14th was pretty much six months after we shot the pilot and there were so many ups and downs in that six months.
That week I was getting calls right before I was going on stage because I was doing stand up that week. I was just turning ghost white and was just so afraid and so nauseous. And to finally get the answer, eating alone in Vancouver, it kind of felt Kerouacian and kind of appropriate.
I never understood completely why for a lot of standups, the top of comedy success mountain is the late night show. It seems so hard to make a good one. Like I love Conan, but there’s patches of it where I don’t laugh at all.
Conan always talked about putting his bone marrow into the wood chipper of comedy. In that structure, in that sort of “pencils down” scenario of creating a show everyday, I think you get a little bit of a release. Triumph the Insult Comic Dog was a last minute Hail Mary bit that they wouldn’t have done if it were a weekly show. It wouldn’t exist.
So, late night is living and breathing, it’s something that you interact with. It favors a personality that wants to link up with fans in a more personal way and that’s something that I actually want to do with this show. Carson never talked about his five marriages; I would have loved if he did. He’d make a couple jokes every once and a while, but I’d like love to see what would happen if we do a late night show where the host really is uploading his entire being as part of the show.
I was wondering how much you’re going to try to incorporate some of the feeling of your podcast into the show. Are you going to keep asking people to tell you what they think happens when you die?
Yeah. I woke up at 5 A.M. this morning and wrote that down, specifically the “What happens when you die” question. Andy Richter just did our test show, and we didn’t get to any questions, we just talked. It was just two guys talking, and I promise there are people in the audience who wondered how we got to the talking points so naturally, because he’s such a funny guy. I’m really trying to bring the tone and spirit of the podcast into a format that’s doing its best to make sure that we’re slick and polished. I want to keep the fuck ups in the monologue. I want to talk to the audience. I want to keep it as authentic and transparent as possible.
When you’re a kid and you watch late night, it feels like you’re listening in on grown ups having a conversation. And then you get older and you realize its just spring-loaded anecdotes that they’ve prepared. It would be nice to see a show where people are talking.
Yeah, I would really like to see if we could do that, and, you know, the first 28 episodes are about meeting me, meeting my friends. It’s about learning that sensibility, so every guest that we’re having on isn’t promoting anything. It’s not about pushing some movie. Don’t get me wrong, I want people to watch, but I like that sensibility of early Letterman—no one’s watching, they don’t know what we’re doing, they let me get away with this, uh, can you believe they gave me a show? That’s the tone. The headline I’m going for, when people watch the show is, “something’s happening.”
A great thing about your podcasts is that there are occasionally transfixingly awkward moments in it. Is there a way to get that feeling into a late night show?
I really hope so, I mean, I really, really hope so. With Kumail Nanjiani [comedian/Holmes’ good friend] being the first guest, it’s just like, I know we’ll get there. He’s gonna make fun of my ex-wife or he’s gonna ask me why he’s the first guest.
I think that’s a lot more compelling and potentially more awkward and real than, don’t get me wrong, I watched the premiere of Fallon because he had De Niro, and I wanted to see De Niro. But there’s just so many people doing that type of late night so well, rather than compete or kind of join in on that, we’re trying to do something different. So, if we can have a Glaser moment, or even a moment like when Chris Gethard did You Made it Weird, and we had that awkward moment where he talked about how close he came to pitching a show for Conan…
What’s the hardest you’ve laughed all month?
We were working on a monologue and this will give you a good example of how we’re trying to be transparent in the way that the podcast is. We’re writing a monologue about jokes that are McRib, which means that “They’re back.” So like, doing a Borat voice and saying “my wife” used to be really funny and then it wasn’t funny, it was like a wasteland, but these jokes have a half-life, the radiation wears off, and all of a sudden, saying “my wife” is funny again for many reasons.
So, in the joke, we wrote “So, my wife is back.” And then I said, “Not my wife, she’s still with a small Italian man.” It wasn’t so much that my own joke was funny, it’s that Adam, one of our writers, laughed so hard in that sort of church-y way where he wasn’t sure if he was allowed to laugh at the idea of a small Italian man fucking my ex-wife.
I don’t know if he knew it was allowed. It was this weird boss dynamic. I made a joke, but it’s at my own expense, and it’s about something very personal, but he was red and tears were coming down his face, and then I started laughing at how hard he was laughing and that just became that.
That’s a perfectly good ending and I should stop it there. But it reminds me of something I wanted to ask earlier. What’s it like going from being a standup, where it’s just you and you’re your own boss, to being in charge of a bunch of creative people?
Mostly my job is just piping up and saying “yes” or “no.” In fact, Charlie Rose asked Letterman what hosting a late night show was, and he said it’s mostly “yes” and “no.” So I just have to like, trust my instincts and be honest. I think the show is helping me be more decisive in real time. And also, most of my efforts go to trying to be like, as silly as this sounds, “I love you guys, I love your ideas.”
I’m not some guy that’s here to rule over the writers. I’m the relief guy. They have something and they’re not sure if it’s right for the show or not, I get to tell them. They can either keep thinking about it or stop thinking about it, but either way, hopefully when they see my face they go, “Good. Pete’s here for 20 minutes. Let’s pitch him this thing and either he’ll like it or he’ll not, and either way we’ll get an answer. Because unlike TBS, I don’t make them wait a year-and-a-half.
Photography by Kyle Mizono