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Comedian and Late-Night Host Pete Holmes Would Like to Thank Conan O'Brien, Scrooge McDuck, and Anyone Else Who's Ever Helped Him with a Joke

He writes, produces, acts in, and hosts his own show—and still has time to draw cartoons for The New Yorker.

Pete Holmes is living proof that great comedy can come from a comedian's sheer lack of irony, at least in terms of how he views his work. Entering season two of The Pete Holmes Show, a variety program airing weeknights at midnight after Conan on TBS, the multi-tasking host is feeling seriously passionate about his craft, so much so that he offers disclaimers that his answers might sound "lofty." But that no-joke grit has gotten the joke-happy Holmes to where he is now, leading a late-night show, hosting the popular podcast You Made It Weird, and even lending his voice to animated series like Ugly Americans and American Dad. Holmes is a long way from his Dead Poets Society-inspired college improv troupe (we'll explain later), yet he seems as enthused about winning over the crowd as an untried comedian.

The 34-year-old recently sat down with DETAILS to chat about airing his dirty laundry, getting intimate with Sears catalogs, and what it feels like to go from being a stand-up comic to having them appear on his own show.

DETAILS: Looking into your background, I stopped at the words "The Sweaty-Toothed Madmen," which was the name of your comedy troupe when you were attending Gordon College in your home state of Massachusetts.

PETE HOLMES: Do you get the reference, by any chance? It's pretty obscure.

DETAILS: I wish I could say I did.

PETE HOLMES: It's okay. I'm never the guy who gets the reference. I've been watching True Detective, and everyone's like, "Did you get this? Did you get that?" And I'm like, "No, but they have guns!" The Sweaty-Toothed Madmen is an improv troupe, and it has that name because, in the movie Dead Poets Society, Ethan Hawke's character doesn't write a poem, and Robin Williams's character makes him go in front of the class and improvise one. And one of things he says is "a sweaty-toothed madman." Gordon College is a Christian college, with Bible classes and stuff, and there was no improv team, so in my sophomore year my friend Dan Buck and I started one. It was really fun, not just because we faced the challenge of having to keep it pretty clean, but because the campus was starved for entertainment. So if you put on a show on a Wednesday night, maybe 150 people would come, which, for me, was a lot. This is when I started to believe in myself, and wanted to do comedy full time.

DETAILS: These days you wear a lot of hats: writer, producer, voice actor, host. Was there ever a point when you thought, "Maybe I'll just work behind the scenes and won't put myself front-and-center, or on camera"?

PETE HOLMES: This is gonna sound a little lofty, but you need to do what's appropriate—you need to respect the joke, or the idea. Sometimes a joke is better for you to write and give to somebody else, sometimes it's better for you to be in it. Sometimes it's better for you to make it a cartoon and use your voice. I have a unique opportunity with The Pete Holmes Show in that I'm in almost everything. We have some things that aren't quite right for me, and we take advantage of that when we can change the tone or the feel, but for the most part I'm writing it, I'm acting in it, I'm involved with the edit, and I'm introducing the segments as well. So, I guess, to answer your question, I enjoy doing many types of comedy, as long as it's funny.

DETAILS: The show's first season launched last October, but even before then, with your podcast and other ventures, you were chatting with so many colleagues, from Dave Coulier to Demetri Martin. Is there ever a sense of competition in these scenarios with these comedians—a need to out-funny one another?

PETE HOLMES: There's some competition, but most of the successful comedians I know are pretty competitive with themselves. In conversations, I think it's more of a joining-forces thing, and, for me, the best episodes of my podcast are [ones in which] we really do merge and find what we can do together.

DETAILS: I was going to ask some details about your past, like losing your virginity at 21, marrying young at 22, and divorcing six years later, but then I watched the Allison Williams segment of your show, and she gave me all my answers. Is there anything that's off-limits on You Made It Weird?

PETE HOLMES: I've edited some stuff out when I've crossed the line, but, for the most part we leave it in. That's been the great experience of [the podcast] and the TV show—we're trying to see what happens when we show the full person. What if you know when I lost my virginity? Or when my wife cheated on me? One thing that came out of a podcast was weird things that we've masturbated to, and I tried to find images from a Sears catalog, because that was the first thing I ever jerked off to. That's the kind of joke that's blue, but it's true! And those are the things that really interest me: What is true, and vulnerable, and weird, and something that we haven't seen before?

DETAILS: Do you think those interests make you stand out among your peers?

PETE HOLMES: I do think some of the jokes are ones that my contemporaries would never make. Another part of our goal with the show is, "What if the host isn't a TV personality as much as a guy who's really uploading the entirety of his personality, including some of the darkness and strangeness?" We're trying to allow the audience to engage with that, as opposed to summarizing what's happening in current events and pop culture, or interviewing a celebrity about a movie. I'm not putting down late-night; I love late night. I'm just trying to so something a little bit different.

DETAILS: Conan O'Brien is a producer of your show. I don't think I've ever asked someone who knows Conan what he's like, so I'm going to ask you. Is he a mad genius, or just really good at playing one on TV?

PETE HOLMES: He's a monster. [Laughs] No, he's incredible. He's so hands-on and involved in the show. When we did our first taping [for the new season] he was there watching like a good dad who goes to little league games. He's a big believer in the process and he know it takes time for a show to find its legs. As a person, he never stops moving. He loves being around people; he absorbs their energy. And he's the most naturally funny person I've ever known. I've never seen him "off." He's kind of a hurricane.

DETAILS: You mentioned getting to do a lot of different things now that you have your own show. In December Gabe Liedman became your first stand-up guest. What's it like to come up in stand-up and then have a stand-up comic on your own show? It must feel very full circle-ish.

PETE HOLMES: That really solidified the whole thing. When Gabe came on I got to give the speech to the audience that I always wanted someone to give for me before I did a show, which was like, "Hey, there's going to be another guy out here! Please laugh at everything he says!" Gabe doesn't need that help, but you're right to notice that. It was very, very surreal.

DETAILS: What can we expect in the show's new season?

PETE HOLMES: We're going to be doing a lot more stand-up, and we're also going to do that old Tonight Show thing where we have a comedian on and then chat with them afterwards. I think it'll break down to one stand-up a week, which is fantastic. There are so many great people we're going to be bringing on the show—people who I honestly can't believe haven't been on late-night yet. And you mentioned Allison Williams—that was one of our most popular interviews, and it was done without a live audience. We're doing more interviews like that because it can afford you that luxury of getting into something a little bit deeper, then also have jokes that are more like those that unfold between two friends. Other than that, there'll be a lot more sketch—Street Fighter parodies, a Sherlock parody, maybe even a True Detective parody.

DETAILS: With guns.

PETE HOLMES: With guns! Right.

DETAILS: Yet another thing you have hands in is visual art, and I understand your work as a cartoonist has appeared in The New Yorker. If you were to draw an illustration of your life right now, what objects would you include in it?

PETE HOLMES: [Laughs] My god, how to draw extreme gratitude? The first thing that came to my mind is some sort of Scrooge McDuck scenario where I'm jumping into gold coins, but they're not "money" coins, they're just opportunities of getting to work with your heroes and friends. That's honestly how I feel. It's not a payday joke; it's just that I feel so grateful. I'd basically have to draw myself coming out of a giant present.

• • •


Also on Details.com:
Wise Guy: Seth Meyers
Crossdressing Aussie Comedian Chris Lilley Returns in HBO's Ja'mie: Private School Girl
Late Night Style: The Best and Worst Dressed Talk Show Hosts

Photo courtesy of TBS.
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