Pete Holmes on How the Comedian Became the Modern-Day Philosopher

Photo: Photo by Heather Kennedy/Getty Images for SXSW

Like Marc Maron's “WTF,” Pete Holmes spends a lot of time talking comedy with his peers on his wildly popular “You Made It Weird.” The difference is, Holmes is a great deal more idealistic, quick to compare comedy to a religious experience. I spoke with him for my piece on the new comedy boom, but there was so much good stuff in our conversation, we’re running a full transcript of our conversation here. Holmes discusses what makes this period in comedy different from before, how comedians today are better prepared, and why a comedy show is like church.

So, basic questions first: What is your basic timeline?
It’s a little bit vague because I was doing stand-up in 2000 in college. I consider my start date 2001, but it’s really 2000. Jesus, that’s 15 years. I did it in Boston under five times. Then I moved to Chicago in the summer of 2001. I know this isn’t what the interview is about, but I really contend that 9/11 has a lot to do with why a lot of comedians at my age had a fire under them to get better. Then in 2004, I moved to New York, and I was there until 2010, when I moved to L.A. 

So, the 9/11 point. What I found interesting is when I talked to Kumail Nanjiani, I talked about you Chicago guys, and he talked about how much you guys challenge each other to move forward. Do you think that’s related?
It was the beginning of the alternative scene for us. It was happening in New York certainly before us, and by "alt scene," I really do mean a scene in nontraditional venues where the premium isn’t always on destroying as much [as] it’s on being very authentic and original. Whereas the club scene can bang some much-needed pragmatism into you as a comedian, like how you’re supposed to give the audience an entertaining hour of comedy, but that’s honestly where you get a lot of material about not being able to find the G-spot. There’s nothing really wrong with that — I mean, I didn’t really like it — but we didn’t come up in that scene. Part of why Chicago was a great place to start and what Kumail is talking about [it] is that it was people doing comedy because we were doing comedy. There was no industry, there was nowhere to make it. “Making it” to us was being able to emcee at a club, or maybe, honestly, getting good enough to where you moved to New York or L.A. I wouldn’t say 9/11 was the main thing pulling us together, but it did snap me into my own mortality and made me double down on my dreams and my drive. 

That group just felt ordained, it felt meant to be. It was me, Kumail, T.J. [Miller], Kyle [Kinane], [Matt] Braunger, John Roy, and I’m forgetting people, I always do. It was an absurd amount of really good comedians coming up in a scene that was good at incubating original thought and creativity. It rewarded you for doing something that only you could do, as opposed to just banging it out in the batting cages, which is the scene just down the street at Zanies [an old-school Chicago comedy club]. Not to put down Zanies, but nobody from the Chicago time claims Zanies as their mother. 

Do you think there’s any stylistic overlap with you guys?
Yeah, absolutely. I’ve been very vocal about this, but T.J. Miller is one of the most insanely original comedic voices this generation knows, and I know for a fact that the whole scene ripped him off a little bit. There's those of us that are honest about it, and then there’s those of us that are in denial. At least our crowd work was influenced by the way T.J. improvised, because he was a trained improviser. I was a trained improviser as well. It was his positive slant. The thing I learned from T.J. specifically, and it’s such a huge part of who I am, and it fits so perfectly, is when something happens, you go at a heckler with the approach of, "I love that you blank blank," as opposed to, “Shut up, you’re fucking ruining the show.” So even when I see someone like Cameron Esposito, whom I didn’t come up with when she started in Chicago, I see T.J. And it’s funny because he wasn’t like a huge part of that scene in the way that I wasn’t a part of that scene. We were all open-mic-ers. 

Do you feel like there’s T.J. in Hannibal Buress?
That’s a good point and a great exception to the rule. Hannibal’s amazing, and he really carved his own way. This is not talking out of school, he knows this: Hannibal was a bit of a punch line. This young kid named Hannibal would go up, and he wouldn’t do very well. But he didn’t stop. He did every show. He’d find a way to do a set on a poetry slam. But I still remember the day that Kumail called me. I was living in New York, he was living in Chicago still, and he said, “You’re not going to believe this, but Hannibal’s funny now.” So he went from being somewhat forgettable to becoming this undeniable hilarious guy in a couple years. Hannibal, I swear to God, had a machete and was hacking his own way. T.J. and Hannibal are similar in that way, and you have to understand, I consider myself an authentic and creative original person, but then there’s that next level up where you’re like, These motherfuckers are getting it from somewhere unseen. 

What has having an improv background meant for this generation of comedians? In previous times, there was almost this divide.
I remember having a very formative discussion with T.J., and we were like, “I don’t understand why you wouldn’t do everything funny,” and the disappointment that we felt specifically when we’d find out people like Ben Stiller never did stand-up. He’s a comedian and a writer and performer, why wouldn't he do stand-up? That's why I like doing stand-up like improv, by looking at the audience as your scene partner. It's something that’s very difficult for a guy just banging out jokes to ever understand. You have the Catholicism of stand-up, the rigor and the ritual, and then you have the Unitarianism of improv, and I really think you need to step into both pools, even if ultimately all you’re going to do is be a stand-up who respects the intelligence of his audience, listens to the types of laughter and information and feedback you’re getting in every second. 

I talked to Marc Maron earlier in the week, and he was talking about how there were a lot of amateur comedians today that think they’re comedians because they do three indie shows a week, but they never get paid.
I don’t know how helpful or unhelpful a perspective like Maron's is. He’s a little bit more old-school in the sense that you need to put "comedian" on your W-2. I am much more of the thought [that] you would be much better if you live in Portland — there’s a nice little scene there. Don’t go on the road and try to bang out 50 bucks just so you can tell your dad at Christmas that you’re a comedian. (He’s an alcoholic; he doesn’t give a fuck anyway.) That’s what Kumail, T.J., and I and all these guys did. We weren’t satellite-ing the scene, but we also weren’t making a living. I was a waiter, Kumail worked a tech job. T.J. did promotional work for Coors Light or something. I understand there might be some bitterness because there’s a clubhouse feeling where we don’t want to include you in this special thing if you’re not doing it seriously. It’s like the mafia. We want you to take an oath, we want you to swear off a straight job. We want you to sacrifice your relationships and your family to do this thing of ours. And if you’re going out on a couple of robberies but you don’t ever do any serious hit-jobs, we don’t want you to be able to call yourself a gangster. 

What's your explanation for why right now it feels like comedy is at a boom or a peak of some sort?
It’s communication. I’ve always said, if Bill Hicks had a podcast, Bill Hicks would have been more than just comedians' favorite comedian, he would have been able to find the pockets in every city, the couple thousand people in every major city that would sell out big stadiums for him. But he didn’t have Twitter, he didn’t have podcasts, he didn’t have YouTube, so he couldn’t send out his frequency to the people that were dying to hear it. I remember Eugene Mirman would go on tour, and he’s always been very web-savvy. Eugene is one of the weirdest acts you can find; he’s a strange bird. He’s hilarious, but I was like, “What the fuck are you going to do in Iowa City, you're such an East Village comedian." And he said, "There’s an East Village everywhere." The difference between Eugene and Bill Hicks is that now you don’t just pop into people’s lives twice a year on late-night, if they even watched it. You can have a daily relationship with fans. My touring certainly bloomed for me because of the podcast. It’s not some comedian who’s at some comedy club telling some joke. It’s our friend Pete, whom we know everything about and we care about and we know we like his sense of humor and he knows our sense of humor. We’re going to go because we want to support him because we know what we’re going to see. 

There’s a sophistication that wasn’t there back [in the] Evening of the Improv [days]. They know what a bit is, they know that you’re working it out, they know that they’re involved in the process. If they laugh, maybe you’ll riff, maybe this will become a thing that becomes the finished piece that we all get to enjoy. So, the audience has identified themselves as the guitar to the musician. They’re not just sitting there to get fucked up and smoke a cigarette inside, which is what it was in the ’80s, they’re there to actually participate in something that, as lofty as it sounds, it's communal. 

Do you remember when you first heard the term comedy nerd, and what you thought of it?
Yeah, that’s a good question. It was probably in New York, so it was in between 2004 and 2010. I do remember hearing it, and I do remember just getting it immediately and being like, “Oh, that's perfect.” As soon as I heard the term comedy nerd, I’d hoped there was a lot of them. 

Why do you think comedians were particularly good for this new media landscape, with Twitter, podcasting, YouTube?
As T.J. says, comedians are the modern-day philosophers. And not too many comedians would like to say that because it makes them sound like lofty assholes, but the truth is, my job is [to] look at everything that’s happening inside and outside of me, and then articulate that. You could say there hasn't been a comedy boom and there’s just more entertainment and more ways to get it, but also there is something culturally lacking. There’s something spiritually lacking, for lack of a better term. And that doesn’t have to be mystical. It’s a lack of connection and community that we used to get from things like churches. It’s more than just entertainment. We're looking for insight. We raise some people up and [are] like, "Louis [C.K.], he talks the truth about parenting and divorce." And he's become an authority in an authorityless society. We all have maps and Google, and we all have ways to get to fucking Nevada on a Southwest flight, but the thing that we can’t all do for ourselves or get from our phones or get from just reading something on the internet is perspective and authenticity and a direct, soulful communication with somebody. 

It’s certainly necessary, but especially if society, which I think we are in, is isolated and lonely and afraid and desperate. You have these churchlike experiences, where groups of people go to live shows together to merge and to bond as one thing called an audience, and then that audience merges with the thing called the comedian, and it’s something that we call a show. Time slows down a little bit.

Talking about your podcast, do you remember when you realized its effect on your audience?
Yes, certainly. I remember people always used to say that it would help your road sales, and I was like, “Who cares about road sales? I don't want to do road,” but that was because I’d never done the road where every single person knows they’re there to see you. That’s not the road, that’s touring. I’d do a show, and the first time you see a homemade T-shirt or somebody brings you a vegan muffin or something, you’re just like, "Oh, these people know me and they like me and they get me." You start to see this shorthand where you don’t have to introduce yourself to the audience. You just get to go up and continue a conversation already in progress. When you see a friend, you don’t have to go, like, "Just to remind you, we went to high school together and I like chocolate." You can just pick up where you left off. 

So, I wanted to talk a little bit about the TV show [The Pete Holmes Show]. I heard you talk about it right after it was canceled, but at this point, it’s been some time. Looking back, what is your feeling about doing it and then it being canceled and now it being a thing that you don’t do? 
Yeah, I remain very grateful that we got to do 80 episodes. I don't know that if we had continued under the circumstances that we were working in, meaning a very, very, very small budget, if we could have maintained the level of quality that we all wanted to get. So, I’m like, “Okay. That’s an okay place to stop.” Ideally, it could have kept going, and ideally, we would have had a bigger audience, and that would mean more money, but it changed my life all for the better. It became a thing where you could get a good meeting or you could get a good pitch. When you had an audition or meeting with the network, they know who you are and what you do and what kind of stuff you do and what kind of parts you’re right for and what your voice is. So much of stand-up is trying to bang out the idea of this is who I am. This is who I am! This is who I am! So, when you have a national platform to really give people a crash course, even if you only see ten episodes, even if you only see five, you’ll have a decent idea of who I am and what I do. I remain incredibly grateful for that. 

I will say, I just did a test show for The Late, Late Show, and it was bad. It brought up a lot of repressed sadness. I was like, “Oh, I liked doing that.” And then on top of that, “Oh, I have the skill set that very few people have.” James Corden is one of them. He’s fantastic. But I am one of those people that can do this and was good at it, and it kind of breaks my heart to be, like, chosen and selected and celebrated, and then kicked out of the party. So, it hurts. It does make me sad. But you can’t be sad for long. You’re just like, "Okay, what’s the next thing?" I’ll feel better when I know what the next thing is. That's for sure. 

You have some peers that also had their first big shot that didn’t necessarily work out. Do you think you and your peers and this generation are less worried about their breaks not working out? Are they more careerist?
Yeah. We’re the musicians that watched Behind the Music, to quote Bill Burr. He has a great bit about that. It’s like, don’t bands watch Behind the Music? Why do they all keep doing cocaine and heroin and dying and losing all their money? Didn’t you see the MC Hammer one? Like, look at SNL these days. They’re all a bunch of fucking squares with sweaters with the collars popping out and drinking coffee and doing yoga during their break. And I think that’s better. It used to be guys injecting cocaine into their dicks and being like, "What about a shark that knocks on your door?!" But everything’s been cleaned up. 

So, yeah, I had a talk show canceled. Okay, let’s go back to the list of people who had talk shows canceled. Johnny Carson had his first talk show canceled. Jon Stewart. Letterman. Conan O’Brien, if you look at The Tonight Show as a show that got canceled. So there is an understanding and a deeper appreciation of history that I think hasn’t existed before. If you look at someone like Freddie Prinze, such a tragic story in the ’70s: He got the show, gets famous, gets a lot of money, gets a lot of cocaine, and then gets a lot of guns. We don’t seem to do that. You see guys like Ron Funches get on Undateable, and I'm pretty sure Ron Funches is saving his money. I saved my money. I booked an E-Trade commercial. That’s a lucrative gig. I still lived in a fucking shithole apartment in Bushwick because nobody does that anymore. Nobody goes like, "Okay, I’m going to gold-plate my stairs." We do have an understanding that it’s a long game. People do think more abstractly about their careers as a whole. You see people like Roseanne and Gilbert Gottfried and Norm Macdonald and you see how there’s ebbs and flows. Look at Marc Maron: He’s about to kill himself, and then he does a podcast. We know to buckle down. Don’t give up, relax. Sometimes I'm in one of those phases where you wait to hear about several different things. Sometimes your life is just playing Shadow of Mordor and jerking off. And that’s okay. That doesn’t mean you’re not going to work again. 

We know there was an end to the last comedy boom. Do you think of this as a thing with a peak and there’s going to be a drop-off eventually, or do you think there’s something fundamentally different about what is happening now?
I don’t see this as what happened in the ’80s. In the ’80s, you had things like the Improv cashing in and putting out these comedy specials on TV, and then you had a bunch of discotheque closings that had stages and microphones, and all of a sudden, we see a way to turn these discotheques into overnight comedy clubs, and then, of course, the nation was obsessed with it, and they all started going out and seeing it. It became like a happening. Nowadays, I don’t see it that way. Things could certainly cool down, there might be less work than now, but the difference is that in the ’80s, there were guys that were garbage that could make $80,000 a year just because there were so many clubs and so many weekends. It was just this gluttonous self-eating monster. Now I see a lot of comedians that are great. Even young guys that are just starting are better, like, there’s more access to more information — podcasts, specials, YouTube — people are learning and growing quicker. I just had Daniel Sloss on my podcast. I think he’s like [20-something] years old and he’s done seven hour[-long] specials. Granted, it’s not in America, but still, come on. That’s incredible. 

The thing that makes me think it isn’t like the ’80s is that it’s not these gimmicky fucking shitty comedians. It’s people whose heroes are Louis, and then they go and they try and unearth their truth. Their heroes are Maron. They’re heroes are Kumail or T.J. So, it’s not just people trying to be like, "Oh, I can do coke and fuck waitresses and not have a straight job." It’s people going like, "No, I'm really quick to call stand-up an art, I’m really quick to respect my fans and respect the community that I’m a part of."

If you talk to me in ten years and there’s fewer clubs and there’s fewer comedians, that doesn’t really matter. We’re all sharks, and we’re all cowboys. When you start closing clubs, we’re going to sidestep. We’re not fundamentalists. We grow, we move. Like Eminem, "I’m not a rapper, I'm an adaptor." That’s what we’re all doing. If it’s not going to be alternative fucking comic-book comedy shows, it’ll be the next thing, and we’ll be the ones making that funny.