Pete Holmes is hardly an unknown — he hosts the hugely popular podcast You Made It Weird, recorded his own Comedy Central Presents, and of course, voices the E-Trade Baby. But he’s officially moved to the next level; it was announced last week that his late night talk show (originally called The Midnight Show with Pete Holmes) will premiere after Conan this fall, executive produced by Conan O’Brien and Jeff Ross. Earlier this week, I got the chance to chat with him about putting together a half hour talk show, working with Conan, and creating a comedy clubhouse at TBS.
What can you tell us about what the show will be like?
I’ll be honest with you, I have a very good idea of what it’ll be like. Having shot three pilots, we have given it a little bit of a test drive. But I also want to be careful to not sound too much like I know what it’s gonna be like, because I think once it gets on its feet and we’re in the trenches of doing a show four times a week, the show is going to inevitably evolve and change. I can tell you what we’re aiming for, which is that I really want to do a late night show that does more sketches. It’s a little more Chappelle-y. Stuff like the Batman videos that we’ve been doing for CollegeHumor, which of course were part of the reason we probably got the show. Everything we’ve done for FrontPageFilms.com, all the simple premisey stuff that I do with Matt McCarthy, very lean and simple. We’d really love to see if we can incorporate as much of that into the show for no particular reason. There’s no doctor in the news, we’re just gonna do a doctor sketch because it’s funny.
And when it comes to like the monologue, I’d like it to be a little less setup-punch and a little bit more maybe—and this is all speculation by the way, I don’t even know what we’re gonna end up doing—but I would like it to be a little closer to my voice as a standup, which is a little bit sillier. Staying on a topic a little bit longer than just, “This guy stuck his elbow in a garbage disposal. And uh, there’s goes tennis!” Then you move on. I’d like to talk about the man with the elbow in the garbage disposal for a couple minutes, and maybe deviate, go to random things and less known stories. We’re gonna see how long we can get away with not even being that topical. But again, I feel like that’s something someone who hasn’t had to make a show four times a week would say. [Laughs]
The short answer, the sound bite answer, is we would like it to be similar to the sensibility of Conan. It’s going to be a friendly, light-hearted tree house vibe, like a silly safe place. But merging it with a the stuff that I’ve been doing for the past decade, which is, my style of standup, my style of sketch, and then my style of interview. So when we do the interview at the end, even though its not gonna be three hours, which my podcast can be, I’d like to see you how, for lack of a better word, weird we can make it in six minutes. I want to encourage the guests to ruin the show or not take it serious or whatever. To see what we can do to kind of breath new life into the interview format for that third act of the show.
It’s going to be a half hour, right?
Yeah. And actually by virtue of being 30 minutes, it’s gonna inform the pace of the show, of course, but I think it will inform the feel of the show a lot too. Even in just doing the pilots, we shot so much more material than we were able to use. You’re just mainlining the absolute best stuff. Hopefully there’s gonna be no lulls. We don’t have the luxury of the hour, so we just have to cram in as much as we can.
So will it be structured more like a Colbert or Daily Show, with one interview at the end?
Yeah, the third act. The Daily Show is a great model for us. We’re gonna allot about the same amount of time for the interview. Something that they anticipate us doing is allowing the spillover of the interview to be available online. I want the show to have a very big online presence; it would be stupid for us not to. So if it’s the long cut of a sketch or the 30-minute version of the interview, that goes online. I know The Daily Show does that from time to time, and I definitely want to be open to that. And then we’ll edit the six-minute best part of the interview seamlessly into the end of the show.
You mentioned you shot three different pilots?
Yup, we shot three pilots. I got to tell you, Conan has been really—of course hugely influential, and as someone who understands what it takes to get a show like this on its feet, he was very incubating and nurturing. When we pitched it, Conan was very clear that he wanted to do more than one pilot, because he’s been doing this almost 20 years, and knows that these shows need time to find their voice. So we shot three instead of one. I know that was very helpful for me, somebody who’s used to talking to somebody for hours and not having an audience there. I definitely benefited from doing three live interviews in the studio, three kind of stand-upy portions, and then the in-studio bits and all that.
On the pilot, you had people like Nick Offerman, Joel McHale, Bill Burr. Do you expect to have that many comedians on the show when it airs, or were you just having friends on for the pilot?
Yeah, I would love this show to be like a clubhouse for the comedians that I love to drop in, the way that Rickles would come by The Tonight Show. That feel of it just being this place in Los Angeles, where so many of hilarious friends live, that they can pop in and do quick things. I mean, do I want to have Ryan Gosling on? Yeah. [Laughs] I do. I would like to have musicians and actors and all that sort of stuff.
I anticipate our bread and butter, especially since we’re gonna be such a small fish in this big pond, will be a lot of my friends and these local guys that I love so much. That may sound like a handicap; I think that’s gonna be an asset for us, because I want it to have that feeling of, not only is it me as a performer, but you’re kind of learning everything about me, including my friends and my favorite performers and all that sort of stuff. I think it’ll be fun, having these maybe lesser-known comedians on as opposed to having the same guests as everybody else.
Listening to the most recent live episode of the podcast from Vancouver, that format feels more like a talk show – bringing multiple guests on for shorter segments in front of an audience. Do you think doing those live episodes has helped prepare you?
Yeah, absolutely. One of the things I love about doing the podcast is doing the live episodes. That is as close as I’ve come to hosting like a talk show directly. They’re so much fun, and some of the segments that we do—like in the pilot, we did fake GameFly ads. It was a little bit different for TV because we have the visual element. We had the amazing Conan graphics people drop the fake boxes for the fake games, so it was very similar to a live You Made It Weird.
And then doing those interviews, knowing that you only have 10 minutes or whatever, which is typically what you’ll shoot for one of those interviews. I didn’t know that, by the way, they edit those interviews. [Laughs] Of course they do, but I never considered that. I was just like, how do they always do it so perfect? But yeah, that’s been wonderful practice and something that I’m really grateful for. Hopefully the podcast in general—when I started, I didn’t know if I was really able to interview people, and then over the past year, I’ve figured out the way that I interview people. I’m not even gonna say that I’m a good interviewer necessarily, but I’ve figured out how I do it, and the way that it’s successful for me. And doing the live episodes has certainly been a lot more one-for-one helpful to doing the show.
And you’re going to keep doing the podcast once the show starts?
I’m glad you asked that, because I don’t know how to address that in a large medium. First of all, the show’s not got gonna be on until the fall, so we have quite a while of completely uninterrupted podcasting between now and then. And then I will say that, because the podcast is just so very much its own thing, my hope and my intention is to continue to do it. Because a lot of people—and I’m grateful for this—a lot of people say they get a lot out of the podcast, and the truth is, I get a lot out of the podcast as well. It’s not just fans that would miss it if it were gone, it would be me, because there’s just no television version of having a really really long, sometimes filthy, too personal, over-sharing conversation with somebody. So I want to keep doing it, the plan is to keep doing it. I understand why people might be concerned that it might not be possible with the schedule. Maybe if we drop down to once a week, that could be some sort of compromise or whatever. But the plan is to keep doing it as much as we can.
I was reading back to your interview from last year, where you talked about how the podcasts were normally 90 minutes and sometimes two hours, and now they’re regularly two and half hours, sometimes three. Do you think, left to your own devices, it would just get longer or longer, or is there a natural…
[Laughs] You know, one of my podcast heroes is Todd Glass. It’s just like—I get very lofty when I talk about comedy, so you’ll just have to forgive me—but there is an honoring of when the episode is done. You get it; when it’s done it’s done. Like, Jen Kirkman just did it, and it was one of my favorite episodes. I loved it, but we were done at two hours. I’m not gonna push it to get two and a half hours, and I’m not gonna reign it in to keep it to 60 minutes. You just talk, and when you’re feeling like you’ve covered everything. There is an organic quality to it.
The whole beauty of podcasts is that there are not people ticking boxes or looking over your shoulder, so we can just go until we’re done. So when Matt McCarthy came on, and he’s one of my best friends and I’ve known him for years and we’ve done all this work together, we just kept talking. I just want the episode to be as long as the episode’s supposed to be. And that’s what I’m gonna say that’s a little pretentious, but I really think, whatever the craft is, it’s our responsibility as the people creating the craft to honor it and let it be as long or as short as it’s supposed to be. Who says it’s supposed to be an hour? That’s stupid. [Laughs] My favorite WTFs are the long ones, like Louis [C.K.] and I believe his Conan episode was really long.
I get why it’s tiring. I can’t do two episodes in a day, and a lot of podcasters can do that, and that’s something that I’m jealous of. In fact if I have a podcast, I try not to talk to too many people that day. [Laughs] Like, I only have so much to give, and afterwards I’m usually done for the rest of the day. I don’t know what I’m gonna do when I have a girlfriend who wants to talk to me after the show. I’ll just have to write a letter ahead of time.
Or a TV show to record.
Or a TV show to record. That’s why, the way I see it happening is we’d record it on Sundays. But the truth is, so much of my material these days comes from things I say on the podcast. I often write down things the guests are saying as things to talk about, or I’ll just write a little note to myself and be like, that’s something I keep saying and keep thinking about. I should try doing that in standup. My executive producer, Nick Bernstein, who’s doing this talk show with me, is always listening to the podcast and he’s like, that’s a bit. That’s something we can do on the show; seeing it in ways that I don’t even see. Everything informs everything, you know what I mean? The talk show will inform the podcast, and the podcast will inform the talk show, just in the same way that the podcast informs my standup and my standup informs the sketches we write and the sketches we perform. So it’s all comedy.
Having seen you live, I would say your on-stage persona is so much more energetic than you are, say, on the podcast. If people know you from one or the other, what are they more likely to see on television?
Yeah, that’s a good question. I think it’s gonna have to be a merging of the two. My stand-up persona is really me, it’s not a character—I really am pretty excited. I don’t know. I think that guy, plus the podcast guy who’s a little bit more accessible, I can see somewhere in between those two things being the thing that hosts a show. Because you have to have somewhere to go. There needs to be some sort of crescendo; there needs to be a build where you have somewhere to go with your energy. So I think the answer is, if you’re familiar with my podcast, it’ll probably be a little bit more high energy than that, probably closer to what the live podcasts are like. And then, if you’re familiar with my standup, it might be just a smidge less than that. Just to keep it palatable so it’s not like we’re not flooring it for 30 minutes every day.
And your relationship with Conan started when you did a spot on his show, right? And then you did the web series and then started working on your show?
Yes. I think we started doing the web series even after we knew we were gonna be doing the pilot, way way way before it was picked up. But that was just another just wonderful indication of how nurturing Conan and J.P. [Buck, Conan’s standup booker] and TBS are being. They were like, “Well we think we’re gonna be doing this. Why don’t we let you host this web show just so you can be on that stage and see what its like bringing up comedians and interviewing them?” I was like, “This is incredible, yeah.” And it made a big difference. It made me so much more comfortable. And I think my wardrobe got nicer as we went, because I’ve never really worn a sport coat or a jacket on stage, and I think the first one I wasn’t and in the second one I was trying it out. Because I think people are gonna be like, “You’re a little boy, you shouldn’t be wearing that jacket.” But then we got away with that, and then it just made it all the more natural when we taped the pilot on that same stage.
What’s your relationship with Conan like?
Conan is and has always been a personal hero of mine. I just love him professionally and his body of work is a huge inspiration to me. So when I was doing standup, my goal was always to do Conan. When I was about 21, I was like, I would like to do Conan by the time I’m 30, because he was the only one that I watched. I watched Conan every night. And then, so I was 31—I always blame my divorce on throwing my plan off for one year. [Laughs] It just swallowed up enough time to make me 31 instead of 30 when I did Conan for the first time.
And here’s the truth, if comedians considered everything that would happen, potentially, when you did a late night spot, you would go crazy and you would never be able to do your job, which is to do six minutes of standup. I’m glad that I didn’t even consider that they might be looking at standups to appear on the show as potential follow-ups to his program. That would just be way too much pressure. I was just there to go out and do my act. So I did it the first time, and then I think it was less than a year later I did it again. The first time Conan was very nice, but Conan IS very nice, so it was hard for me to feel extra special or anything. I just remember he came out and we talked for a couple minutes. I got to tell him that he’s a hero of mine, that we’re both from Massachusetts, and he said good job and then he left, and I walked on a cloud for a couple months. And then I did it again, and the second time was even more fun, I thought.
And little did I know, at that time, the producers Jeff Ross and Conan and TBS in general were kind of wondering who might fill this slot. That was the last thing on my—that wasn’t even on my mind. It wasn’t the last thing on my mind, it wasn’t on my mind at all. So then out of the blue, I got a call to meet with Jeff Ross, and then Conan. And honestly, the way that show business is, and I’ve been in LA for awhile now, you’re used to having meetings and nothing much happens from them. That’s just how it is. Your agents and managers will send out for a lot of meetings and you learn to not expect anything. You’re just aware that you’re slowly contributing to this idea of you being a person that’s in show business, and you kind of maintain awareness by taking all these random meetings. Young comedians, I always tell them that the first 150 meetings you take will lead to nothing, and their only purpose to is to be like, “Hello, I’m a person that maybe you should know about. Later.” [Laughs] So I meet with Conan, and honestly even with that, I was just kind of like, “Who knows, it’s gonna be a thrill to sit down with him. It’s gonna be a thrill to talk to him. I can’t believe I’m going to his office.” I still have the drive-on pass on my wall from when I went to the lot, because it was a big thing. I won’t play it cool, it was a big deal.
And I go into the meeting and we started talking. Basically, we did a mini-episode of You Made It Weird. We didn’t really talk about God, but we talked about comedy for a very long time and at the end, we just pinned it on at the end, a minor discussion about talk shows and hosts and him thinking that I could be a good host. And so, that blows my mind, but I’m still kind of like, who knows what that means? That could be never, or that could be in a year, or that could be whenever. Next thing I know, we’re meeting again and again and again and again, and I started going in regularly and Nick Bernstein is involved with me at this point, and now we’re going by and we’re all discussing it.
I wish there was footage of my face the meeting I was in when Conan said, “Well, we’re gonna go into TBS and tell them that the host is really important and that we found our host.” Because that’s when I found out. [Laughs] Do you understand? You don’t get like a golden ticket in your chocolate bar, you find out in a meeting. And then, I believe Conan even made a joke. He’s like, “And we found our guy. Or anyone else.” [Laughs]
And then from there, Nick Bernstein and I worked really hard on preparing the pitch. Conan and I discussed the pitch and the strategy, and I saw Conan not as what I’ve always seen him as, which is this kind of infallible icon of television, but I saw him as another one of us, another artist-performer-comedian, because we were discussing how to pitch it and what to say and what not to say. “Maybe we’ll do this, maybe if this comes up we’ll tell this story.” Just like me and countless friends have gone into pitch things before. So we went into TBS, we met with [TBS president] Michael Wright and a couple other people, and we pitched the show, and found out very quickly—all of this happened very, very quickly—that they were gonna let us make [the pilot].
You and Deon Cole, who also has a Conan-produced show on TBS coming out, both started working with Conan after doing standup on his show. It seems like you two might be the new model of what can happen if you do a good set on a late night show.
Well, here’s the thing. It’s all Conan. Conan is the greatest, and I’d really like you to print me saying something along those lines, because every chance I get to express my gratitude to him and my being so impressed by his vision and his understanding of show business; it’s just incredible. Conan—it’s my understanding, so this isn’t him talking, this is me thinking out loud right now—could have gone to other networks when he left The Tonight Show. He pretty much had his choice to maybe get a bigger payday or this or that. Again, this is me just speculating. Going to TBS, and going to a place where I believe he felt like he would be given more of an opportunity to create a real network, to make a real change, to have it really be a network that has a unifying theme, that’s genius on his part, I believe. He went there because TBS understood his sensibility and understood, I think, his vision for the network and for his show, and when I see TBS picking up shows like Deon’s and mine, I see them also being very smart and being hip to this idea that I credit Conan with having, which is that we can create this little family of shows that will make this whole family feel… related. [Laughs] You know what I’m saying? That’s me speculating, that sounds like something Conan would do, and I think that might be what he’s doing.
I’d like to think that we’re creating a little bit of a comedy clubhouse on this network, that these shows will foster and support each other. There’ll be some synergy there. It’ll make sense when my show follows Conan’s show, and it’ll make sense when Deon’s on before. So that kind of older school idea—let’s have this be a thing where if you like Conan, hopefully you’ll like this.
Pete Holmes’s hour-long standup special, Nice Try, The Devil, will premiere on Comedy Central later this year, and his podcast You Made It Weird is on the Nerdist network. He’s on Twitter at @PeteHolmez.
Elise Czajkowski is a freelance journalist in New York City. Sometimes she drinks and tweets.
Photo credit: Scott Garrison