Pete Holmes is hardly an unknown â 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 heâs 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 OâBrien 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?
Iâll be honest with you, I have a very good idea of what itâll 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 itâs gonna be like, because I think once it gets on its feet and weâre 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 weâre aiming for, which is that I really want to do a late night show that does more sketches. Itâs a little more Chappelle-y. Stuff like the Batman videos that weâve been doing for CollegeHumor, which of course were part of the reason we probably got the show. Everything weâve done for FrontPageFilms.com, all the simple premisey stuff that I do with Matt McCarthy, very lean and simple. Weâd really love to see if we can incorporate as much of that into the show for no particular reason. Thereâs no doctor in the news, weâre just gonna do a doctor sketch because itâs funny.
And when it comes to like the monologue, Iâd like it to be a little less setup-punch and a little bit more maybeâand this is all speculation by the way, I donât even know what weâre gonna end up doingâbut 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, âThis guy stuck his elbow in a garbage disposal. And uh, thereâs goes tennis!â Then you move on. Iâd 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. Weâre gonna see how long we can get away with not even being that topical. But again, I feel like thatâs something someone who hasnât 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. Itâs going to be a friendly, light-hearted tree house vibe, like a silly safe place. But merging it with a the stuff that Iâve 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, Iâd 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.
Itâs going to be a half hour, right?
Yeah. And actually by virtue of being 30 minutes, itâs 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. Youâre just mainlining the absolute best stuff. Hopefully thereâs gonna be no lulls. We donât 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. Weâre 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 itâs 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 weâll 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 reallyâof 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 heâs 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 whoâs 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 weâre 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 thatâs gonna be an asset for us, because I want it to have that feeling of, not only is it me as a performer, but youâre kind of learning everything about me, including my friends and my favorite performers and all that sort of stuff. I think itâll 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 â 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 Iâve come to hosting like a talk show directly. Theyâre so much fun, and some of the segments that we doâlike 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 youâll shoot for one of those interviews. I didnât 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, thatâs been wonderful practice and something that Iâm really grateful for. Hopefully the podcast in generalâwhen I started, I didnât know if I was really able to interview people, and then over the past year, Iâve figured out the way that I interview people. Iâm not even gonna say that Iâm a good interviewer necessarily, but Iâve figured out how I do it, and the way that itâs successful for me. And doing the live episodes has certainly been a lot more one-for-one helpful to doing the show.
And youâre going to keep doing the podcast once the show starts?
Iâm glad you asked that, because I donât know how to address that in a large medium. First of all, the showâs 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 peopleâand Iâm grateful for thisâa 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. Itâs not just fans that would miss it if it were gone, it would be me, because thereâs 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 theyâre 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 naturalâŚ
[Laughs] You know, one of my podcast heroes is Todd Glass. Itâs just likeâI get very lofty when I talk about comedy, so youâll just have to forgive meâbut there is an honoring of when the episode is done. You get it; when itâs done itâs 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. Iâm not gonna push it to get two and a half hours, and Iâm not gonna reign it in to keep it to 60 minutes. You just talk, and when youâre feeling like youâve 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 weâre done. So when Matt McCarthy came on, and heâs one of my best friends and Iâve known him for years and weâve done all this work together, we just kept talking. I just want the episode to be as long as the episodeâs supposed to be. And thatâs what Iâm gonna say thatâs a little pretentious, but I really think, whatever the craft is, itâs our responsibility as the people creating the craft to honor it and let it be as long or as short as itâs supposed to be. Who says itâs supposed to be an hour? Thatâs 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 itâs tiring. I canât do two episodes in a day, and a lot of podcasters can do that, and thatâs something that Iâm 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 Iâm usually done for the rest of the day. I donât know what Iâm gonna do when I have a girlfriend who wants to talk to me after the show. Iâll just have to write a letter ahead of time.
Or a TV show to record.
Or a TV show to record. Thatâs why, the way I see it happening is weâd 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 Iâll just write a little note to myself and be like, thatâs something I keep saying and keep thinking about. I should try doing that in standup. My executive producer, Nick Bernstein, whoâs doing this talk show with me, is always listening to the podcast and heâs like, thatâs a bit. Thatâs something we can do on the show; seeing it in ways that I donât 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 itâs 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, thatâs a good question. I think itâs gonna have to be a merging of the two. My stand-up persona is really me, itâs not a characterâI really am pretty excited. I donât know. I think that guy, plus the podcast guy whoâs 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 youâre familiar with my podcast, itâll probably be a little bit more high energy than that, probably closer to what the live podcasts are like. And then, if youâre familiar with my standup, it might be just a smidge less than that. Just to keep it palatable so itâs not like weâre 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, Conanâs standup booker] and TBS are being. They were like, âWell we think weâre gonna be doing this. Why donât 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?â I was like, âThis is incredible, yeah.â And it made a big difference. It made me so much more comfortable. And I think my wardrobe got nicer as we went, because Iâve never really worn a sport coat or a jacket on stage, and I think the first one I wasnât and in the second one I was trying it out. Because I think people are gonna be like, âYouâre a little boy, you shouldnât be wearing that jacket.â 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.
Whatâs 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 Iâm 30, because he was the only one that I watched. I watched Conan every night. And then, so I was 31âI 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 hereâs 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. Iâm glad that I didnât 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 heâs a hero of mine, that weâre 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 myâthat wasnât even on my mind. It wasnât the last thing on my mind, it wasnât 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 Iâve been in LA for awhile now, youâre used to having meetings and nothing much happens from them. Thatâs just how it is. Your agents and managers will send out for a lot of meetings and you learn to not expect anything. Youâre just aware that youâre slowly contributing to this idea of you being a person thatâs 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, âHello, Iâm a person that maybe you should know about. Later.â [Laughs] So I meet with Conan, and honestly even with that, I was just kind of like, âWho knows, itâs gonna be a thrill to sit down with him. Itâs gonna be a thrill to talk to him. I canât believe Iâm going to his office.â I still have the drive-on pass on my wall from when I went to the lot, because it was a big thing. I wonât 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 didnât 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 Iâm 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, weâre 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 weâre going by and weâre all discussing it.
I wish there was footage of my face the meeting I was in when Conan said, âWell, weâre gonna go into TBS and tell them that the host is really important and that we found our host.â Because thatâs when I found out. [Laughs] Do you understand? You donât get like a golden ticket in your chocolate bar, you find out in a meeting. And then, I believe Conan even made a joke. Heâs like, âAnd we found our guy. Or anyone else.â [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 Iâve 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. âMaybe weâll do this, maybe if this comes up weâll tell this story.â 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 quicklyâall of this happened very, very quicklyâthat 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, hereâs the thing. Itâs all Conan. Conan is the greatest, and Iâd 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; itâs just incredible. Conanâitâs my understanding, so this isnât him talking, this is me thinking out loud right nowâcould 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, thatâs 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 Deonâs 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 Iâm saying? Thatâs me speculating, that sounds like something Conan would do, and I think that might be what heâs doing.
Iâd like to think that weâre creating a little bit of a comedy clubhouse on this network, that these shows will foster and support each other. Thereâll be some synergy there. Itâll make sense when my show follows Conanâs show, and itâll make sense when Deonâs on before. So that kind of older school ideaâletâs have this be a thing where if you like Conan, hopefully youâll like this.
Pete Holmesâs 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. Heâs on Twitter at @PeteHolmez.
Elise Czajkowski is a freelance journalist in New York City. Sometimes she drinks and tweets.
Photo credit: Scott Garrison