Conner O’Malley, the New King of Weird

At a time when late night shows strive to be either the most incisive source for political coverage or YouTube’s next viral megahit, it’s nice to know we can still depend on writers like Conner O’Malley to bring some genuine weirdness. Since joining the Late Night with Seth Meyers writing staff in 2014, O’Malley has made dozens of appearances as all kinds of bizarre characters, from Trump superfans to Norwegian telepathic black metal guitarist Gørbøn Hausinfrud to The Blacklist: Late Night Edition hero James Splader. On top of all that, he’s released a steady string of hilarious man-on-the street-style videos over the past year, and last month he released his most ambitious video yet: a 23-minute “episode” called 2Nite Show Starring Johnny Carson, in which he stars as the former late night host in what I can only describe as what The Eric Andre Show might look like if it was hosted by a drunk Carson then recorded on a VCR in Chicago in the early ‘90s. I recently spoke with O’Malley about writing for Late Night, how he makes his videos, how 2Nite Show originated, and why he thinks creative limitations are just as important as creative freedom.

You’ve been writing for Late Night with Seth Meyers since it debuted in 2014. What’s it like writing for the show during its first election year?

There’s definitely a lot more stuff to work with. I mean, the show has always been pretty political, so it hasn’t really changed a ton. Also, a lot of the political stuff is written by people on the staff who are smarter and better at that than me – I write the dumb stupid stuff. [laughs] There’s a guy Sal Gentile who writes all the political stuff here, and Jenny Hagel – they write like everything Seth says at the desk.

The “Closer Look” segments have been consistently great.

Yeah, and Sal and Jenny work so hard on those. And I’m busy writing dumb stuff for the crew.

When I was a kid, watching the weird stuff on Conan – the “dumb stuff” – was my favorite thing. And I think in terms of late night today, Late Night really keeps the weirdness alive that Conan and Letterman started.

Totally. And it’s such a great tradition, going back to Letterman, of this time slot being used for the most insane ideas. I think of Conan’s “Tea Copywriter Cagematch” sketch – nowhere else would that exist than a show that’s on this late. Even old Letterman with Chris Elliott stuff and things they were able to do that were just so, so silly and so, so dumb.

There’s been a little crossover between things you make for Late Night and videos you release on your own, like the Trump supporter videos. How do you juggle making things for the show and other videos you release independently?

Well, for the show, it’s usually stuff that would be more expensive to do, like when we went to the robotics fair. I never would’ve been able to do that on my own. And the Trump rally videos are just…there was no way we could’ve done those on Late Night, truly, just because we’d have to get releases from everybody and we’d have to have a big crew. Me and Joe Pera just went down to Orlando and shot all that stuff on cell phones, and it was just me and him, and we self-funded it. And there’s just no way that would’ve been shown on network television. As far as the other Trump remotes we did for Late Night, I remember having a conversation where it was like “We’ve got to get this written and try to do it because he’s gonna drop out soon,” which is insane to think because now he has the nomination.

You’ve been releasing videos pretty steadily since that McDonald’s video last year, which I loved. Can you run me through how one of your videos typically gets made?

Thanks! And yeah. With the McDonald’s one there wasn’t a script or anything like that. I just contacted this guy Joe Avella, who’s a friend of mine from Chicago who lives out here, and he got some buddies and cameras. I ordered a McDonald’s costume off eBay, and we had three guys who went up to the Burger King before me, and I went in and just kind of went off for ten minutes until they kicked me out, and we edited that down to about three minutes. That one came together in the edit. It was the same thing with the Orlando Trump rally – I was like “I really want to go and do something at some conservative rally,” and I told Joe Pera and Tom Hunt, who produces all that stuff, and we just had our eyes out for something like that. So once I saw he was speaking at Orlando I was like “I have that week off, let’s just book tickets and go down there.” And we really didn’t have any idea what we were going to do. We came up with the narrative while we were shooting, and even more so when I sat down and edited it with this guy Marty Schousboe.

But the process is really we go out, we shoot a million different things, and then we kind of figure it out in the edit. But with the Arizona one, we knew that I would go to the Mexican border and try to build a better wall. Each time we’ve done it, we’ve kind of had more and more an idea of what it would be, and we’ve started writing outlines and things like that, but it really was this process of “We just have to start moving on it, and then we’ll figure out how it comes together as we’re doing it.” It was a strange process, and it was really fun afterwards being like “Okay, well let’s drive to SeaWorld” and “Let’s go to Epcot.” We walked around and shot for twelve hours straight, then by the end we were like “Okay we have all this footage – what’s the idea, what’s the narrative?” And then by the time we did the New York one, we kind of had a very clear idea of that would be.

Rewatching your videos – and to go back even further, your old Vines too – reminded me of a story John Hodgman told about Stephen Colbert a few years back. He said he heard that Colbert trained himself to stop feeling embarrassment sort of through immersion therapy, where he’d go out in public and do silly things until it didn’t embarrass him anymore. It was a secondhand story, but it does sound like something Colbert would do.

Yeah. I’ve also read interviews with [Steve] Carell where he talked about doing those Daily Show remotes and how that was really hard for him – he had to get over that too. But when we’re doing those Trump videos or the porn convention thing, there’s so much footage of me being like “Did we get that?!” and me being a shitty piece of shit looking nervous, because I’m also simultaneously producing it and directing it and editing it in my head as we’re doing it and I take on all those fears. So that doesn’t go away, and there’s only seconds of “Okay, I think what just happened is funny, and we know that we definitely got that from both angles and the sound is working.”

And I’m constantly trying to get to a place where I’m not feeling self-conscious. When we shot the New York one and I was going into a Bernie rally with a “Make America Great Again” hat on, it felt like walking through a Holocaust museum with a swastika armband. I felt so self-conscious and so horrible, and that kind of doesn’t go away. But once you get a couple interviews under your belt you get warmed up, and you get to a place where you see something and then you just go after it. And especially with the Vines, there wasn’t ever any master plan behind all those. It was just this incremental improvisation of “We’ll start here. Where can it heighten? Where can it go?” It escalates naturally, and I’m just trying to stay open to that. I want to go where that takes me.

That idea that the self-consciousness never really goes away seems to be really common. Even the most successful people still feel that way, it’s just about how you deal with it or harness it.

Yeah, and it gets lesser and lesser, but it’s like running: How do you run a marathon? To someone who’s only run one mile it’s like “Jesus Christ, that sounds so horrible!” But with slow boring progression – repeating it over and over again – it gets easier. But it can still suck…bad. [laughs] Yeah.

Let’s talk about your newest video, 2Nite Show Starring Johnny Carson. How did it come together?

Well I did a show at the place we shot it at called the Aviv, and everybody was smoking. I used to be a pretty heavy cigarette smoker, and I was like “This is insane to be in a place where you can smoke inside!” It’s such a kind of punk, DIY venue, and the smoking made me think of the days when you could smoke on television on The Tonight Show. I’d been doing a Carson type thing at a couple different shows and I thought it’d be fun to do a whole thing there and film it. So it was kind of the smoking that spurred it on. I was looking to do something a little bit different that would be crazier, and it just lined up where it was a good thing to do.

It has so many funny people in it too. Dan Klein’s Seinfeld promos are so great.

Oh yeah, those are so funny.

Who helped you put it together?

Joe Pera, Tom Hunt, and I have a production company, Chestnut Walnut, that did it. Joe actually ran one of the cameras, Tom directed it and produced it and did the sound and everything like that. A lot of my friends from the Annoyance just moved here from Chicago, and we do a show on Thursdays at 10:30 at the Annoyance called Holy Fuck that’s a free show where people put up bits that are real loose or silly and goofy. All those people had moved to town so I figured it’d be the perfect opportunity to get people like John Reynolds and Devin Bockrath and Gary Richardson and Wes Haney and Andrew Tisher onstage. And Dan was so funny – he did those from LA. But the person who did the most work on it is this guy Andrew Peyton in LA, who’s this editor who found all the footage. We shot a 50-minute long show and he edited it down to just 23 minutes, and he put in so much work and it’s really all him.

He found all the old TV clips and commercials?

Yeah. I really wanted a lot of Bozo stuff in there and local Chicago commercials that I grew up watching, and we wanted it to mimic the idea of what it felt like when your brother had the remote and you were forced to watch what he was watching. And the whole idea of cable and how channel-flipping is gone and how much the landscape has changed, and even connecting that to what the late night talk show used to be and this kind of very recent past. Andrew put in so much work on it.

With Late Night you have a bigger budget but more creative limitations, and with your own videos you have a tiny budget but total freedom. How do you feel about working within those confines or lack thereof?

I mean, I do think that it is great now where you’re able to do whatever you want and put it out, but I do think that creative boundaries really help a lot, especially to figure out your voice. I do feel like you need that, and I’ve definitely benefited tremendously from that. When I was in Chicago, I was on a Harold team and I had to do this longform improv structure that I really hated and really didn’t like – like if I was given the option of not doing it I would’ve never done it. But doing it confined me to this thing, and I learned so much from it. Then when I went off and did my own thing, I was able to harness what I learned from this thing that confined me. But I think that those boundaries are really important – having someone not saying no but being like “Well, maybe it should be more like this” is super helpful and very important, and I often feel like if you stray too far and go off in your own direction, you start creating things that are just… Like, I worry sometimes that this 2Nite Show thing is too esoteric or too crazy, but it was an experiment and it was something I wanted to put out there and see what it would look like, and I’m proud of it.

But I think that there are benefits to both. There are benefits to tons of freedom to do whatever you want and there are benefits to having to work within the confines. With Late Night I have to play by the rules of the show, but I don’t find that bad – I love it. I love trying to figure out something that works that is both my voice and the voice of the show. It’s a really fun challenge.

By the way, I didn’t realize until recently that Chestnut Walnut Unlimited is a real production company. I thought it was just a gag at the end of your videos, but it’s got a website and everything!

I mean, it’s barely legit. [laughs] Like, it is and it isn’t. We have an office that’s the size of a handicapped bathroom in Bushwick.

Wow, it even has an office? That’s definitely legit.

Yeah, Joe did Talks You to Sleep out of there, and it is a new company, but we’re definitely trying.

So you guys plan to stay busy with that in the coming months?

Yeah! I mean, we do all the Trump things, 2Nite Show, Joe Pera Talks You to Sleep, How to Make It in USA, and they have a couple other projects they’re working on with people outside that group. We’re definitely trying to make it a real, tangible company.

Joe’s Late Night standup set from last month was fantastic.

It was so good. The amount of courage it took for him to do a two-minute a cappella joke is crazy. It was so good.

Check out O’Malley’s 2Nite Show Starring Johnny Carson below:

Conner O’Malley, the New King of Weird