a long talk

Conner O’Malley Opens His Digital Womb

The unhinged king of super-online comedy is giving fans a new way to mainline his weird, manic creations.

O’Malley on the USS Intrepid in New York. Photo: Adam Powell
O’Malley on the USS Intrepid in New York. Photo: Adam Powell

Since Conner O’Malley was hired to join the inaugural writing staff of Late Night With Seth Meyers in 2014 thanks to the strength of his viral Vines, the comedian has built a cult following through his vast array of videos featuring blustering, deranged American men teeming with misdirected fury — guys who think Benghazi would’ve never happened if the troops were sponsored by Under Armour, dudes who believe the NASDAQ’s rise and fall is directly tied to their child-visitation rights. Whether hosting a talk show in a polluted river, saving malls from both economic collapse and ISIS, or trying to reboot the Irish mob, O’Malley inhabits manic characters holding cum- and Monster Energy–stained blueprints for how to restore the United States to its postwar eminence. Throughout all his work, the comedian has remained faithful to his very distinct — and very loud — voice.

While writing on some of the most beloved niche comedy shows of this decade, such as How to With John Wilson and Joe Pera Talks With You, the latter of which he executive produced, O’Malley has also spent the last several years developing and shooting his own TV pilots. In the midst of these ideas not going to series, as well as major upheavals in the entertainment industry, O’Malley has decided to launch Endorphin Port, a site where he can directly sell videos to consumers while also showcasing new experimental projects. On September 7, O’Malley teased the site by announcing one of its free projects — the not-an-AI-bot named Jeremy — and today he premieres The Mask, a short film following one man’s journey from improv-comedy superfan to conspiracy vigilante in Los Angeles. Ahead of Endorphin Port’s launch, the typically media-shy comedian spoke about the site, the Chicago-suburbs mindset, Halo, his early internet use, Vanilla Sky, and the future of his career within the Hollywood system.

You’re launching a new site, Endorphin Port, to premiere and fund new videos and projects outside of the studio system. A Conner O’Malley ecosystem. But maybe you can, in your own words, explain it better than I just did.
I wanted to avoid subscriptions and have a pay-per-view platform that gives a cleaner exchange between me and the person who’s purchasing it, so for a pretty low amount of money, people would be getting back something. And I have a couple other projects that I’m working on where you don’t have to pay that are fun and kind of abstract, and I thought this would be a good place for them. I really like the idea of “Here’s the price, here’s what you get.” And then for people who are eager to support, giving them an opportunity to do that is very nice.

Okay, so it’s not a Patreon-model, $5-a-month sort of thing.
I think my output isn’t high enough for that. Patreon is great — I’ll easily subscribe to a podcast I like to get another episode a week — but these videos just take so much time and energy. It’s funny to me that the classic “buy a ticket, watch the movie” is now like a new model for Hollywood.

So stuff that is on a more regular weekly basis, like podcasts or talk shows or whatever, that’s not what you’re trying to do. It’s mainly a hub for new videos by you and maybe some of your frequent collaborators.
I really love putting out stuff for free. I’m not going to stop doing that. That’s something that I think is so fun. If you’re into my stuff, all of a sudden, one day, just no announcement, there’s a video and you get to enjoy it. It’s just kind of like, “Here it is.” I really love that.

But I’ve definitely hit a ceiling with what I can do with no-budget stuff. Not that I need $300 million or something like that, but one of the ideas behind this website is I’m not going to take this money and then spend it on a car or something like that; it’s going to be put into the next project. Hopefully it’d be a good subsistence-based model — like you’re paying to watch The Mask, but you’re also funding the next thing. I pay everybody that works on these videos out of my own pocket, so it would just be nice to have even a very small budget for the next thing.

What else can we expect to see on Endorphin Port?
Well, soon they’ll be meeting Jeremy, the world’s first fully synthesized human consciousness on the computer. It’s not AI, it’s a real person. You can speak to him at EndorphinPort.com. There’s a VR thing we’re working on that’s still in the early stages. There’s a lot of stupid shit I’d like to do with it. I’m not trying to be coy about it. But eventually, people can enter the Endorphin Port and experience what life would be like free of flesh and living fully inside of the computer.

Was creating Endorphin Port a recent idea, or has it slowly evolved over the last few years as the pandemic and strikes upended everything?
Definitely. The pandemic was something where I felt my output increased just because I had a lot more time. Then when we came back, it felt like the TV-and-film industry wasn’t quite what it was pre-pandemic. Then the strike shut everything down.

But I think the motivation behind it was just really to have a place where I could have a little bit of funding. Because, again, all the editors, everybody that acts in it, any crew that we have, I pay them. Not like friend rates, but their rate. And while they’re not giving me the rate they would give to Audi, I want to pay people. I’ve always hated this culture around internet comedy that’s like, You’ll do it for free because it’s fun, and you get the experience and you get to have Fruit Snacks.

The character you play in these Endorphin Port videos is lamenting about the current state of the internet. How old were you when your family first got the internet?
Oh man, I’m 19 years old, so … No, I feel like we got dial-up when I was 11.

What were you up to as an 11-year-old into your teen years on the internet?
Obviously, the first thing everybody does is pornography. But I remember pre-puberty, being online and not really knowing what to do with it, going to Yahoo.com and just typing in “G.I. Joe” and scrolling what came up. I remember looking at the CD-ROM Wikipedia, like pre-Wikipedia. I think it was called Encarta? I’m dyslexic, so I’ve always had a really hard time reading. So early internet wasn’t super-interesting to me. It wasn’t until YouTube and stuff like that came about. It’s funny to me that I wasn’t a super-online guy until video came out.

What about nowadays? What are you watching on YouTube?
I watch … I almost don’t want to say.

You don’t have to blow up any spots.
I’ll do this thing every once in a while in my live shows. I used to switch over to my laptop and I would start projecting it, and then I would go through my open tabs on my Chrome browser, and everyone thought it was a joke. But it was like, no, these are all the Wikipedia pages I have open. My one friend afterwards was like, “That’s maybe the most insanely personal thing I’ve seen somebody do — show that they have three different tabs open for Timothy McVeigh.”

I’ve been getting into watching YouTube Shorts. Something’s going on there that’s like the Wild Wild West. That algorithm is out of control.

What is it about YouTube Shorts? Because I watch a ton of YouTube, but I tend to skip those.
Every time I go on TikTok, I’m like, Oh yeah, they got me. They fucking got my ass. Yeah, totally. This is great. I love this. And then Reels is kind of the half-assed version of that. But Shorts is like going into a knockoff Spencer Gifts where they have knives and shit and posters, and they have all these $10 huge swords. With YouTube Shorts, I think they’re trying to grow it or they’re trying to build it, so they’re loose with the algorithm. It seems to be not super-populated, and instantly you get hit with the most hard-core Ukrainian war footage and stuff. It’s like, Oh, God. It’s less addictive in that sense.

Were you a Rotten.com guy when you were younger?
No, I feel like I would do eBaum’s and Newgrounds.com.

You have so many Halo references in your work. Are you a gamer?
Fortunately, no. I do not have gaming disease again. My hand-eye coordination is bad. It’s also why I’m not good at sports. Halo to me is … I remember being over at somebody’s house in a basement that’s half flooded and two people playing Halo and everybody’s smoking weed — like 15 guys in a room watching two guys play Halo. I think it speaks a little bit to attention span, where watching two people play Halo all night was like, Yeah, this is fine. It’s equal to watching a movie, just staring at the TV. I feel like that age of Halo for guys our age is very evocative. You look at boomer directors, and they’re obsessed with fucking in cars as teenagers. And our generation is obsessed with playing Halo with 15 men in a basement.

I didn’t watch the Halo TV show, but I did see that one episode was devoted to Master Chief losing his virginity, which sounds like a throwaway joke from one of your videos.
How did they not make that fucking movie, the Halo movie? I also heard — I don’t know if this is true — but I heard that in the pitch meeting for the Halo show, they had four tall guys in Master Chief outfits walk into the room that they were pitching and just stand there while they pitched. And recently, I was at La Guardia, and I saw a guy in a Master Chief outfit walking around the terminal. I was so pissed that I couldn’t pull out my phone in time. They were doing some kind of event with, like, Olympians, and they had a Master Chief guy there.

“I think the motivation behind it was just really to have a place where I could have a little bit of funding … I want to pay people. I’ve always hated this culture around internet comedy that’s like, You’ll do it for free because it’s fun, and you get the experience and you get to have Fruit Snacks.” Photo: Adam Powell

Going back to your longform videos: You’ve made these pilots and sizzle reels like TruthHunters.com, The Mask, and Content Guy. Could you tell me a little about them?
Content Guy was a pilot kind of similar to TruthHunters. We shot it in 2019. There’s a piece of it online — the “cuck a fan” video with Tony Camarabi is from it. It was another sketch pilot thing for a basic-cable network. It was super low budget, and I think it was thought of internally at the network as more of a pilot presentation as opposed to a full-blown pilot.

This really good producer I work with — Jon Benson is his name; he was this Daily Show guy — he took an incredibly small budget and stretched it really far and introduced me to a lot of great people on that project, like [field producer] Harris Mayersohn and [editor] Danny Scharar. But the network passed on it. I guess they were all going to watch it together as executives in the same room the week that the L.A. shutdown happened with COVID. Then the industry started to shut down and I was going to post it online, but my lawyer said not to because I would get sued. There was a former … there was a son of a sitting president, and they were like, “You can’t put it out. You’ll get sued.” So it’s just been, like, sitting.

Like, not as a character? He was literally in it?
Yeah, they were in it. I can’t say who.

Well, the last two presidents have had very prominent sons, so we can only guess who.
There’s great American princes roaming the streets on both sides.

So it sounds like it’s not going to be on Endorphin Port because of the potential legal issues, and the network probably still owns the rights.
Yeah, they own the rights. I mean, the thing is, if the network were to release it, they would be suing a huge media company; if I were to release it, they’d be suing an individual. And I think that’s how a lot of TV gets away with stuff like that. It’s a shame, because there’s an incredible crew of people that worked really hard and believed in it, but that’s just kind of how it goes. Development is pretty hard, and also, the pandemic didn’t really help it. It was just such a weird time where everything shut down.

But it was also kind of freeing, because after that, I felt like I had a pretty good burst of creative energy that I put into videos that felt better to do. It became less like, These have to amount to something in the television sphere, and more like, This is fun. What if I just buried myself in the woods? There’s a cave over here. Let’s go over there. Kind of more finding the joy in the doing of it as opposed to, like, This has to result in the outcome somewhere. 

And what about The Mask?
The Mask was a sizzle reel for a TV pitch. We got a very small amount of money from a production company, and then I put a lot of my own money into it. It’s where I met [producers] Reggie Henke and Katie Dolan, who worked on it. Danny edited it again. That happened during the pandemic, and it just kind of slowly started to turn into something else that wasn’t a sizzle reel, which are usually two to five minutes long, just to give you a little taste of what it’s going to be like.

We ended up having a 20-minute cut of this thing that’s more of a short film, but I didn’t know how to do a two-minute version of it that’s just me acting weird on the street. I don’t know if it would have conveyed an idea of a series. Then me and the production company parted ways, and I was like, I think this could be something else. It really occupies a zone that I think is interesting. It’s not a series; it’s not a movie. It’s kind of in the middle. It feels very much made to watch on a laptop in bed at three in the morning or for people to watch on Chromecast on a TV.

For a lot of writers and comedians, just pitching an idea or even yourself is a deeply uncomfortable experience. What’s it been like to pitch to execs over the years?
It’s generally been okay. I remember once a development person told me when you go into these meetings and you’re pitching, there’s a veneer of We’re just hanging out, we’re friends. Tell me about yourself. Oh, cool. That’s interesting. But you’re also being graded the whole time. People are evaluating you: What’s your vibe? What’s this idea? It’s very formal in that sense, but it’s also kind of loose and nerve-racking. It’s just another form of writing, and it’s a thing you have to get good at. But it’s really hard to convey an idea. It’s one of the most difficult things to do, but it’s not impossible. It just takes a lot of experience.

And pitching to Seth Meyers is definitely different than pitching to, for lack of a better term, suits.
I started on the initial staff, so they were really figuring out what the show was. And if you look at that staff, it’s a very weird mix of people in a good way. It was just stand-ups and sketch people and Onion people, Second City, and they found me on Vine. It was a good experience. They were like, “We want everything you have. We want to try everything.” There was a good spirit of that, so it felt easy to pitch a lot. That was my first ever professional gig. Seth and Shoe [Mike Shoemaker] and [Alex] Baze — they’re all incredible, very nurturing, and good with writers. They would give you feedback instead of stonewalling you and making you feel like you couldn’t get feedback or understand what they wanted. That was a great education. It felt like a good apprenticeship.

Besides Late Night, season two of How to With John Wilson is your most notable job as a hired hand. Based on your interests, I’m guessing the MRE episode was your idea.
I don’t know. I think that might have been there before. I’m very proud of working on that show and very honored to have been a part of it. Another great, weird staff. That was super-fun. I was just talking to somebody who worked on the show, Chris Maggio, the other day about it, and we both feel like our contribution to it is very limited. But I still have this deep pride, because just the nature of that show, it’s so autobiographical. There’s so much of John in it; it’s so based on his life. It was a really fun writing gig where he would just kind of be like, “I don’t know, maybe you should do that thing you just said. That sounds funny. That sounds good.” I’m pretty sure he had the MRE thing before I got there. It’s hard to tell.

So it was Susan Orlean’s idea.
Susan Orlean is a prepper. She lives in a missile silo in Kansas.

Could you talk about what some of your frequent collaborators — people like editor Danny Scharar, animator Cole Kush, musician Mikal Cronin — bring to your work?
If it can just feel like you’re hanging out and then you’re making something too? That’s the best. That’s the privilege of this job — feeling like, Oh man, I get to go in a room and just do bits with people from nine to five and laugh all day, and we write some of it down. 

Cole, specifically, he’s a great guy. I saw the Adult Swim pilot, Dayworld, he did with Jay Weingarten and was just blown away by it and thought it was so funny. And then Cole and I started talking more. He’s such a sweet guy, and there’s a sensitivity to his work. It reminds me of King of the Hill or a lot of Mike Judge stuff.

Mikal Cronin is somebody that I’ve been a fan of his music for so long. I heard he was a savant with a bunch of different instruments. Every once in a while, I’ll ask, “Could you do a saxophone solo?” He works really incredibly fast, and I get the stuff back and am like, Oh my God. This just elevates everything to a completely different level more than I could ever have imagined on my own. And another sweet, nice guy.

And Danny’s just incredibly talented. So much of The Mask he found through editing, and he really put a lot of himself in it. In collaborating, I always try to create an environment where I want people to creatively invest in the project and feel like they can have a little bit of ownership over it: I’d rather see an idea that you have than you pitch it to me, so if you have it in your head, go and try it. Maybe that’s more from my sketch and improv background, where there’s that invitation to the person you’re working with. Because I understand what it means to put your ideas into something and not be able to invest in it creatively.

One of my favorite videos of yours, one that I think connects together all the recent stuff you’re doing, is Leather Metropolis. How did that come together? How soon into lockdown did you decide to use this once-in-a-lifetime opportunity to shoot in an empty Times Square? Well, not once in a lifetime, because Vanilla Sky did it first.
If 9/11 didn’t happen, the trajectory of Vanilla Sky is what media was going to be. No shade to Vanilla Sky, but that’s what everything was. And then 9/11 happened. And they’re like, “We’re not doing that anymore.” Then everything shifted to Southland Tales. I remember watching Vanilla Sky as a kid and being like, I’ll never understand this art. I don’t know what this is.

500 Cigarettes was one I shot in the first week of lockdown. Even before the lockdown, I remember riding my bike down the middle of Fifth Avenue on a Saturday night, and there was no traffic. I have a video of that and just being like, Whoa, this is weird, and then utilizing that for the video. Leather Metropolis felt more experimental, where I’d go out, shoot stuff, and send it to Danny. He would edit it together, and I’d send him some voiceover. We had this process of writing and shooting simultaneously and editing until we had a thing.

I remember shooting in Times Square when some guy on a bike came by and tried to steal a tripod. I had to yell at him. He was like, “Sorry!” I don’t know if he had seen me. I also met this Irish guy in the middle of Times Square, and he contacted me afterwards. We met up in London recently. He was just this college kid who was trapped in America, and then he goes to Times Square to see it, and it’s completely empty except for me in a leather trench coat.

You grew up in Chicago proper, but a lot of your videos, whether it’s explicitly said or not, really tap into this specific mindset of living and growing up in the Chicago suburbs. Where does that come from?
They’re just funny to me, the names of them. They all have their own identity. The south suburbs are different than the North Shore suburbs. But for the most part, you can’t tell the difference between Des Plaines and … I can’t even think of another. They’re all just like this weird …

Evanston. Prospect Heights.
Evanston has a vibe. Maywood has a vibe. Berwyn and Cicero obviously have a mob history. I worked for 1-800-GOT-JUNK in Chicago, and we did a lot of jobs in the northwestern suburbs. So it kind of comes from that a little bit. But I don’t know, the Chicagoland area sometimes can feel like just this blob of hegemonic … it all feels the same.

Arlington Heights is getting the Chicago Bears.
I had a distant cousin who was mayor of Arlington Heights. I remember meeting him once, and he had a cop car for a regular car.

A lot of the dudes you portray are sad guys just kind of drowning in despair, like the Wisconsin Dells vlogger or the dad from Joe Pera Talks With You. But what I really like about them is that there’s always a layer of sympathy. There’s not a lot of meanness toward them. Even when you’re making fun of Trump voters, it’s never like, These guys are dumb for voting for Trump. It’s more like you’re making fun of the environment they grew up in that’s led them to this stage in their life. Could you talk about how you try to make sure that your character work doesn’t go over the line into being unkind?
I always think about how American Movie has such a good balance of that. It so easily could have been like, “He looks horrible,” but you’re rooting for him so hard, and there’s an in on that.

It just might be the way my mom raised me to be polite. It might just be a midwestern Irish Catholic thing. But I think it’s also approaching the writing of it from character work, as opposed to an intellectual space — where it feels more intuitive, as opposed to intellectual. I’m a fucking dumbass. I’m stupid as shit. If you talk to my brothers, they’d be like, “In high school, we were like, ‘What are we going to do with him?’” I wasn’t good at school. I’m not good with my hands. I would have been living in the basement of my dad’s house: “I don’t know. He said he put in an application at Target. We’ll see.” I feel very lucky and privileged to be where I’m at now. But I think there’s not a lot of dumb-guy representation in the media.

In one of my intro guides to your stuff, I compared you to Chris Elliott in that you guys both started on Late Night then built this cult following. Were there any career roadmaps that you admired?
That’s very flattering to be compared to Chris Elliott. He’s obviously the king. So funny.

I think coming up in the Chicago comedy scene, there was a little bit of a path — obviously the SNL connection. But growing up, I remember WTTW Channel 11 did a documentary on Second City called Second to None. Tina Fey was in that, and Scott Adsit. Kevin Dorff was one of the cast members. I remember watching that as an 11-year-old, and then seeing Dorff pop up in Conan sketches and being like, Oh, fuck, and then going, Oh he’s a writer, and then seeing [Jon] Glaser and all these other people that had Chicago connections who would then go on to write at Late Night — it was something that was like, Oh, that’s possible. Like, if you were to do sketch and improv in Chicago, that was a path.

But in terms of emulating career paths, that’s something you can’t be too married to, you know? I feel it’s better to be adaptable. It feels a little bit like trying to study the right place to put your fish hook in the water, where it’s more important to always be casting and trying stuff. With Late Night, it was a weird series of events, and I got very lucky. But The Unabomber is someone I really admired and whose career I studied. MKUltra, Harvard, Montana, Supermax.

“I just truly feel like kind of a dumbass who’s lucky to be here.” Photo: Adam Powell

Going back to Endorphin Port, you’ve built this legion of devoted fans — hopefully paying fans — while spending years trying to get stuff made by Hollywood. If Endorphin Port takes off, is there ever going back to the old model for you?
Doing Endorphin Port isn’t necessarily like “I’m never going to pitch anything ever again” or “I’m never going to work in Hollywood ever again.” It’s more like I had this idea, and I had this project, and they all kind of fit together nicely in a way. Sometimes a lot of my videos might start out as It’d be funny to tweet this or post a picture of that, and then I sit on it and go, Well, what if I added this to it and that? and then it builds out into, Oh, this feels like a video. You’re listening to the idea and what it needs to be, as opposed to trying to push it to something.

There are ideas I have where I’m like, That’s a series, and I could totally see an episode like this or an arc for this character. I feel very lucky to be alive in a time where you can do that and there’s access to the technology, because when we were growing up, I knew one kid that had a camcorder and even then, how do you edit it? It was all about access to film. Now children are born editing things on phones and iPads and shit, and nobody does cursive anymore. They don’t know how to do long division.

Also, I don’t want to create an echo chamber for people. When I’m working on this stuff, I do make it hoping most people can watch it and enjoy it. I understand that it’s an acquired taste and a lot of people don’t like seeing me eat human shit or getting sprayed with shit or pissing myself. Getting at the Hollywood of it … Yeah, I don’t know. Again, I just truly feel like kind of a dumbass who’s lucky to be here.

Conner O’Malley Opens His Digital Womb