Richard Eagleton is ecstatic. The aspiring tech entrepreneur from Des Plaines, Illinois, has just shown off his great invention, KENN, the world’s first AI stand-up comedian, “powered by 5G for 100 percent accurate comedy.” After KENN delivers a couple glitchy, half-baked jokes about self-checkout machines, bad dates, and being a “fucking garbage person for real,” Eagleton bounds on stage and says with frenzied glee, “That was incredible! Oh my God, everyone was laughing, everyone was experiencing social cohesion! There were no stabbings, there were no shootings, no robbery!”
Over the next hour, Eagleton will feverishly pitch himself and KENN with a delusional determination that slowly crumbles under the weight of his own shortcomings and the reality that nobody asked for his dumb joke-telling robot. It’s a descent into madness that could only take place in 21st-century America, and could only come from the mind of Conner O’Malley, the comedian who created and plays Eagleton in his new hour-long special Stand Up Solutions (available on YouTube).
O’Malley has collected writing and acting credits on shows like Late Night With Seth Meyers, I Think You Should Leave, and Joe Pera Talks With You; and he’s appeared in movies like Palm Springs and Jane Schoenbrun’s latest, I Saw the TV Glow. But he’s probably best known for the videos he’s been posting online since Vine. He primarily uploads to YouTube (with other clips scattered on Instagram), where his channel has garnered over 16 million views and 217,000 subscribers since it launched in 2006.
Richard, like many of O’Malley’s characters, is a frothing, frenetic striver, whose internet-addled obsessiveness teeters on the edge of full-blown derangement (and sometimes goes fully overboard). O’Malley has played guys who protect Wisconsin outlet malls from ISIS, compensate for failed improv careers by becoming manic conspiracy theorists, pursue dark rebrands of Mickey Mouse, smoke 500 cigarettes for 5G, destroy their bodies for the presidential campaign of a Starbucks CEO, or blame Drake for their 103- degree fever while DMing him weird Family Guy porn.
O’Malley’s comedy operates at high-decibel, high-concept extremes, but his great talent is uncovering that nugget of humanity that makes you actually want to spend time with these characters. In Stand Up Solutions, O’Malley grounds Richard’s wannabe Silicon Valley posturing with relatively humble aspirations: a happy family, a garage full of Toyota RAV4s, and, in one of the show’s best punchlines, delivered after KENN asks a flustered, distraught, humiliated Richard what he really wants — “an all-brown house.”
“I think that’s honestly probably closer to my desires,” O’Malley says. “Eating McDonald’s in a brown house is nice… If you’re gonna spend a full hour with a character, you want it to be somebody that you kind of like. You have to do it with love. You can’t shit on them.” (This maxim even holds for the #VanLife vlogger O’Malley plays in “PVC Feces Rig Tour,” who literally winds up covered in his own shit.)
O’Malley, who grew up in Chicago and came out of the city’s comedy and improv scene, has been performing live since he was 18; but Stand Up Solutions was his first time doing a full hour in character and taking a show on the road. He toured and tinkered with it throughout 2022 and 2023, fine-tuning Richard’s PowerPoint presentation with the Berlin-based comedian-artist Jason Harvey, and KENN with Canadian animator (and frequent collaborator) Kole Cush. Stand Up Solutions was filmed live last October in Brooklyn, directed by Harris Mayersohn (another frequent collaborator), on a modest budget. The goal was to capture a “snapshot” of the show in that moment, O’Malley says, and hopefully attract a buyer who might put up the money for a “bigger version.” There was some interest, but nothing materialized. So, O’Malley did what he’s always done: Put it online.
“Ultimately it made more sense because I had a subscriber base and people who would want to watch it,” O’Malley says. “I’m just starting to post about new dates, so I’m curious to see how the special feeds into that. But that’s kind of the model now: You do the special, then you can hopefully size up.”
Since its release in May, Stand Up Solutions has garnered over 400,000 views on YouTube and inspired some astute criticism about American desperation in the 21st century, Silicon Valley’s relentless and unnerving techno-optimism, and our uncertain, AI-driven future. O’Malley, for his part, prefers not to think too much about any of it. He doesn’t do many interviews, and he’s clear about why: “I hesitate to intellectualize a lot of stuff. It feels better to keep it intuitive.”
That reservation is understandable enough, especially since everybody knows there’s no better way to ruin a joke than by explaining it. But O’Malley’s work frequently encourages such contemplation. He gets at the stark-raving-mad essence of our contemporary collective psychosis — terminally online as the real world burns, rabid with desire for unimportant things, unable to attain or maintain the human connections we need. Richard Eagleton embodies all of this, but O’Malley states plainly: “I think I was more interested in doing jokes about Des Plaines, Illinois, than I was about making big points. It just felt more natural.”
O’Malley, who’s married to the actor and former SNL star Aidy Bryant, is currently in Los Angeles writing and preparing to hit the road again with a new show; he’s also starting to screen a new short film he directed and wrote with Danny Scharar, Rap World. The two times we speak by phone, he takes the calls outside, walking around as we chat about everything from AI and crowd work to David Lynch, The Simpsons, and “Midwest King” Bob Seger. Despite his wariness about overthinking his work, O’Malley is thoughtful and considerate with his answers — but always true to himself.
“It’s incredibly nice that somebody would devote that much thought to [my work]. It’s flattering,” he says when I ask him about the kind of deep thinking and criticism his comedy often inspires. “[But] I’m just trying to be stupid on the computer, you know? I’m trying to entertain. Sometimes people want to know, ‘What’s the idea behind this?’ And often it’s like, ‘I don’t know. It’s funny if I wore that hat and said that, right?’”
The following Q&A combines portions from two phone calls. It has been edited for length and clarity.
What was it like touring for the first time?
It was very fun. I mostly did the Midwest, which felt like a safe and comfortable ground for, “Is this viable?” This is the first time I went out and tried to sell tickets. It feels like an honest exchange of, like, showing up and trying to give people more than what they paid for.
It’s close to vaudeville, where you’re just this idiot going from town to town. But on the other hand, I’ve done manual labor jobs. So there is a feeling of, “I can’t believe I’m getting a check for this. This is insane. This is something I did for free for 10 years.” I’m trying to hold onto that.
You also went to the UK and Ireland. Stand Up Solutions is a very American show in a lot of ways. Did it translate well?
I did a week at the Soho [in London] that was sold out, and the audiences really got it. Then they were like, “Can you do another week?” That run was a little bit more rough. It felt like I ran through all the comedy fans that are into more American stuff. Then, on top of that, I ate something bad and had basically a month-and-a-half-long, 1800s-level [bout of] dysentery. I was onstage trying not to shit my pants. I lost like 15 pounds. Scotland, Belfast, and Dublin — those were all great. But I was just ill all the time, sweating. I remember one night at the Soho, I had taken a piss before getting on stage and dribbled some piss down the front of my pants and somebody tweeted at me afterwards, “You pissed your pants during the show.” And I was like, “I don’t care.”
You’re Irish-American — what was it like performing in Dublin and Belfast?
That was the best. I think Dublin is my favorite city to do comedy. They were so warm. Dublin has a similar vibe to Chicago, where it’s not London, like Chicago’s not New York. I guess it’s a little bit more humble, for lack of a better word. I’ve gotten close with some comedians over there.
Do you see any similarities between their sense of humor and what you grew up with in your family?
I have Irish grandparents, like straight off the boat. I feel like it’s very similar to Norm Macdonald-style jokes, where it’s kind of anti-comedy. It’s not about being clever, it’s embracing being stupid.
How did this show begin? Was there a specific idea, bit, or character trait that really launched it?
It was a polo shirt. I went on CustomInk with an idea for a tech company for stand-up, and just designed the shirt. And I was watching a lot of Shark Tank.
With Richard, it feels like the obvious choice would’ve been to make him a kind of Elon Musk-worshiping entrepreneur. But his desires are very grounded. Tell me about that choice.
I thought less about this character in terms of a tech CEO and more like a guy that sells above-ground pools. A much more Midwest thing.
I remember one time, I was in Vegas shooting something with Joe [Pera], and we got a Lyft driver who was from Syria. He had a family and was obviously not happy to have his whole life uprooted and to be living in Henderson, Nevada. But he said, “In Syria, I was scared all the time. And I’m not scared all the time here.” And that’s a thing you kind of forget. Like, McDonald’s is kind of nice. You can get a fucking three-bedroom house in Nevada for what, $400,000? I feel like going after the tech people and the Elon Musk stuff has been done a bit too much.
Early on, Richard tries to show his commitment to fatherhood by saying he does a daily guided meditation where he imagines his family is murdered and he has to seek revenge like the Marvel vigilante the Punisher. That feels like a distinctly American fear.
I think everybody’s afraid all the time, and if you had a family, you’d be scared that they’re gone. But also, if you buy a gun, you kind of want to kill somebody, right? It’s kind of a waste of money if you don’t get to kill someone [laughs]. I’m kind of agnostic on guns, but that’s what keeps me from getting one — I don’t want to shoot anyone in the head.
You said that when developing Richard, you just wanted to make jokes about Des Plaines. So, what is it about Des Plaines?
Me, my mom, and my brothers got lost going there once, and that’s just been in my head. It’s funny to have pride for a suburb. Also, the McDonald’s culture is huge in the Chicagoland area because of [founder and native son] Ray Kroc and Des Plaines. [The first McDonald’s franchise in Des Plaines] is set up like a museum. I remember that being impactful as a kid — that they had a fake McDonald’s that doesn’t work, with 1950s mannequins inside of it, across the street from a brand new McDonald’s.
Tell me about bringing artificial intelligence into this show.
I had a couple of friends who got early access to [the AI text-to-image generator] DALL-E, Alan Resnick and Cole Kush. One night, we were hanging out and Cole typed in “infants working in an oil field,” and it was just hyper-realistic. I think about the plot of the Transformers movie, where the Transformers land on Earth and they can use the internet for data sets to learn English and all of our culture. These ideas of artificial intelligence have been in the media for like 20, 30 years, and it’s interesting to see it get closer.
The joke about Richard’s comedy bot KENN is that it’s trained on one-third of Funny or Die and all the episodes of Real Time where Bill Maher doesn’t say the N-word. Tell me about making this AI stand-up set. Were you tempted to use something like Chat-GPT to write KENN’s material?
No. I didn’t want to make fun of AI. I didn’t want it to be like, 30 years from now, like how Steve Allen would make fun of the Beatles. I was more interested in going after hack stand-up. I’m not an elitist and I like broad comedy; but when it’s lazy, I get upset by it. That was more what I was going after, as opposed to any sort of critique of AI, because it’s just gonna be a part of life.
How’d you make that connection between AI and hack stand-up?
This iteration of AI that we’re allowed to have access to, it’s kind of first-thought stuff. I feel like a lot of stand-up comedy that I don’t like is somebody who could go deeper but is not. It felt funny to build up this technology and then have it doing jokes that are so boomer Facebook.
The jokes feel more about everything around AI, and the people pushing it, rather than the tech itself. Like, eventually KENN tells Richard that AI stand-up is a bad idea, but he could be put to great use by a prison food services company.
That reflects back to an experience of Hollywood, where it’s like, “Charlie Kaufman is so funny, he’s so good, this script is so good — would you want to adapt the Care Bears Movie?” Or entrepreneurs on Shark Tank, who have a vision that doesn’t work, and there are five people saying, “Actually, it’d be better if you did this.” But they’ve taken so long they’re like, “I can’t give that up.” It’s very understandable.
You were already touring this show before the WGA and SAG strikes last year. Did the conversations around AI during that time have any influence on you?
A little bit. I‘m in the WGA and SAG, I’m pro-union, but I do think there’s a shift coming. Throughout the history of media, they’ve tried to stop [things]. “VHS is gonna ruin the industry, people taping songs off the radio is gonna ruin the industry.” Napster kind of did [ruin the industry]. You can go all the way back to sheet music. Every 10 years there’s been a disruptive technology that completely changes how people make money off music. Sometimes mainstream television and movies are a little insulated from it, but look at the impact VHS had on the porn industry, and then see what happened to movies. It reminds me of when paint rollers first came out — the painters union made them illegal. But then you look at something like parmesan manufacturing, and they’re able to hold onto what makes it special through being restrictive. It’s a delicate dance.
When you think about what’s coming with AI, are you hopeful that it might be put to good use, or do you have any big fears or concerns?
I’m hesitant to be proscriptive about it. I just keep thinking about, like, Pets.com. I think that the tech world… I mean, every business is this, where there’s an element of marketing and trying to sell stuff, and it’s undetermined by what this technology is actually going to do. Think about dynamite, where they were like, “Oh, this is gonna save lives.” Like any technology, it holds a lot of potential on the good and bad side. From my own personal experience, I use it a lot — videos, audio-visual effects — and it’s really helped me and a lot of my friends make things that, 10 years ago, we wouldn’t even have had the idea because it would’ve cost too much money. On the labor side, it’s scary. And it seems like nobody gives a shit about that.
There’s the copyright issue too, when it comes to how these large language models are being trained.
I don’t know what they’re gonna do about that. It seems like it’s already being trained on everything. You can’t put that back in the bottle. [The tech industry is] begging for forgiveness on that one and it seems like they’re going to get it.
KENN works by harvesting the data of everyone in an audience through 5G and crafting a set specifically for that crowd. That had me thinking about the way crowd work has really taken off in stand-up again. Is that something that was on your mind?
That’s a skill you have to develop as a comedian and the truly great ones are able to do it. It’s a very working-class thing to be able to read the room. And in my experience, it’s very Irish-American to understand, like, what’s the vibe here? And then adjust yourself to better fit in. I do love crowd work, I think audiences love it. People love knowing, “Oh, you just thought of that. You just responded.” I think a lot of stand-up purists are maybe not into it as much, and maybe there’s a level of jealousy that somebody’s able to break through with that. But I love it. I love seeing it. It’s that skill of, “I’m in front of this room, what are the boundaries? I’m going to push you just a little bit to that edge. How far can I get you? Oh, you’ve gone too far? I’m gonna pull you back.” Again, that’s another intuition thing.
The special ends with this “Classic Rock Guided Meditation” — where did that idea come from?
I have a video I’m working on called that. I’m still shooting it. But in Chicago growing up, there were like three or four classic rock radio stations. It’s such a huge genre that people love. It’s white culture — it’s the best we have [laughs]. I think I was talking to Cole about it, and I said something like that, and he was laughing, imagining trying to do meditation to “Sweet Home Alabama.”
The meditation ends on Bob Seger’s “Like a Rock,” which is a perfect song for that moment. Like, in the cultural lexicon it’s effectively a Chevy truck jingle, but really it’s a very moving song about a lot of themes your work deals with, like male vulnerability and dashed dreams.
I love Bob Seger, he’s a Midwest King. There’s a lot of songs that are like that, like “Glory Days.” Maybe I relate to it because I’m at that age, where you’re kind of looking back, but you’re not over the hill yet. But that song is really good. Also, a lot of people don’t like him, which is interesting.
I came to him very late. It might’ve been that Midwest sincerity put me off, or I just found corny, especially when I was younger.
Yeah, it’s like you want to be more Rage Against the Machine or System of a Down — “Fuck that shit, I want hardcore stuff.” I feel like this is the key to The Simpsons — they care about the emotional arc of the story, but the jokes are just as good. [David] Lynch is like this. I think a lot of people read in Blue Velvet him talking about the “bluebirds of happiness” as a campy joke, but I do believe he believes in that. I think he also believes there are [sociopathic criminal] Frank Booths in the world and is fascinated by it. Maybe there’s something about the Midwest where you’re able to hold both of those things at the same time.
A lot of your characters have similar qualities. What draws you to these guys with this kind of manic obsessiveness and rage?
Again, there’s not really a deep intellectual process. I’m a big believer in working from a place of intuition and starting there, as opposed to sitting down and writing on a piece of paper, “toxic masculinity ideas.” I often bristle at people writing about it. I think that’s what keeps me from doing interviews. It’s really just from a place of: Wouldn’t it be funny if I did this, or if that happened? It goes back to the Midwest and Irish-American stuff where it’s really bad if you’re trying to look smart.
I always think about Conan O’Brien for that balance of smart and stupid. Here’s a Harvard-educated guy who’s really sharp, but also just committed to the dumbest, goofiest things you can imagine.
The Simpsons and Conan were the two things that did that best. I remember hearing Jon Glaser once — and this is a very Chicago thing — say that people think that when he says something is so dumb, he’s saying that’s bad. But it’s actually the highest compliment you can give something. I definitely feel that way. I say that when I love something and it’s funny — “that’s really dumb.” But I’ve definitely been in writers rooms where I’ve said that and then had to explain, “No, that means good.”
From Rolling Stone US
