People think this is the American Dream
The young laughter king Conner O'Malley on making the best comedy special of the year so far, RAV4 excellence, when clothes that look funny become cool & more
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— Jonah & Erin
If we put together a Spyplane Pantheon of Laughter Kings (in the blessed gender-agnostic sense of “king”), several certified-comedy-genius Spyfriends would be in its uppermost ranks, including Nathan Fielder, Kate Berlant, Eric Wareheim, The Kid Mero — and today’s guest, the brilliant Conner O’Malley.
You may know Conner from I Think You Should Leave with Tim Robinson and Joe Pera Talks With You, from his stretch writing and performing on Late Night with Seth Meyers, or from the videos he’s been posting online for years. He moved to NYC from his native Chicago with his wife Aidy Bryant when she got cast on SNL, at which point he worked as a dog walker and started shooting clips on his phone in between walking dogs. Some are 6-second Vines, some are relatively straightforward sketches, others start unhinged and sprout disconcerting subplots as they go, and sometimes it’s thrillingly impossible to find the line in his videos between “comedy” & “avant-garde video performance art.” (We link to a bunch of our favorites down below.)
If there’s one major theme running through Conner’s comedy, it’s a deranging, internet-age loneliness and the way that loneliness can beget paranoia, rage, profound depression…. and hilarity, baby.
It’s all there in Conner’s first-ever hourlong special, Stand Up Solutions, which he debuted on YouTube last month, and which is the funniest & most unpredictable special we’ve seen in years. He plays an entrepreneur trying to pitch investors on “the world’s first A.I. stand-up comedian,” trained on surveillance-capitalism data harvesting, plus “one-third of everything on Funny or Die Dot Com and every episode of Real Time With Bill Maher” except “the episodes where Bill says the N-word.”
It is packed with jokes, satire and pathos, and it made me feel bad about being alive now, in a good way.
So the other day I (Jonah) was stoked to hop on a Big SpyLink Transmission with Conner to talk about Stand Up Solutions, loving the Toyota RAV4, unmakeable dream movies, how trying to dress like a poor person from the midwest got cool, and more “unbeatable topics.”
Blackbird Spyplane: Stand Up Solutions is so good. I’ve watched it twice through and there’s all this stuff I missed the first time. A lot of people I know who are longtime fans of yours have been telling me how much they love it, and it’s come up with people where this is the first thing you’ve done that they’ve seen, and they’re blown away, too.
Conner O’Malley: “People are liking it, it’s nice — I took it on the road for a long time, so it’s cool to finally have it out there.”
Blackbird Spyplane: A lot of your comedy is about exploring different parts of a very contemporary kind of loneliness. We were told the internet was going to be this liberatory, communal technology, but instead the companies that got their hooks into it want to turn us into consumers, brands and salespeople, all at the same time. And that feels s**tty. In this show you’re looking at that loneliness through the lens of a traveling A.I. salesman. How did the idea come about?
Conner O’Malley: “A few years ago I was writing at my computer, and the idea just hit me of being onstage with a company called Stand Up Solutions — this image of me pitching a tech company, but related to stand-up, which is so unimportant in the scheme of things. Also I was binge-watching every episode of Shark Tank, and seeing that kind of desperate yet weirdly confident energy a lot of the people on that show have, pushing themselves into this situation where you’re like, ‘You don’t need to do this.’ But I think a lot of people are like, ‘This is the American dream.’
“Initially I was envisioning it as a road-trip movie, but then I was like, I’ll just work it out on the road, then write a script and shoot that — then we taped it and tried to sell it, and nobody was interested, so we put it out on our own.”
Blackbird Spyplane: That’s a route more and more comedians seem to be taking these days, especially with the big streamers buying much less cool s**t. It might be for the best.
Conner O’Malley: “Yeah I enjoy the freedom the internet gives you of, like, not having a strict form. But I don’t like stuff that wastes people’s time, either.”
Blackbird Spyplane: There’s an extended bit about how much your character loves the Toyota RAV4. We love the RAV4 at Blackbird Spyplane, too, but only the early ones (above top row), which were so strange and cool-looking. Almost like an anime vehicle in real life. The OG two-door RAV4 feels emblematic of this moment when the American automotive market could still accommodate cars that tight. Whereas the newer RAV4s are not swag. They could be any SUV.
Conner O’Malley: “Midsize crossover SUV.”
Blackbird Spyplane: That’s so funny. Why’d you choose that as the car he loves?
Conner O’Malley: “That part’s actually very genuine: I have a RAV4 and I love it. This was my first imported car, and the quality is incredible. But yeah I also think it’s really sad that every car looks the same now — there’s no difference betwen the CRV and the RAV4 and any of these cars. And it’s what everybody wants. I think it is emblematic of this transitional bastard period we’re in, especially in terms of design. It’s kind of a shapeless time.”
Blackbird Spyplane: I was just listening to the director Jane Schoenbrun talk about I Saw The TV Glow on the A24 podcast, and they mentioned this unmakeable dream pitch they have for an “Apatow-style school shooter comedy” starring you as the cop tasked with designing the active-shooter drill for the local school system. Do you have any unmakeable dream pitches you want to share?
Conner O’Malley: “Pretty much every idea I have is like that. There’s so much stuff I’ve pitched where I think it’s good, then I hear it out loud in the room and go, This is horrible, why did I think this would work? It’s hard to choose one to talk about, though, because in my mind I’m like, ‘…. they could still happen.’
“One thing I wanted to do with the road-trip version of Stand Up Solutions was build a real version of KENN, the AI comedian, with this really complicated powertrain that, instead of producing exhaust, has a tank that fills up with an explosive, toxic liquid that comes out of a little spout where his crotch is. I wanted to shoot a real-world thing of me on the bed of a pickup truck, essentially jerking off KENN trying to get this disgusting, foul-smelling toxic liquid out of him, and also this loud beeping is coming from him when he needs to be emptied, and people are like, What is this? and I have to shout at them to get away.
“That was gonna be a big part of the movie: It’s the middle of the night and KENN starts beeping, and I have to drive him out to the middle of a field.”
Blackbird Spyplane: One thing that struck me watching through your old videos is that the costumes you choose for your characters are often inadvertently pretty sick — like the camo-print Underarmour hoodie and frameless sunglasses on the guy defending the outlet mall from ISIS, or the Asics, jorts, airbrushed Jay Leno tee, cycling blades and Raytheon cap you wear in your Jay Walking video. These are outfits you could see in Bushwick circa 2024 with very little modification.
Conner O’Malley: “It’s funny, now it’s just about trying to dress like a poor person from the midwest, huh? The sunglasses are cool, though, I’m glad they’re having a moment.
“But yeah, wardrobe in comedy is super important. I remember watching this video about the making of There Will Be Blood and how much time they spent just trying to figure out Daniel Plainview’s hat. There’s this thing where the right piece unlocks something — it does so much work, writingwise.”
Blackbird Spyplane: It’s always fascinating to me how the right look can swing from laughable to cool. In Leather Metropolis, from 2020, you wear an outfit that’s basically what a Blade extra would wear, which at the time was a clearly comical choice on its face, but for the past few years that exact style has been popping up on style moodboards.
Conner O’Malley: “I remember leaving my apartment dressed in that outfit at 3 in the morning, people seeing me on a leather duster on my bike, riding to Times Square, feeling really stupid. It reminds me of hearing Tim and Eric talk about seeing hipsters basically start wearing their wardrobe from Awesome Show, and they were, like, ‘OK, we have to find a new move.’ But it’s shocking to me that the 2000s are back, fashionwise, because that’s such a repulsive time in my mind. I’m curious what you think.”
Blackbird Spyplane: It felt pretty grody while it was happening, but I try and leave the door open to the possibility of discovering something I might have been too quick to dismiss the first time around.
Conner O’Malley: “It’s funny to see jorts become popular now, too, because when I shot that video I felt incredibly self-conscious in between takes. In my personal life my thing is, I want to look at a picture of myself in 20 years and not go, What was I doing? I tend to keep it pretty conservative and basic. So it was actually kind of freeing to go out in public dressed like that.”
Blackbird Spyplane: All right, finally, I asked you to share a cherished possession with us, and you chose a little hockey trophy. What’s the story?
Conner O’Malley: “This is a 1995 Boys and Girls Club Floor Hockey championship trophy, from the Chicago Park District. Basically there’s a Boys and Girls Club in this park called Paul Revere Park, and growing up my parents always signed me up to baseball, football, basketball, and I hated it, but for whatever reason I was really good at floor hockey. There was a very small tournament, and I won this. I must have been like 9.
“But that club is a really important place in my mind — just the idea that there’s a space that’s just for kids, and it’s not a mall or a school or a church.”
Blackbird Spyplane: There was that classic ‘80s-era movie premise of, ‘We have to raise money to save the rec center, because greedy developers wanna bulldoze it and put up a condo.’ And the condos basically won that war.
Conner O’Malley: “Yeah, they did. But this club is still around, thanks to the Chicago Park District’s incredibly corrupt system of patronage jobs. The guy who ran the park, my dad was friends with him, he’d just sit in an office reading the Sun-Times and the Tribune all day. I remember one time, he said, How old are you? and I said, 5, and he said, Man, I wish I was your age. I was, like, Why?? It always stuck with me. The parks district is filled with people with high-paying jobs and benefits who don’t have to do anything but get the vote out for whoever’s in office.”
Blackbird Spyplane: And in this case that protects a “market inefficiency” like a rec center, which is cool.
Conner O’Malley: “Oh yeah, patronage is fine to me. Obviously I don’t like corruption if people are getting murdered or something. But if you can get a fake job from the park district? Sure, why not? Do it.
“I’m not talking s**t on the parks, though. I spent so much time there as a kid, I feel like it’s a way you can make kids’ lives better, and make communities better — putting money into the parks system, having a pool and a playground and trees to climb. It was so fun. And it was all a direct result of these patronage jobs, because they needed a system to dump these people where they couldn’t f**k anything up too bad.”
Conner O’Malley’s site is here and his YouTube channel is here. He’s on IG here.
After you watch Stand Up Solutions, check out his shorts, including Irish Mob, Leather Metropolis dir Michael Bay (2003), Hudson Yards Video Game, Jay Walking 2K19, and Howard Schultz tapes (4K FULL MOVIE 2019 FREE).
Thank you, BBSP, for producing this incomparable sletter on a weekly basis. This was a real treat. A rare glimpse of just how intelligent and humane the man behind the "character" is. Big love and praise to all the great alt-comics working today, but O'Malley might be in a class all his own. He has a clairvoyance about American culture like I've never seen. The art is bewitching, depraved, hilarious, and completely singular.
We NEED to bring back the Irish Mob...