Late at night, when he should be asleep, Kyle Mooney searches YouTube for videos that nearly everyone else has forgotten. He recently sought out a candy commercial that he’d loved as a kid in the ’90s: a long-running television ad featuring real animals trying out to replace the Cadbury bunny. There’s a pig, a cat, a lion, a llama, and a tortoise. (They all fail to win the job.) Diving down these rabbit holes gives Mooney the same sugar rush he gets from eating a handful of Creme Eggs. “It’s incredibly comforting to me, almost to a place that I think is unnerving,” he says. “That’s not something I’m necessarily proud of. You know what I mean?”
I do. Like the comedian, actor, and filmmaker, I’m pretty obsessed with looking back into the past, at the kind of ephemera that will never be the subject of a Ken Burns documentary. As two guys in our early 40s, Mooney and I share a set of pop culture references: AND1 T-shirts, devil sticks, and the Talkboy, a toy voice recorder that was a hell of a lot more fun in Home Alone 2 than it was in real life.
Mooney, I realized fast, doesn’t believe in Tony Soprano’s philosophy that “remember when …” is the lowest form of conversation. “If there’s no harm being done, and if you’re still actively contributing to culture and society and not fully imprisoning yourself in a way that you’re putting blinders on,” he tells me, “I think whatever you’re into, it’s cool.”
The thing about nostalgia, though, is that it’s not art. “It’s not challenging to consume stuff that you know and love,” Mooney acknowledges. What’s hard is turning stuff you know and love into something new. But that’s what he’s good at. For a decade and a half, he’s been breaking down the TV, music, movies, fashion, and internet culture of his youth into spare parts and using them to build truly original material. “It’s the child in him that is connected to these things,” says Beck Bennett, Mooney’s college friend and former Saturday Night Live castmate. “It’s his culture.”
During his nine seasons on SNL, Mooney played characters like the terrible Clinton-era stand-up comic Bruce Chandling and the fake-tough, JNCOs-rocking teenager Chris Fitzpatrick. He cowrote and starred in 2017’s Brigsby Bear, a dramatic comedy about a boy raised in a bunker whose only entertainment was a homemade ’80s children’s show. And in 2021, he released Saturday Morning All Star Hits!, an R-rated parody of ’90s cartoons, on Netflix.
All of this memory mining has led to the Mooniest project yet: Y2K. His directorial debut, out on Friday, is an apocalyptic version of Superbad. Two high school besties go to a party on December 31, 1999, and when midnight strikes, what we were warned might happen actually does: The machines take over. The buddy horror-comedy, which he cowrote with his college friend Evan Winter, teleports the audience back to a time when teens communicated exclusively via AOL Instant Messenger, mom-and-pop video stores still existed, and nü-metal ruled the airwaves. In other words, welcome to the Kyllennium.
“Evan and Kyle lived and breathed this,” says actor Julian Dennison, who plays Danny, the Billy Blanks–trained half of the duo trying to save the world in Y2K. “It was like they just pulled these two guys out of high school from the ’90s, and they’re making this movie now.”
Mooney’s goal was to recapture what life looked and felt like when he was coming of age—basically a millennium-set Dazed and Confused (where modern technology tries to kill everyone). “Maybe this gives a glimpse into the late ’90s,” he says, “to a generation that didn’t experience it.”
The A24 film is, in reality, a do-over. On New Year’s Eve 25 years ago, when he was 15, Mooney didn’t go out. He stayed home and watched Carson Daly, Christina Aguilera, and Blink-182 on the MTV 2 Large Millennium Countdown.
A party that Mooney did attend is what inspired Y2K. It was on New Year’s Eve 2018, and that night he went a little too hard. “I woke up hungover, and the idea just came to me,” he says. “I feel like I’ve always had a vague interest in Y2K because it was such a disappointment.”
If you’re too young to remember America’s mood in late 1999: There was a fear that because some computer programs couldn’t properly process calendar information, the world’s most essential electronic infrastructures would go haywire at the turn of the 21st century. In other words, digital Armageddon. The president even felt the need to reassure the country that it wasn’t about to fall apart. “We have completed work on more than 99 percent of all mission critical computer systems,” Bill Clinton said that November. “Which means the American people can have full faith that everything from air traffic control systems to Social Security payment systems will continue to work exactly as they should.”
On January 1, 2000, there were no catastrophes. Exactly 19 years later, Mooney began to wonder what would’ve happened if hell had broken loose. So he hit up Winter. “There was just a single-sentence text from Kyle that was like, ‘Got this idea,’” he says. Mooney then explained his premise. “I was very groggy and thought, ‘That’s a good idea,’” Winter adds. “And passed out.”
Soon after that, Mooney and Winter started working on the script. While writing, they batted around hundreds of late-’90s pop culture references. “There was a test of ‘Do you remember this?’” Mooney says. “If we both remembered it and it was meaningful in some way, it got to make it to the next round.”
Dozens made it into the screenplay. Some were obvious (Abercrombie & Fitch–wrapped jocks), some were subtle (Herbal Essences shampoo), and some were inspired (Fred Durst plays himself). “In a way, the movie hinged on him being in it,” Mooney says of the Limp Bizkit frontman. “We could have come up with somebody else, maybe, but even in the few times where we tried to pitch on who that person was, nobody hit as hard or felt as right as him. The fact that it worked out was truly exhilarating.”
For research, Mooney scoured eBay for high school yearbooks from 1999. He also searched YouTube for video yearbooks from that time. “You’re scrubbing through 60 minutes of some high school in Iowa to screen grab a look,” he says.
Mooney, of course, knew what to look for. He wasn’t just familiar with the types of kids he and Winter wrote into the movie—the likable party animal; the sweet, nerdy guy; the skater bro; the underground rap fan—he was a mix of all of them. “Evan said this, so I don’t feel super braggadocious to say it myself,” Mooney says, “but any of these characters I feel like I could in theory perform if I was the right age.”
As far back as he can remember, Mooney has been a pop culture connoisseur. Growing up, he discovered Star Wars, He-Man, and Transformers via the action figures his two older brothers left around their house in San Diego. When he was young, he idolized George Lucas and Jim Henson. “I really loved that these people made massive universes,” he says.
Mooney practically studied ABC’s TGIF and Saved by the Bell, absorbing all the cheesy tropes that family-friendly TV shows used to lean on. “That style of sitcom writing and performing and general aesthetic is pretty embedded in my brain,” he says, “and something I constantly pull from.”
By the time he reached middle school, Mooney’s siblings had introduced him to Saturday Night Live and Billy Madison. His mother, Linda Kozub, also steered him toward comedy. She was the first female sports reporter at The San Diego Union-Tribune, and according to Mooney, she had a big personality. “My mom was so funny. And weird! In the best way,” he says. “For my brothers and I growing up, it could be embarrassing at times, because she could be so loud and off-the-wall. But she really made everyone laugh and was so incredibly smart. And intuitive.” Kozub died in 2023. When her son was on SNL, she appeared in three Mother’s Day episodes. “And killed every time,” Mooney says. “Everyone loved her.”
As a teenager, Mooney realized he could make his friends laugh. It was the ’90s, so a Chris Farley phase was obligatory. “Just repeating Tommy Boy lines,” he says. In eighth grade, he and a pal got their hands on a camcorder and started making mini-movies. One was a Cops rip-off called Bounty Hunters. “We’d have kids over and show them,” he says, “and they loved them.” It was the first in a long line of strange and hypnotic Mooney-made videos.
In high school, Mooney branched out as a performer. He played Prospero in Shakespeare’s The Tempest and got really into underground hip-hop. After listening to the Pharcyde, Hieroglyphics, and Freestyle Fellowship, he formed his own rap group. He’s not too eager to reveal the name of it, but he will if you ask politely: Instruments of Intelligence.
Alas, not long after Mooney headed off to USC film school in 2003, his dream of a music career ended in a way that was just a little too on the nose for him. “My dad’s house burned down, and with it all my records and gear,” he says. A week after the fire, he auditioned for Commedus Interruptus, his college’s improv troupe. From then on, he adds, “I feel like I just started focusing on comedy.”
In those days, Mooney used to spontaneously break into a character called Beer Bot at parties. “He would need a beer to survive,” Bennett says. Everyone thought it was hilarious. As long as Bennett has known him, Mooney has had a knack for bringing people together. “He was the glue of a good night,” Bennett says. “Even when he’s not making something, he’s still creating that hang. Everybody gets to benefit from it.”
As a student, Mooney enjoyed making movies with his friends. Bennett recalls his buddy entering an Ed Wood Film Festival with a short that twisted the contest’s prompt—“Rebel Without a Bra”—into a story about two surfer dudes. “Bra as in ‘bro,’” Bennett explains.
Mooney’s work was funny, but back then there wasn’t a place where he could easily showcase it. Or find the kind of archival footage that he loved. Then, in 2005, YouTube came along, and down the rabbit hole he went. He remembers devouring seemingly every single viral video from the decade: Eric Fensler’s parody G.I. Joe PSAs, Grape Lady, Halloween Punch. Bennett says that Mooney has always had a way of pinpointing exactly when a video is at its most uncomfortable. “I see him light up when he sees a specifically cringe moment. I think that is really energizing to him.”
Mooney loved moments like that, but not because he wanted to make fun of the people unwittingly responsible for them. He found them relatable. For example, the 2005 clip of a bewildered student sportscaster trying out the catchphrase “boom goes the dynamite.” Mooney thought it was hysterical and kind of profound. It was, he says, “pretty earth-shattering.” After all, he’s experienced performance anxiety, too. He really felt for the poor guy.
Finding that kind of extreme vulnerability and awkwardness online, and then re-creating it on camera, became Mooney’s obsession. “It was the fully random people on YouTube talking to an audience of like 10 people that really spoke to me,” he says. “Or people replying to more popular videos with their own videos. It was all very lo-fi and super intimate and inspired a lot of the vibe of the stuff we wanted to make early on. Most of those early videos from YouTube are gone, which I think is pretty sad, because it was such a good snapshot of mid-aughts existence.”
Fortunately for Mooney, making funny videos turned into a job right around the time he got out of college. That was 2007, two years after the Lonely Island’s pretaped “Lazy Sunday” aired on Saturday Night Live and went viral. NBC forced YouTube to take down unauthorized copies of it, but not before they’d piled up millions of views. “It was cool to see,” Mooney says. “Lonely Island had an internet presence before SNL, and then they got on SNL. It was a road map of sorts. Like, ‘Oh, this can actually happen.’”
The internet was finally a place where comedians could get discovered. Or at least try to. So after graduating, Mooney and three USC friends formed a comedy group: Good Neighbor. Dave McCary was a talented director, Nick Rutherford could write, Bennett was a natural actor, and Mooney was a relentless creative type. “For our posters and our website, he was drawing little creatures, in his childlike way creating our aesthetic,” Bennett says. “He has that type of thing where his creating goes beyond just one category.”
At first, the goal was to tour the country and put on live sketch shows. But then they started making videos. “That became the thing, it was clear, that we should focus on,” Mooney says. “Because some of them would gain traction.”
In one of those, “Unbelievable Dinner,” Mooney pretends to cook a gluttonous meal. It remains imaginary until an annoyed Rutherford starts to “believe” it into existence—kind of like how an old Peter Pan learns how to fly again in Steven Spielberg’s Hook. (John Williams’s score makes a cameo in the sketch.) The director’s daughter passed along the 2008 clip to her father, who found it funny enough to send the guys a complimentary email. “We obsessed over how we would reply,” Rutherford said later. “We settled on something like: ‘Thanks Steven. We’ve been watching your stuff too. Seems like you are on the right track. Keep making videos.’”
Like Spielberg, Good Neighbor kept making videos. Some of Mooney’s characters back then felt like versions of people he knew, or versions of himself. There was the most annoying kind of sports fan you know, who incoherently whined in a high-pitched voice about the “Benjals.” There was Todd, a walking flat-brim hat who hosted the garage-set public-access talk show Inside SoCal. And then there was the goateed Chris Fitzpatrick, who smoked cigarettes, wore clothes five sizes too big, and loved to talk shit—but was really a mama’s boy. When Chris made his debut in 2011, strangers seemed to connect with him. “People would be like, ‘Oh, I know that dude,’” Mooney recalls. “There was apparently one of those guys at every high school.”
In 2012, Mooney auditioned for Saturday Night Live. It didn’t go very well. “I tried to do the standard five impressions,” he says. “And my impressions are not good.” He didn’t get the gig. But the next year, he got another shot. The second time around, he changed his approach. “I doubled down on my voice and my type of characters,” he says, “and assumed and hoped that if I was going to get it, it’d be from doing me.” His assumption was correct. In 2013, he and Bennett both joined the cast. (Over the next few years, McCary and Rutherford also worked at the show.)
Mooney brought several of his own ideas to 30 Rock. Chris Fitzpatrick, Todd, and Bruce Chandling all got their own recurring SNL sketches. Mooney enjoyed shoving his alter egos in front of a national audience. “It goes back to the notion of ‘I haven’t necessarily seen that on TV or in a movie,’” Mooney says. Dudes like those—deeply unsure of themselves and/or full of unearned confidence—became Mooney’s bread and butter. “He would never say this, but I think he has had a pretty heavy impact on a lot of internet humor since he’s come to prominence,” Winter says. “He knows how to draw out silences and knows how to stammer to really incredibly funny effect. He observes the world in real life and he homes in on things, very specific encounters or moments that he can analyze in an incredibly unique way, that then turn into really funny characters, sketches, scripts, all of it.”
Occasionally, Mooney’s sense of humor was a bit too specific for SNL. Over the years, he appeared in several oddly memorable sketches that ended up being cut for time—which, among comedy nerds, is a genuine badge of honor.
In 2015, Mooney starred as a Steve Urkel–esque nerd in a painstakingly faithful, deadpan parody of a very special early ’90s sitcom episode. At the end of the sketch, host Ryan Gosling’s character abruptly dies in a drunk driving accident.
Before the show, Mooney was excited about the bit. “We were laughing really hard at it. It felt good,” he says. But at dress rehearsal, it bombed. “It’s a humbling experience,” he adds. “Because when something doesn’t get a reaction, you really start to see the cracks in it in the moment and realize that maybe it’s not as universal as you imagined.”
“Cool” didn’t make the broadcast, but it lives on in the place where you can find the kinds of old clips that inspired it.
Mooney was still at Saturday Night Live when he and Winter finished writing their Y2K script. “But then the pandemic hit,” Mooney says, “and I think the future of the industry was in question. So we regrouped.” They started pitching the movie to executives over Zoom. Christopher Storer, the creator of The Bear, came on as a producer. So did Jonah Hill. And A24 soon agreed to join the New Year’s Eve party, giving the movie the green light.
In 2023, a year after Mooney left SNL, he started shooting Y2K in New Jersey. It was technically an independent film, but it was by far the biggest project he’d ever been in charge of. “We were trying to make something that felt like a big-budget movie from 1998,” he says.
To capture that feeling, production designer Jason Singleton pretty much re-created an American suburb from the late ’90s. There’s even a fully built video store, complete with a Mystery Men cardboard standee and a porn room that you could get to only by walking through a beaded curtain. It helped that director of photography Bill Pope shot both The Matrix and Clueless. Mooney, uncoincidentally, cast Alicia Silverstone as the main character’s mom. “I asked her about the Aerosmith videos,” he says. “That was probably the first thing on my mind. She gave me some gossip. I can’t share.”
Picking out music for the film was both fun and exhausting. At one point, Mooney says, it felt like he and Winter discussed “truly every song that ever played on the radio between ’97, ’98, and ’99.”
Mooney basically served as an aux cord between the CD collection in his brain and the cast. Before filming, the actors each got a goodie bag with a Discman and freshly burned late-’90s mix. Dennison, who’s from New Zealand, listened to the “Thong Song” too many times. Just like Mooney did. “You could tell that it was kind of a biopic of his childhood and the way he grew up, what he watched, what he listened to, and the experiences he had,” says Dennison, who’s had roles in Godzilla Vs. Kong and Deadpool 2. “Even talking to him, like, ‘Hey, how does a Kiwi kid end up in America in 1999?’ And Kyle would be like, ‘Bro, I had French people at my high school.’ Or ‘I had a Brazilian dude who worked at the pizza place.’”
Jaeden Martell, who plays Danny’s best friend, Eli, in the movie, admits that he had a hard time separating the real Mooney from his on-screen persona. “A lot of times, he’s joking and doing bits with you,” says Martell, who played Bill Denbrough in the It reboot, “but he’s doing the same characters that he’s always done. And the line is very blurred.”
“We’re shooting in this house and it’s really hot and there’s a hundred other extras, and you’re covered in blood and there’s all these things happening,” Dennison adds. “And then he just comes on and starts laughing and having a joke with you. And it really captures his energy.”
For Mooney, that’s nothing new. He’s been this way since before Martell, 21, and Dennison, 22, were born. “When you were a teenager in the ’90s and early 2000s, you’d go off and you’d shoot stuff on the camcorder with your friends and you’d make little skits,” Winter says. “Or you’d just film yourselves hanging out in a bedroom. The intent was to pass the time and to mess around.”
At its heart, Y2K is a supercharged extension of that pursuit. “Kyle, he’s kind of always been doing that, no matter what,” Bennett says. “This type of thing, it doesn’t rattle him.”
Mooney’s hoping young people will flock to cineplexes to see his comedy, just like it’s actually 1999. But even if they don’t, it won’t stop him from doing what he does best: making stuff. “There’s always more dream left,” he says. “You know what I mean?”