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I’m waiting for Kieran Culkin at the tip of the Greenpoint ferry platform, where he’s suggested we meet on a Friday morning to get on the boat, take it a few stops to Dumbo, then walk across the Brooklyn Bridge into Manhattan — a sort of hung-over New Yorker’s triathlon. He’s late and sending me self-effacing riffs about it: “I was just about to text you to see if you were also running late or if you were the kind of person that was professional and an actual adult, unlike myself.” The ferry pulls into the dock at the exact moment that I spot him on the horizon. He is instantly recognizable, clad in all black and wearing a pair of sunglasses, eyebrows perma-arched, hair like an inverted comma, walking with distinct hustle but not running. The boat starts boarding right as he reaches me, a little out of breath and visibly relieved that he pulled it off. “This is what I do,” he says. “I pull up to airports, I don’t even know what airline I’m flying. Sometimes I don’t know what city I’m going to. I still get on the plane and everything’s fine.”
As we line up to show our tickets, Culkin, a lifelong New Yorker who rode the subway around the city alone by 13 and who contains all of the ungovernability and bullshit-detecting that this implies, digresses into a spontaneous but deeply felt spiel about the ferry’s flawed digital ticketing system (“The physical ticket, I can just put it in my pocket. I just have to get here early enough to go to the kiosk and fucking do it. But I’m lazy. And now I’m bitching about how lazy I am”). I will soon learn that this is his greatest talent, second only to his ability to wring humor, poignancy, and a sense of total reality from the dozens of onscreen characters he’s been playing since early childhood. Later, he will joyfully go full Larry David on everything from coffee-lid sizes to the concept of wearing shorts (“It’s a weird garment”).
Culkin, 42, has made his career portraying boys, teenagers, and now adult men not unlike himself: hyperverbose and stubborn, skin-of-their-teeth charming, effortlessly funny, irascible and self-lacerating. He’s mastered the art of playing people who think they’ve mastered the art of the carefree, loutish façade but whose pathos and pain glisten through the cracks. He uncovered that instinct as a part of the brief but powerful Culkin Child-Actor Dynasty in blazingly earnest ’90s films like The Mighty and The Cider House Rules and Father of the Bride, sharpened it as a teen in artier fare like Igby Goes Down and The Dangerous Lives of Altar Boys, and most recently and famously perfected it on HBO’s Succession as sad perverted clown Roman Roy.
He’ll next star in the film A Real Pain, a dramedy about a pair of cousins who embark on a Holocaust tour of Poland in memory of their late grandmother. Culkin is at the apex of his idiosyncratic powers as the magnetic charmer Benji, whose easy banter with his fellow tourgoers gives way to increasingly volatile moods that reveal a tormented core. Jesse Eisenberg — who wrote, directed, and stars opposite Culkin — is the ostensible protagonist David, Benji’s uptight, socially awkward cousin who envies and pities him in equal measure, but A Real Pain is Culkin’s showcase. Eisenberg remembers being consistently astonished by Culkin’s ability to show up on set with no idea which scene they were filming that day, scan his lines, then casually deliver “the greatest acting I’ve ever seen in my life.” Its Sundance and Telluride premieres received glowing reviews praising Culkin’s performance specifically, entering him into the Best Supporting Actor Oscar conversation.
And Culkin nearly dropped out of the film. He’s notoriously picky about taking jobs; he turned several of them down in the years after 2002’s Igby, unsure if he wanted what he saw as a fun childhood hobby to be a proper career. “Things were coming,” he recalls of that time, like movies written specifically for him, and “I freaked out, ran away.” He eventually got comfortable taking on more parts, only saying “yes” when he really connected with something — which is exactly what happened when he read the script for A Real Pain while filming Succession’s final season in 2022.
“It was one of the very, very, very rare scripts that I laughed out loud reading,” he says as we disembark and begin our trek toward the bridge, both sweating in the early-September sun as he curses himself for coming up with this activity and then showing up for it in an entirely black outfit. “It was that rare thing of, Oh, I know who this character is and I know how to do it.” Specifically, he recognized Benji as a near-perfect doppelgänger of someone unnamed whom he knows in real life as well as in a sort of a quantum-multiverse, Sliding Doors version of himself. “I’m one quick little misstep away from being that person,” he says, and he credits his decision to stop smoking weed in his 20s as one of the things that saved him from a lonely, depressive, Benji-esque fate. He took the role after the Real Pain producers told him the film wasn’t shooting for another year. “I’m like, ‘Oh, a year? That’s not real life.’ Then that year was up. And I had a panic.”
Culkin is a consummate wife guy who brings up his spouse of 11 and a half years, Jazz Charton, dozens of times unprompted and tells me his ideal job would be a stay-at-home dad. “Some people say that but don’t really mean it,” he says, knowing how the whole thing sounds. “And some definitely just couldn’t do that.” So he was particularly stressed by the idea of being separated from Charton and their two kids. He learned while making Succession that eight days is the maximum he can be away from them without plunging into dissociative despair. “I don’t know who I am without them,” he says. As we exited the ferry, Culkin instinctively reached to grab a stroller from the storage area. “Where are my fucking kids?!” he joked.
He tried to pull out of A Real Pain just before production began and ended up on the phone with Emma Stone, his onetime girlfriend and a producer of the film. “She did an almost reverse-psychology thing on me,” he says, laughing. “She was like, ‘Oh, I totally get that. If I were you, I’d probably feel that way.’ And I was like, ‘But have they started?’ She goes, ‘Oh, yeah. They’re actually already in Poland scouting locations; people are hired.’ I was like, ‘It’s not like people would be out of a job?’ She’s like, ‘No, no, they would, but it’s not on you. You said ‘yes,’ but if you have your reasons for not doing it, you’re not responsible for these people’s jobs. It’s fine; you do whatever you want.’ And I got off the phone and I went, ‘Ah.’ ” Stone laughs recalling the conversation. “I can’t believe he talked about it publicly,” she says. “Producing, I’ve realized now, is like parenting — every kid needs different things.” Stone got on the plane with Culkin, his wife, and their kids to make sure he made the journey. “I was so grateful that he did it, but, also, thank fucking God. Because it would’ve been catastrophic,” she says. His family was able to join him for a good chunk of the shoot but not all. When I ask how he pushed through the 25 days without them, he deadpans, “Alcohol.”
Eisenberg didn’t learn about Culkin’s attempt to back out until after the film was finished. But when Culkin eventually told him, he was relatively nonplussed. “It was just another thing in a long line of, like, Who is this person?” Eisenberg says. He cast Culkin without ever having seen him perform in anything. The two had only met briefly — once on the set of Zombieland (where Culkin was visiting Stone) and once at an audition for Adventureland, which Culkin didn’t get but Eisenberg did, and where, Culkin tells me, he made the spontaneous artistic choice to pinch Eisenberg’s nipples through his shirt as part of the audition scene and forgot to remove his hands once the director called cut. When I bring this up to Eisenberg, he pauses thoughtfully. “I had forgotten about that. That’s right,” he says. “We’ve never discussed it. I think he squeezed my breasts.” While the breast-squeezing left no lasting impression, what did was Culkin’s “magic trick” ability to project both lightness and darkness simultaneously and in equal measure. He “exhibits real quickness, but there’s also a kind of real-world heaviness to him,” Eisenberg says.
Culkin isn’t Jewish, which was a major discussion, Eisenberg says: “I have 17,000 thoughts about this, and where I come out is he gave me an amazing gift by helping to tell this story that is very personal for my family.” As Benji, Culkin is as enchanting as he is impulsive and infuriating, casually befriending other people on the tour to the astonished envy of David then later berating their sweet guide for his “constant barrage of stats.” In a vivid moment roughly midway through the film, he publicly melts down about the cognitive dissonance of traveling first class on a Polish train on a Holocaust tour, embarrassing David and baffling his peers. David in particular can’t seem to understand why Benji is so consistently plagued by suffering. “You see how people love you? You see what happens when you walk into a room?” he goes on to ask him. “I would give anything to know what that feels like, man.”
Unlike a lot of actors, who tend to try to distance themselves from their most widely known role in fear of being existentially stuck or typecast, Culkin constantly and happily steers our conversation back to Succession. The show was deeply meaningful to him — it was where he says he finally realized he wanted to be an actor. On a personal level, he was such a fan of the series that he almost always watched it with Charton as it aired each Sunday night, though he mostly avoided the internet discourse. “My wife would tell me certain things, like, ‘Oh, people are making fun of the way you sit.’ And she’ll show me on her phone. And I’m scrolling, like, ‘Oh, yeah, I sit weird in the show. I didn’t know that.’” He still hasn’t seen the final episode, in part because he was already in Poland filming A Real Pain when it aired. It’s been so long now that he and Charton are planning a rewatch going back to episode one. He admits he might also be avoiding the finale because then the whole thing will really be over. He still daydreams about a spontaneous fifth-season pickup: “There’s part of me that feels like, When are they going to call?” he says. “I think maybe the reason is because I didn’t get the closure of watching the last fucking episode.” Suddenly, we are confronted by the half-naked body of his Succession co-star Alexander Skarsgård hovering above us on a gigantic billboard. Culkin stops talking and looks up at him, beaming with pride. “Well!” he says. “There he is.”
While filming Succession, where he was encouraged to play around with his lines and his character, Culkin developed a sort of free-associative acting style, but he won’t go so far as to call it improv (“That has a certain feel to it”). Instead, he calls it blagging, British slang he picked up from his wife that loosely translates to “fake it till you make it.” He doesn’t like to talk too much about how he does this or try to analyze it; to look at it too hard might ruin the whole thing. “It’s written, and I understand the character, and then some shit comes out sometimes; that’s it. And I don’t force it,” he says.
The not-improv improv of it all caused an initial clash between Eisenberg and Culkin on the set of A Real Pain. Eisenberg is a type-A planner and had each scene carefully blocked and plotted out. Culkin felt stifled by the relative formality. “It felt a little bit like going backward,” he says. “Jesse had set up shots before I got there to be like, ‘You’re going to stand here.’ And I’m like, ‘How do you know?’ He goes, ‘Why wouldn’t you?’ I’m like, ‘Well, we haven’t tried it yet is all I’m saying.’ I tried to go along with him those first couple of days, and it felt like, Why am I hired?” Eisenberg remembers changing his mind after filming a specific scene in which he asked Culkin to run up to co-star Jennifer Grey, who plays a tourgoer who bonds with Benji, and say whatever he wanted because they weren’t going to use the audio. “He was so free and funny that I didn’t mind throwing out the blueprints.”
We’re in the East Village now, Culkin’s erstwhile neighborhood of 20-plus years, where he’s meeting up with Charton. He spots her from across the street and makes a loud birdcall to get her attention. Charton is disarming and funny, and the two are clearly enamored with each other, falling into natural repartee about their kids and each other. Charton lovingly mocks Culkin for being winded from our walk. “We went to our daughter’s school, and you’re only supposed to use the elevator for an emergency or if you have to, so we took the stairs and Kieran was out of breath at the second floor,” she says, laughing. Culkin picks up the story: “I made it to the third, and I took a break. She thought I was kidding.” Charton imitates Culkin: “‘I can feel my heart!’”
In January, Culkin got up onstage at the Emmys and informed the world that he’d like to have another baby, which Charton promised him she’d consider if he won. “She had no faith that I was going to,” he explains, shaking his head. “I didn’t have that forethought of like, What’s going to be the response to this?” It backfired somewhat. “I was very moved, No. 1,” Charton says. “And then I was very confused that he would bring up my uterus.” Culkin nods cheerfully, willing to accept notes. “That I was calling you out publicly,” he adds. “I mean, luckily he’s not super-famous or anything, but I got weird messages from friends and family about it,” Charton says. “I feel like my uterus is now public domain.” He is openly apologetic about the bad blag, and the possibility of another kid is still on the table.
Culkin’s next big project is Glengarry Glen Ross on Broadway, opposite Bob Odenkirk and Bill Burr, in the spring. He agreed to do the play because he thought it would give him more time with his family. “Then I talked to friends who do theater and have young kids, and I was like, ‘Wait, is it good?’ They’re like, ‘No, you never see your kids. You’re working every night. You never do bath time, bedtime. You get one night a week,’ ” he says. Instead of trying to get out of it, he asked the producers to change the schedule so he could have Sundays off. To his surprise, they said “yes” and moved the show to Mondays. “I’ve never heard of the show going dark on a Sunday,” he says. “Now I get one day a week dedicated to just being a dad.”
That night, he and I meet up at a Gramercy steakhouse whose interior is emblazoned with a gigantic sign that reads “Beef and Liberty,” the sort of place that the Roman Roys of the world might conspicuously snort cocaine off a leather banquette and where, across the street, the entire Lohan family is dining outside. When I ask Culkin if he knows Lindsay, he corrects me on the pronunciation of her name (LO-uhn) and says he doesn’t ever recognize any famous people except for the anchors on NY1; recently, he says, he chatted up a very important higher-up at Disney without having any idea who he was. We order dirty martinis — “Very, very, very dry, barely any vermouth” — and Culkin deliberates for a very long time about which steak to choose, asking the waiter pointed questions about its provenance before landing on a huge bone-in so he can take the rest home for his family. But later, when he asks for a to-go box, he hands it all to me, insisting on giving me the leftovers because he wants me to make a steak soup that one of his brothers once cooked for him. He takes a deep breath and begins describing the recipe for it in passionate, exacting detail.