Kieran Culkin sounds like he’s on mile twelve of a marathon, but he’s been running for only two minutes. We’re sprinting toward a ferry dock on the Manhattan side of the East River. As the boat we’re trying to catch pulls into view, he pushes faster still. With each step, a lock of wispy hair bounces above the crown of his head like a metronome. Fists balled, arms pumping, he looks like he’s about to hit his stride just as we arrive and get in line. He doubles over, greedily sucking oxygen. His face flushes as if he’s been slapped. “I’m feeling”—inhale—“muscles”—inhale—“I didn’t know I could access,” he manages. He gulps a few more breaths, stiffens, starts hacking. “Hot phlegm!”
We board the boat. I follow him through the main cabin, out to the rear deck, up a flight of metal stairs, and over to a pair of seats that look off the port side, toward Manhattan. Six months ago, “I turned forty and everything changed,” he says, now recovered. “Get a little paper cut on my finger; nine days later, why do I still have a paper cut? It’s just fucking slow now.”
But also, he hasn’t exercised regularly, or maybe at all, in five years, since before the premiere of Succession, HBO’s black dramedy about the excessively rich and comically power-thirsty Roy family, owners of a fictional global media behemoth. Culkin plays Roman, who’s potentially the heir to his father, Logan, as head of the empire. The show skewers the 1 percent while assuring us that for all their wealth, the Roys are no happier or less foible-prone than the plebes. It’s rich-person schadenfreude. “Watching you people melt down is the most deeply satisfying activity on planet earth,” a daughter of another dynastic family says to one of the Roys in the show’s second season.
But on a deeper, or at least more emotionally resonant level, it’s a story about family and the struggle to live up to your own legacy. Culkin, of course, knows firsthand what it’s like to grow up in a family under public scrutiny.
The ferry rumbles into motion. It’s an evening in early March, and we’re roaming. A few hours ago, Culkin texted me, “Want to take a very cold ride to I don’t know where?” This is where he comes to process, to seek solace, to clear his head—a ritual he began after his cat Leo died, in 2016, just weeks before shooting the Succession pilot. He says he finds it easier to think about his possibility-filled future when he’s floating along the river rather than sitting around at home. “Sometimes you can’t see it, and then I’m out here and I’m like, Oh, yeah, there’s stuff,” he says. “There are things I can do.”
It’s been four days since he returned from filming the final scenes of the fourth season of Succession, which its creator, Jesse Armstrong, recently announced will be its last. It marks the end of a transformative time for Culkin. Over his six years on the show, he’s become a father; bought his first place, in Greenpoint, Brooklyn; and moved from the island he’d lived on for his entire life. The show has raised his profile and his reputation. He’s received two Emmy and three Golden Globe nominations; last year, he won a Critics Choice Award. “There cannot be a better job on the planet for an actor,” he says. It’s also given him plenty of options. But at the moment, none of them are as enticing as being at home with his wife and kids.
For a guy who’s always been ambivalent about acting as a career but at the same time revels in the work itself, this is a tough situation. “I haven’t had a fucking moment to think about how I feel about it. All I know is I feel kind of down,” Culkin says. “It’s hard to sort of accept. What are the stages of grief? I don’t know which one I’m in right now. Maybe depression or denial. Maybe a little bit of both.”
We head south. Culkin gazes on Manhattan: the spires of towering skyscrapers drilled into the bedrock of midtown, the long, low swoop of neighborhoods on the island’s eastern flank, the rabbit warren of the Financial District at the southern tip, all haloed by the fading sunlight. “Sometimes I kind of hate living here,” he says almost wistfully. “But then I’ll see this and I’ll go, Yeah, this is it. This is where I live.”
The ferry tacks across the choppy water to Greenpoint, where Culkin and his wife, Jazz Charton, bought an apartment a little over a year ago. When they were considering where to move, he thought about looking outside the city. But “the idea of having a house and cars and trying to figure out the school system and how to commute—that is very easy for most, I’m assuming, but I can’t do that.”
He plays with his jewelry as he talks. On his left hand, he wears a wedding band—he and Charton eloped ten years ago in Iowa, midway through a road trip across the country—and two signet rings, each engraved with an initial, one for their three-year-old daughter and the other for their son, who’s nearly two. There’s also a Rolex he bought when he finished shooting the first season of Succession. He got one for Charton, too, a not-so-small indulgence to remind them of a remarkable moment. On his right wrist, he wears a couple bracelets (one made of beads that spells his son’s name, the other snagged from Roman’s wardrobe) and a bandanna that his daughter wore on her head as an infant for sun protection. It reminds Culkin of a time, not long ago, when she was that tiny.
We follow the ribbon of the river around the bulge of land that marks the northern edge of the East Village. Culkin began hanging out there in the early 2000s, visiting his older brother by two years, Macaulay, whom he calls Mack. At the time, Culkin was a teenager, still living at home on the Upper West Side; he’d lace up his Rollerblades, pop a John Frusciante CD into his Discman, slide it into his gigantic jeans pocket, and race downtown. He moved to the East Village himself a year later—not to be closer to his brother but because he found a place he could afford that contained the one fantasy feature he requested. “I know it’s a stupid thing,” he says, “but I wanted a sunken living room.”
He lived in that apartment for nearly twenty years. Learned to be an adult there and, once he and Charton were married, how to care and be cared for. But then they had one kid followed by another, and one day he woke up and felt like his family was living in the apartment of a “nineteen-year-old who doesn’t know how to do the dishes himself yet.” So they left. Culkin isn’t ready to give it up, though, so he still pays the rent and uses the place as an office. Sentimental? For sure. Practical? Absolutely not.
Before their family name became famous, the Culkins lived eighty blocks north of here, in a railroad apartment in Yorkville. Kieran and his six siblings—they were a unit. He liked to count them off one by one as they entered the front door, and he didn’t fall asleep until after they’d all drifted off. They lay close enough in one cramped room for him to know: on the bottom of one bunk bed, Kieran and Mack; above them, the oldest, Shane; on the bottom of a second bunk bed, Quinn and Chris, kids number five and six; above them, Dakota, who went by Cody, the second oldest; and baby Rory in the crib.
All seven siblings tried their hand at acting at the encouragement of their father, but only Mack, Kieran, and Rory pursued it seriously. Of course, Mack broke through first, in 1990, with Home Alone. At ten, he became the most famous child actor in the world since Shirley Temple. “Poor fucking guy,” Culkin says of his brother. “He was little and having to try to accept that level of fame as reality.” At home, things remained relatively normal. It was the same at school. But the reminders of just how famous Mack had grown—the nosy people at the next table, the cabdriver who followed them home, the hangs at Michael Jackson’s Neverland Ranch—became unavoidable. “Even at that time, as a kid, I remember thinking, That sucks for him.”
It sucked for the whole family. Paparazzi trailed them everywhere. News outlets reveled in any signs of familial discord, particularly during his parents’ bitter divorce. In 1995, Kieran, then thirteen, handwrote a note to the court requesting to bar the media from covering their custody fight. “Your Honor,” he wrote, “I ask you please to spare my family any further embarrassment by letting the press in the courtroom. It has already been hard on us and I see no point to it.” A judge denied the plea and allowed the reporters in. To this day, Culkin refuses to talk to Access Hollywood, because, he says, “they did a whole piece on my family in 1997.” Ditto with the New York Post, the outlet that taught him “the newspaper doesn’t always give you the facts.” He pauses. “Let me rephrase that. The New York Post doesn’t always give you the fucking facts.” But sometimes on the carpet, the outlets get to him, anyway. “They don’t always tell you who you’re talking to until after you’ve talked to them,” he says. “ ‘Who is that by the way?’ They’re like, ‘Access Hollywood.’ ‘Fuck! Just broke my own fucking rule.’ ” For years he’s been holding on to a dusty bag of a dozen or so 8mm home movies from his childhood, hesitant to hire someone to convert them because of the potential for a leak.
Despite the turmoil, Culkin never considered giving up on acting. He attended Catholic school through third grade—“Ms. Skippington loved tiger lilies, Ms. Grundy was mean, and Sister Joselita died while she was teaching my class,” he says—before transferring to the hilariously named Professional Children’s School. “Like, if you needed a child for hire, I’d show up with a briefcase: ‘Hi, ma’am, my name is Kieran. I’m here for the weekend,’ ” he says. Really, the school specialized in working around the busy schedules of kids in the performing arts. And his was especially busy: Father of the Bride and its sequel; The Cider House Rules; the Freddie Prinze Jr. vehicle She’s All That. Or, in Culkin’s words, “Blah blah, some shitty movies nobody saw, doesn’t matter.” Acting was something that, as a Culkin, you just did. Nothing odd about it.
That is, until he landed his first breakthrough role, in Igby Goes Down (2002). The movie didn’t ignite the box office, but his wry performance inspired headlines like “Macaulay’s Little Brother Grows Up at Last.” Suddenly people were starting to talk about his career. “I heard that word and flipped out,” Culkin says. He knew well the damage unwanted attention could bring. “I had this unhealthy relationship with what I did for a living. I really wanted to do it, but I didn’t want to be successful at it.” He’d skipped a lot of crucial stages of adolescence to work. So just as his career was about to take off, he stepped back to sew up some loose stitches. “I can relate to that flinching,” says his Igby costar Claire Danes. “I experienced a version of it myself. It’s really daunting to be on the edge of your adult self and suddenly have a lot of attention and opportunity and not be entirely sure how to focus it.”
Danes hung out with Kieran and Mack back then. “They’re such nice guys,” she says. “That sounds dismissive—I don’t mean it to. I’m always thrilled by people who are genuinely unassuming, especially people who have gone through as much as they have.” They were, she says, “very protective of each other.” The siblings all looked alike. Still do: At a recent photo shoot, the photographer showed Culkin a previous photo as an example of the vibe he wanted. He thought he had pulled one of Kieran. Culkin glanced at it. “That’s cool,” he said, “but that’s not me.” It was his younger brother Rory.
Still, the family unit has diffused. They’ve grown older and grown apart—not on purpose, but that doesn’t make it any easier.
In 2008, Culkin’s older sister, Cody, died after getting hit by a car. She was thirty. He says that of all his siblings, Cody is the one who reminds him most of Roman Roy. Definitely when it comes to humor and the ability to cut people down. “The only difference is that she wouldn’t do it in a big group,” he says. “Not because she was kindhearted but because she was shy.” A word or phrase they associate with Cody is all it takes for the Culkins to crack up.
Every year on her birthday, Culkin visits her grave, north of New York City. This year, for the first time, he went with his daughter. They brought a blanket to lie on, and snacks and a ball, and they had a lovely day with Aunt Cody.
While Succession covers a ton of thematic ground about the privileged—entitlement, power, wealth—the show isn’t about money so much as it is about family. And at the beginning of season 4, which premiered on March 26, the Roy family is more splintered than ever.
As always, Connor, the oldest and least likely scion, is needed nowhere and by no one, so he directs his energies into projects that he thinks may finally make his father proud, like running for president. Of the three remaining Roys, each one has seemed, at times, the kid most likely to succeed their father, only to falter. Season 1 went to Kendall, the second oldest, who is so entitled, his identity so entwined with taking over from his father, that he risks psychic death if he doesn’t get to become king. Season 2 was Shiv’s, the baby and the one most like their father. But she’s a steamroller—she lacks tact, discretion, and the sense of when it’s time to shut up. Culkin’s Roman is puckish and obscene but also the classic middle child, overlooked and battling to stay relevant in family affairs. By season 3, he seemed to have figured it out and not fallen prey to the same self-immolating tendencies as his siblings. Then, whoops, he sent a dick pick to his dad.
Just before they shot the Succession pilot, around the time Culkin discovered the therapeutic benefits of the ferry, he had no idea how successful the show would become, or how much praise he’d receive. There was no sign it would even get picked up. So he tried not to overthink it and chose just one trait for his character. He says he decided that Roman would feel “like he never has to suffer any consequences. He can literally walk in any room and throw a drink in some lady’s face, and it’s fun.”
His performance had a huge impact on the show from the beginning. Jesse Armstrong, Succession’s creator, says Culkin was the first person he cast: “There’s a certain way in which he was so tonally on that it gave me the confidence that we were in the right area for the tone of the show.” From the first moment Roman appears, greeting a roomful of suits (“Hey, hey, motherfuckers”), Armstrong says, “there wasn’t a cigarette paper between my vision of the character and him. I couldn’t even remember what I thought that guy would be before Kieran did it.”
Before Succession, Culkin didn’t have much experience with improvisation. While filming the pilot, director Adam McKay shouted from behind the camera to Alan Ruck, who plays Connor, to toss out a few lines from the top of his head. “It kind of horrified Kieran,” Ruck says. “He was like, ‘I like writers to write my lines. I like to say them, and then I like to go home.’ ” But between then and the shoot for the second episode, something clicked for Culkin, Ruck says. “He turned into an artesian well of snappy bullshit.”
Culkin’s newfound comfort with improv helped inspire one of the more memorable dynamics on the show: the taboo, non-physical, semi-kinky flirtation between Roman and Gerri Kellman, in-house counsel for his father’s company and a couple decades his senior. After witnessing a brief, charged glance between the two characters in the first season, the show’s writers channeled an already developed story line about Roman’s sexual dysfunction into this relationship. What makes it all the funnier is that Culkin and J. Smith-Cameron, who plays Gerri, have been friends for years. “We were kind of always flirting on set,” Smith-Cameron says. “It was never for one second a real flirtation. It was that set-crush kind of thing.”
In lesser hands, Roman could’ve been played for pure comedy. He’s arguably the funniest character on the show. But Culkin elevated the role to tragicomedy by not just milking the lines for laughs. It’s never simply about the punchline; there’s an underlying pain that lurks but never fully breaches the surface of Roman’s ego. “He embodies the moral decay of the show,” says Alexander Skarsgård, whose billionaire tech CEO character, Lukas Matsson, first appeared in the third season and continues in the fourth, “and how fucked-up they all are.”
Fucked-up but still family. Last year, the cast traveled to Los Angeles for the Emmys. At the Sunset Tower, Nicholas Braun, who plays cousin Greg, turned to Sarah Snook, who plays Shiv, and said that he doubted they’d ever be cast together again, because everyone would think of them as cousins. Just then, Culkin walked up and asked what they were talking about. What Snook did next, she tells me, “is probably indicative of the very sibling relationship that Kieran and I have offscreen as well.” It’s something she imagines Culkin would’ve done to her had the roles been reversed: She rubbed it in his face. “Hey, Kieran, you’ll love this,” she remembers saying. “When we finish this show, you and I will never work together again.”
It was in keeping with their usual banter, but the kernel of truth gutted him. “I went, ‘Why the fuck would you say that? Fuck, I want to cry,’ ” Culkin says. (“It hit him much more than I thought it would,” Snook admits.) For the first time, they collectively considered that Succession would end, though they didn’t know when.
Even when the fourth season began filming in June 2022, the cast and crew were unsure whether it would be the last. The general vibe was This may be the end—unless it isn’t. The moment Culkin accepted that the show was ending was at this past January’s table read for the last episode of season 4. Armstrong said it in no uncertain terms: “So this is it.” And then…he continued. “Unless it isn’t. There’s still maybe…”
“I laughed,” Culkin says. “Fucking come on, man. Is it the end or not? Stop telling me you don’t want to be with me but that you still sort of love me.”
But by the time Armstrong finished speaking, he’d essentially settled the matter definitively. Everyone reacted in their own way. Snook lost it and couldn’t really talk to anyone. Matthew Macfadyen, who plays Shiv’s husband, Tom, got choked up, but his response was similar to Culkin’s: At least we have an answer. I can accept that. “I think Brian [Cox, who plays patriarch Logan Roy] had mixed feelings about it, too,” Culkin says. “He was more like, ‘Well, good, we’ve done it.’ But I bet if you said, ‘Would you like a fifth?’ he’d want to.” Of course, that would’ve depended on where the plot of season 4 takes the Roys. Who’s to say they’d all still be alive?
As with any family, strains sometimes sprang up between the cast members. A couple years ago, in a New Yorker profile of Jeremy Strong (aka Kendall Roy) that detailed the sharper edges of his role prep, Culkin was critical of his colleague. I ask Culkin if he and Strong ever discussed the article, or if it affected their working relationship. He doesn’t really answer. “We’re professionals. We like to go to work and do the thing. I don’t think it affected the way he did his work at all. Wouldn’t have affected mine. I think it was fine.” His measured answer hints there’s more to the story, but Culkin seems to have learned to keep familial criticism to himself.
Besides, he says, the occasional tension never got in the way of the work; sometimes it brought the cast closer together. He will miss Cox’s onset “outbursts,” as Culkin calls them, none of which he can quote, “because they will definitely be misinterpreted. If you were a court stenographer in the corner of our set…” He leaves it at “It’s just so funny to see him lose his shit.” Culkin learned that Cox would calm down with a sugar boost, so he’d tell the production assistant to keep a sandwich or a banana nearby. If they didn’t heed his advice on the first day, they did by the second. Cox would begrudgingly accept the craft-services offering, eat it, and calm down.
Culkin will miss these people. He’ll stay in touch with Smith-Cameron, for sure. But everyone else? “I’m not really going to keep up a proper relationship with anybody just because of logistics,” he says with a hint of anguish. He says that Macfadyen lives in London. Braun is bicoastal, yet mostly in Los Angeles. Ruck is in L.A., too. Strong splits his time between Copenhagen and New York but calls Denmark home. Snook is in Australia. Cox, he lives all over the place. “It’s a big, big loss.”
During a break in the filming of the final episode, Culkin, in character as Roman, came up to Ruck, still in character as Connor, and started talking about erections, then asked if he could still get one. “With a little help, yeah,” Ruck replied. Culkin cracked up, then hugged him. “Kieran said, ‘I’m really going to miss you,’ ” Ruck tells me. “The feeling is mutual. I never had a little brother, and if I could have a little brother, I’d want him to be exactly like Kieran.”
The goodbyes were done in waves. On the wrap day for Ruck and Justine Lupe, who plays Connor’s wife, Willa, everyone was getting weepy, so Ruck began to speak. “I’m going to teach you the Roy family toast,” he said. “Here’s to you, and here’s to me / The best of friends we’ll always be / But if someday we disagree / Fuck off.”
The ferry docks at the last stop, Wall Street. We disembark, duck into one of the oldest bars in New York, and settle in to discuss Culkin’s future over pints of lager.
Some actors can’t help but sacrifice themselves on the altar of art. Culkin is not one of those actors. Well, not exactly. “It’s a fucking job,” he says, but “it isn’t just a job, either.” There’s a feeling—he doesn’t say fire or passion because he’d feel like a pretentious asshole, so he calls it “that thing in the ol’ tum-tums”—that kicks in while he’s working, driving him to give it his all. But also, he says, “Not having a job? Lovely.”
So far he’s signed on for just one new post-Succession project, Jesse Eisenberg’s sophomore directorial effort, A Real Pain, a contemporary Holocaust movie set partly in Poland. Culkin is anxious about being away from his family on set for an extended period once again. “There’s no reason for me to do it, except I feel like, creatively, I want to,” he says. “And that sucks, because now I feel like I’ve got to do it.”
After A Real Pain and a few voice-over jobs he’s been kicking down the road for months, he’s not sure what’s next. The scripts he’s been reading don’t interest him. He’s contemplated working on a project of his own, but it’s too early for him to share even the barest of details. He sips his beer. “I would like there to be nothing for a little while,” he says.
What really interests Culkin is family. Not the Hollywood version of what family is, but actual family. Almost every story he shares somehow comes back to his wife and children, revealing the minutiae of their lives almost like tiny prayers of gratitude. “I feel like what I’m supposed to do is be a stay-at-home dad,” he says at one point. “That’s where I feel like I’m the most me. And anything that takes me away from that is wrong.”
Once we finish our lagers, he asks if we can meet up with Charton. They’ve hired a sitter for the night, and she’s out with a friend. As we walk back to the ferry, he winces. “I’m going to be sore tomorrow,” he says. We meet up with them at a restaurant in Greenpoint, where they’re holding court as the servers close up for the night. Over a nightcap, we talk about the kids—her friend has a child at the same school as their daughter—but this time Culkin is quiet. He looks ready for bed. He just gazes at his wife with love and a little relief.
Asmall group of cast and crew went on a final weeklong trip to film the last scenes of the final episode of Succession. It was like an upscale sleepaway camp. Everyone ate meals together; they milled around in between shots, shooting the shit. They mostly were working nights, and Culkin turned a bit vampiric. At the end of the night, when they’d finish, he and Snook would go to the screening room to watch cartoons. They all did their best to tuck away their sadness and focus on the work, which wasn’t always easy. On their second day away, Armstrong publicly announced that the show would be ending for good.
Mark Mylod, who directed the series finale and at least a third of all the Succession episodes, more than any other director, would typically give a short speech to the actors once he called wrap on an episode shoot. But after they finished that very last scene, everyone gathered around Culkin, Snook, and Strong and spontaneously erupted in applause. They clapped for ten minutes.
When it eventually quieted down, Culkin gave a speech of his own. Without any Romanesque impishness or casual ribbing, dropping all pretense, he addressed the family he was losing. He mostly talked about Sarah Snook— thanking her for their years together as costars; sharing that she’s one of his favorite people on the planet and one of his favorite scene partners. That she’s the perfect person to bounce the ball off of, that they can go into a scene not knowing what they’re going to say and know they’ll figure it out along the way together. That it’s just easy. And he spoke of his fear that they would never be cast together again.
Snook had been right: Given the chance to deliver this news, Culkin took it. He just did it in a way that broke everyone’s heart.
At the wrap party, there was karaoke, and Snook and Culkin sang an inspired rendition of the B-52s’ “Love Shack.” Mylod says he sounded like a deranged version of frontman Fred Schneider. It was both a parody and an homage, unsettling and borderline scary—and so fucking funny.
On the flight home, after everyone had drinks in hand, Mylod turned around to Culkin out of the blue and asked if he’d ever consider doing an action movie. The director had been thinking about what his next project might be and imagining how he might shake up the action genre. “I thought, Who would be a really surprising person to drop in the shit and try to watch them survive?” Mylod tells me. “And I’d really like to watch Kieran do that.”
Culkin, whose slight frame hardly screams superhero, replied that he would be game so long as he could get the shit kicked out of him—the action hero who can’t fight. The idea makes you smile, doesn’t it?
“A few years ago, I would have been like, ‘No, I’m not going to do that, because I can’t. Who the fuck would buy that a 140-pound, five-foot-seven guy could start kicking some ass?’ ” Then again, you never know. “But now there’s a reality where maybe…” he says, trailing off. The idea needs to be good enough to take him away from his family. But there’s a chance. That’s what Succession did for Culkin: Where once he saw barriers and dismissed opportunities, now he sees possibilities. He can do stuff.
This story originally appeared on Esquire U.S.
Story: Eric Sullivan
Photos: Billy Kidd
Styling: Andrew Mukamal
Grooming: Benjamin Thigpen
Creative Direction: Nick Sullivan
Design Direction: Rockwell Harwood
Visuals Direction: James Morris
Executive Director, Entertainment: Randi Peck