But his spirit was not tarnished. Actors have to get used to rejection, but few metabolize it like Culkin: with a wave of joy. Frankly, he inspired me. Isn’t it fun to be rejected? We climbed into the car he’d reserved and considered our options: There was The Grill, a shrine in midtown where he filmed scenes from Succession; and The Grill, a shrine in the heart of downtown; the Bowery Meat Company, which specializes in “big barbecue,” and Keens Steakhouse, which has the world’s largest collection of steward’s pipes.
Culkin’s driver has taken many people to The Grill, and he told us the restaurant has a dress code. Culkin wore a black short-sleeved shirt and sneakers. He had a turban tied around his wrist. I wore a denim jacket and Birkenstocks. Culkin folded his hands, full of anticipation – another rejection!
We debated the merits of specific restaurants. Yelp was consulted. Interiors were compared. “I’m not a judgmental person,” Culkin told me, as the tabs on his phone mounted. Fifteen minutes later we walked into Keens.
Of course, the tendency for mild insults is one of Culkin’s quirks that he may have borrowed from Roman Roy, his playfully mercurial character in Succession. Roman was a fully committed role for Culkin, and his performance received viral enthusiasm and resounding praise. He hasn’t appeared on screen since the 2023 finale.
But here comes “True Pain,” the second feature from actor and filmmaker Jesse Eisenberg. The film, which was a hit at Sundance and will be released in theaters in November, follows Jewish-American cousins David (Eisenberg) and Benji (Culkin) as they embark on a trip to Poland to learn more about their late grandmother’s story. The trip wasn’t exactly a vacation one, but took them to the Majdanek concentration camp (where Eisenberg got permission to film), dilapidated graves and their grandmother’s hometown. The film is so self-indulgent that it seems to require a new combination – some mix of poignancy and shallowness or sharpness and shamelessness. Is there any other way to capture Benji as a Jew on a train traveling through Poland who is refusing to pay his fare?
Eisenberg sent the script to Culkin while he was filming Succession, and Culkin signed on immediately — even though he had planned to take a break after the show to spend time with his wife, Jazz Charton, and their two children (later triplets and a baby) spending time together. When filming of “Succession” began later than expected, he realized he would have to arrive in Poland earlier than expected: That was a problem for Culkin. “They’re very excited about becoming parents,” he told me as we sat in a wood-paneled booth at Keys. He considers his children his only real accomplishment, which may explain why taking care of them seems to replace all of his previous hobbies. When Charton met Culkin he was an avid indoor rock climber. After that, he stopped bouldering and started climbing on playground equipment.
Over the next three hours, Culkin will tell me about all the things that have changed since becoming a father: performing, vacations, sleeping in hotels, being recognized in public and his experience with time zones. He puts a sticker of his daughter’s swimming lessons on his phone case. (And a Keanu Reeves decal, because Chayton loves him. But “who doesn’t love Keanu?” Culkin wondered. “Let’s be honest.”)
Culkin was determined to be some kind of father, which meant he was determined to be nothing like his father. He grew up in a railroad apartment in Manhattan with six siblings — most of whom were former actors, including, of course, his older brother Macaulay — whom he called “Mac.” Kieran’s first role was in Home Alone, where he played McEvin McAllister’s cousin. He was eight years old at the time and has maintained a level of fame ever since. But the legacy he follows as a Roman in The Succession complicates matters. He and his father, Kit, don’t speak, the rift going back decades. (Over dinner, Culkin told me I seemed like a “properly grown-up” person, and there was no better compliment.)
So as the date for Culkin to leave for Warsaw to begin work on Real Pain drew near, he was talking crap. His children were old enough that he missed him – and he was terrified when he learned he wouldn’t be able to see them for a month. Actress Emma Stone, True Pain’s producer, has been close to Culkin since the two dated from 2010 to 2011. should be released on bail. Eisenberg was scouting locations in Poland; Culkin would be on set in a few weeks. But Stone told him she understood and would handle it. Culkin thought he had been replaced. No. He said, “The whole movie will be ruined if you don’t do it. But it’s not your responsibility. You shouldn’t feel that burden at all.”
Culkin was surprised by her approach. “She was nice and she got me out of a bad situation,” he said. “So I guess I’m… in?” When Stone flew to Poland, she made sure she and her husband were on the same plane. Eisenberg compared the elaborate airport trip to a hostage exchange.
Eisenberg didn’t realize how close Culkin had come to defection until “True Pain” premiered at the Sundance Film Festival. “I was furious,” Eisenberg told me. “But the more I got to know him, the more I understood that his lifestyle was completely atypical in an industry filled with eager flatterers.” Despite Culkin’s natural tendencies, he still took the job.
Both men admitted filming didn’t get off to a good start. Culkin was used to the “very, very loose” process run by “Succession” producer Jesse Armstrong. Eisenberg stopped the entire film before the rest of the cast arrived on set. The problems started within the first few hours. Eisenberg told Culkin where he should stand. Culkin thought the position was wrong. “Jesse said, ‘Well, that doesn’t feel weird,’…” Culkin said. “I was like, ‘I have to feel what I’m doing.'” This went on for about a week until Eisenberg finally gave Culkin permission to get out of his own way. “He’s very smart,” Eisenberg said. “But I still don’t understand how he thinks or works. He doesn’t know his lines, and then I’ll show him a page before we start shooting, and he’ll memorize it. His mechanism for doing that is to stop questioning these things,” Eisenberg said. “Kieran is exciting and confusing at the same time.”
Eventually, Chayton and the kids came for two weeks initially, and then Culkin was alone for the next three weeks. “I was in a constant state of panic,” he said. “I just went to this horrible place.” For obvious reasons, the work itself was dark, but Culkin felt an even more depressing feeling that he still can’t describe. “I was absolutely shattered,” he said. “Jesse said, ‘What happened to you?’…” Culkin shook his head. Many actors miss their children. For them, the experience was destabilizing. They dropped them off at the airport, got in their car and shot the scene in Majdanek the next morning.
Still, Peele remembers, Culkin had a hard time getting his work taken seriously with his apparent distaste for conventional engagements. “It’s frustrating,” he said. “Like, you get all these opportunities. You’re missing them. He didn’t respond to emails. He wasn’t available to his agents very often,” Peele said.
Both he and Peele later starred in Scott Pilgrim vs. the World, which also starred Michael Cera and Brie Larson. At age 26, Culkin began thinking about expanding his acting career beyond the family business. But just before shooting began on the film, Culkin’s sister Dakota was killed in a car accident in Los Angeles, and he couldn’t bring himself to go to the shoot. He wanted to make this movie. He wanted to be sad. He missed all the deadlines.
A month later, he sent Peele a text message: Has production begun? She told him this was not the case and that she was attending a cast dinner with film director Edgar Wright. Wright walked out and talked to Culkin for 10 minutes. The next morning Culkin boarded a plane and arrived at his destination.
Looking back, he wonders if it was the best decision. The movie was one of his favorites and the role was tailor-made for him. But he has no intention of “getting over” his misery. In “Real Pain,” Benji makes a choice — not just to feel miserable, but to let it take over him. Would that be healthier? “I’ve never met a man who was miserable and still thinking about prosperity and solving problems,” Culkin said. He got through that period of intense grief. But “I don’t know what to do with it,” he said. “I’m still working on that.”
He met Chaiton at a bar in 2011. He stood next to her and left after talking for a while. Culkin sat down in the empty seat and asked, “Is that your boyfriend?” When Chaiton told him no, he introduced himself. “I’ve never been that forward,” he said. “I’ve never been that close to a woman before that moment.” The two ran into each other during a road trip in 2013. Peele believes that if Culkin has looked more comfortable over the past decade, Charlton deserves credit. She sheltered him.
Cera and Culkin reunited in 2014 when they both starred in Kenneth Lonergan’s play This Is Our Youth. In between gigs, they gambled constantly, trading the same money back and forth for weeks. Cera believed the theater offered something special to his friend — “exciting,” but also a little nerve-wracking, as Cera describes acting with Culkin. In front of an audience, he was a performer — “energetic, spontaneous, creative, free,” Cera said.
According to Succession lore, Culkin was first asked to audition for the role of Greg’s cousin by the cast, and later by Nicholas Braun. But after reading the pilot, Culkin was drawn to Roman and on a whim submitted a tape for the role. Jesse Armstrong was instantly convinced: upon seeing Culkin, he couldn’t remember who Roman was before him.
Culkin was grateful he didn’t face the same confusion. He’s very aware of the difference between himself and the character. “Roman—he’s a pretentious guy,” he said. He doesn’t even read comments and “isn’t on the Internet,” so it was my duty to point out to him that there were rumors on social media last summer that Taylor Swift’s song “When Emma Falls in Love” was about his relationship with Stone’s Chronicle. (He didn’t hear it. He was relieved to hear that Swifties didn’t hate him.)
Still, the end of Succession made an impact on him. When he finished his final scene with Sarah Snook, who plays Roman’s sister Sif, “I hugged her and cried,” he said. In April, he went to London to see Snook’s performance in The Picture of Dorian Gray, which he called “fantastic.” “A Long Day’s Journey Into Night.” Later, he saw Jeremy Strong in New York in “Enemy of the People.” When I told him I felt sorry for Strong, who has a bucket of ice thrown on him every time he performs, he laughed. “I think he liked it,” he said. “It’s somebody’s bread and butter.”
Culkin rarely experiences anxiety between projects, and he enjoys coming home for dinner – a daily opportunity to introduce his children to foods that interest them. “He cooks more than I ever do,” said Chatten. “He goes out of his way to prepare these meals I know they won’t touch.” Lately the guys have given up on elaborate roast chicken in favor of French fries. He said he’s been sent about 50 lousy movies and TV shows in the past six months. None could tempt him.
Theater seemed to offer better opportunities; next spring he would star in “Glengarry Glen Ross” with Bob Odenkirk and Bill Burr. After the production was announced, he told me that when he read the script, he had never seen the play performed but “immediately fell in love with the language” and was thrilled to have the opportunity to reinvent his iconic character, Richard De Roma, in color. (It helped that the producers agreed to change his schedule to be with his kids on Sundays.)
As dinner was coming to a close, I asked Culkin if there were any genres he was interested in or directors he would still like to work with. He smiled. He and Matthew Macfadyen, who played Tom Wambsgans in Succession, often joked about actors speaking poetically about their future roles. “We’d say, ‘I want to be a cowboy’ … ” Culkin said, imitating a little finger gun. “Or say, ‘I want to play a character with a mustache.’
In fact, he just wants to find good parts in a good project. Since taking the throne, he has tried not to seem precious, but he has proven bad at lowering his standards. If he was going to dedicate himself to hard work, it had better be worth it. That’s why he is so choosy. He had a backup plan ready.
“I kept thinking I was going to buy a lottery ticket,” he said. But that’s no problem, right? He’s already won.
In this story: Beauty by Amy Komorowski. Produced by Boom Productions.
