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How Kieran Culkin Survived Childhood and Made Peace with the Family Profession

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Kieran Culkin, photographed at the Down Town Association, in New York City. Vest and pants by Brioni; shirt by Prada; shoes by Brunello Cucinelli.

Photograph by Peter Yang. Styled by Tony Irvine.

“All happy families are alike; each unhappy family is unhappy in its own way.” But who are the happy families of actors? Certainly not the Barrymores, though Drew survives, even flourishes, after the fire starter of her childhood. Perhaps not the Baldwins, Fondas, or Carradines, and definitely not the fictional Tyrones of Eugene O’Neill’s Long Day’s Journey into Night. The Culkins, however, now well into their 20s and 30s, are another story, perhaps most reminiscent not of a dynastic Hollywood brood but of a fictional literary one: J. D. Salinger’s Glass family.

Seven children, raised as performers, are each uniquely talented and yet reluctant to be famous, brutally aware of the trappings of celebrity and determined to find a peaceful path forward. Like the Glass children, the original Culkin seven—Christian, Dakota, Macaulay, Kieran, Rory, Shane, and Quinn—constitute a group of highly individualistic, sensitive, and creative people who have gone into and out of the public eye. And, more recently, out from under the shadow cast by the family’s most famous offspring: Macaulay Culkin, the hugely popular star of Home Alone (and the first child actor to be paid $1 million, for his role in My Girl, as well as the second-youngest celebrity to host Saturday Night Live, at age 11—Drew Barrymore hosted at age 7). For now, all attention is turning to 36-year-old Kieran—two years younger than Macaulay (called “Mac” by his siblings)—stemming from his galvanizing performances in Igby Goes Down, onstage in This Is Our Youth, and now as Roman Roy in Succession, this year’s surprising summer hit, on HBO. Right behind him is Rory, his immensely talented brother, now 29.

If family dynasties are not rare in Hollywood, what is rare is the metamorphosis of a child star into a successful adult actor. But it does happen. Kieran and Rory have grown up on film like Drew Barrymore and Elizabeth Taylor (who once said she could not remember a time in her life when she wasn’t famous). America’s sweetheart, Shirley Temple, didn’t quite make it as a grown-up star (but she did become ambassador to Ghana and to Czechoslovakia). Macaulay is no longer a child, nor is he any longer an actor (with a few exceptions here and there), but his experiences as both have proven to be essential elements in the alchemy that is the Culkin mystique. And his siblings have been paying attention.

“I’ve seen him play the bully and the bullied, because I think he’s capable of being both,” says Quinn of her brother Kieran. Jacket by Paul Smith; shirt by Brioni; pants by Raf Simons; boots by Dries Van Noten.

Photograph by Peter Yang. Styled by Tony Irvine.

The Family Business

It’s late summer. We see Kieran standing alone, looking a little lost, with his dark hair falling over his eyes, scanning the lobby of the Bowery Hotel, in New York City, for someone he’s never met. He has an unassuming manner—a kind of shy bewilderment that anyone would want to be waiting for him. We meet politely, like spies. He settles into one of the worn, Moorish-looking pieces of furniture in the Bowery’s lobby, its hunting-lodge darkness belying the scorching August sun outside. He orders an old-fashioned with Laphroaig, a scotch that’s “very smoky. It’s like drinking a tree,” he says.

He discovered the whisky while in England, where the final episode of Succession was filmed. “Right after I finished the season, I went out with Jeremy and Nick,” he recalls. (Jeremy Strong plays Kendall in the series, the second son of Logan Roy, who attempts a hostile takeover of his father’s empire. Nick is Nicholas Braun, who plays Logan Roy’s gangly great-nephew, who seems to be a sheep among wolves.) Jeremy introduced him to the drink. He’s “the guy who knows all the hit restaurants and bars—whatever the rich people are doing, that’s him getting into character.”

As a gesture of goodwill, I hand Kieran a gift, a slender book about the soundtrack to the Super Mario Bros. video game. He’s delighted. With Nintendo, “the music was insanely important,” Kieran explains. “Castlevania! Just hearing the first couple of notes of that game cheers me up if I’m having a bad day.” If they weren’t sublimely gifted actors, the Culkin kids might have been world-class gamers.

Asked about how he got into the family business, Kieran answers, “Oh, I’ve been doing this for about 29 years.” Their family patriarch, Kit Culkin, had been an actor from a young age and seemed determined to have his progeny follow in his footsteps. “My parents’ friends were running a little theater, the Light Opera of Manhattan, and whenever a production needed a kid, they were like, ‘What age and what gender? We’ve got seven of them right over here,’” Kieran explains. Kieran felt that they were often used just as onstage props. His late older sister, Dakota, who died in a car accident in 2008, was not at all interested in acting, but was pushed into it until she put her foot down. All seven of the Culkin children have been in—or are in—the business. (Shane was in the celebrated 1988 production of Our Town, with the late monologuist Spalding Gray.)

Given his early start, it’s surprising to hear Kieran say that he doesn’t have “any technical training whatsoever. I was just sort of already doing it, continued to do it, and then, Oh, shit, I have a career!” While he was ultimately cast as the feckless, outrageous Roman Roy (a borderline personality by his own admission at the end of Season One of Succession), he had been originally considered for the character of 26-year-old Greg Hirsch (a.k.a. “Greg the Egg”). But Kieran felt that he was too old to play that character, and fell in love with Roman the moment he appears in the script and says, “Hey, hey, motherfucker.”

Quinn, 33, is also an actor (she played Macaulay’s sister in The Good Son in 1993). She recently told Vanity Fair, “I’ve actually had people tell me when they watch, ‘Oh, he’s not really acting. He’s just being himself.’ I’m like, ‘You don’t know him. He’s not like that,’” although she admits that, growing up, “he was always kind of known for challenging anybody in a position of authority. The character isn’t him, but it’s very similar to him. My brother definitely has more heart than that. I’ve seen him play the bully and the bullied, because I think he’s capable of being both.”

Kieran felt that he didn’t need to do any research for the part. He immediately understood the Roy family dynamic: that they’re so rich and powerful they don’t have to suffer consequences. “You can be a total idiot, a fuckup—doesn’t matter. Keep dropping out—doesn’t matter. You can say whatever you want, do whatever you want—doesn’t matter. Roman can slap his sister in the face, and that’s O.K. ‘What are you going to do? Sue me?’”

Home, Not So Alone

For the first nine years of Kieran’s life, the Culkins lived in a railroad apartment in a tenement on East 94th Street and Second Avenue, “barely suitable for a couple,” Kieran says. “It was just a hallway, and there were no separating doors, except for the bathroom, which didn’t have a lock. They raised seven kids in that apartment—for years! They just kept bringing babies home to this little space.” Not surprisingly, it was a rough-and-tumble atmosphere. “Some of us would go to school,” recalls Kieran. “Some would not. We used to watch wrestling. I remember watching Macho Man versus Brutus ‘the Barber’ Beefcake, and then me, Shane, and Mac would imitate those matches.”

“We’re quite peerless because of our experiences,” says Macaulay.

Their mother, Patricia Brentrup, held it all together. The family’s longtime agent and manager, Emily Gerson Saines, described her as someone who “has maintained strong family values, like the family having a meal together, the Christmas tree, Thanksgiving. These are all important things to Patty, and she instilled that in her kids.” According to Kieran, he still has “a great relationship” with his mother, who, after 30 years of living in New York, married a different man and moved to Billings, Montana. “She’s taught me a lot. She’s a wonderful woman.”

But life with their father, Christopher Cornelius “Kit” Culkin, was not so wonderful. Kieran and Mac have no contact with him. Kit was born and raised in Manhattan—the son of a public-relations man and a mother who became his manager—along with his brother and sister (his sister being the actress Bonnie Bedelia, perhaps best remembered for playing drag-racer Shirley Muldowney in Jonathan Kaplan’s 1983 film Heart Like a Wheel). As a young actor, Kit had an auspicious beginning, appearing in 1960 with Laurence Olivier in Jean Anouilh’s Becket, and four years later on Broadway in John Gielgud’s production of Hamlet, starring Richard Burton.

Though his career foundered and he worked for a while as a church sacristan, Kit found his way back into show business through Macaulay. Soon he was managing the biggest child star since Shirley Temple. Macaulay’s blockbuster film, Home Alone, became, at the time, the third-highest moneymaker in the history of the movies (after E.T. the Extraterrestrial and the Star Wars films). Its huge success even gave rise to a Hollywood phrase, to be “Home Aloned,” which meant having your own movie’s box office dwarfed by another wildly popular film.

Its sequel, Home Alone 2: Lost in New York, earned more than $359 million. Its success gave Kit tremendous influence in Hollywood because, if you wanted Macaulay, you had to go through Kit. In 1993, Premiere magazine rated Kit Culkin the 48th most powerful person in Hollywood, ahead of Michael Douglas and Eddie Murphy, but he quickly began making enemies. Studio executives grumbled that Culkin Sr.~tried to use his power to wrest creative control of Macaulay’s movies.

At home, according to a revealing interview with Macaulay on Marc Maron’s WTF podcast, Kit was allegedly a domestic tyrant, terrorizing his children with punishing threats and humiliation. Ultimately, he alienated his children and his wife and eventually lost everything. It even affected Macaulay’s popularity; New York magazine noted that his “rapid ascent seemed less adorable and precocious the more people learned about his home life.”

Macaulay told Marc Maron that he felt his father was “jealous” of him, because “everything he tried to do in his life I excelled at before I was 10 years old.” Whenever he and his father left to make a movie, Macaulay found himself “locked in a [hotel] room with a man who didn’t like me,” but at least it spared the rest of his family months of their father’s cruelty. (Kit Culkin could not be reached for comment.)

Macaulay described how he walked away from acting after playing the Harvey Comics character in the 1994 movie Richie Rich. He told his parents, “I’m done, guys—hope you all made your money because there is no more coming from me.” Patricia (who was not married to Kit) filed for custody, igniting a bitter public battle culminating in Macaulay taking his parents to court to block them from controlling his $17 million in earnings. “I learned how to read court papers at 14,” Macaulay told New York in 2006, and from then on he and his father were estranged.

It was an estrangement that went deep.

Rory, Macaulay, and Kieran Culkin, photographed by Julian Broad for V.F.’s April 2001 issue.

Photograph by Julian Broad.

Kieran, too, had difficulties with his father. “He’s not a good dude, but he wasn’t really a big part of my life after the age of 15. Sometime in the 90s, he went away and disappeared for two, three weeks, and the babysitter remarked to my mom, ‘You know what’s funny is their father’s been gone for three weeks, and not one of them has said, Hey, where’s Dad?’ Nobody cared, actually. My mom was the parent, so when he wasn’t there it was nicer and better.”

For Macaulay, closure didn’t come until he wrote about his father in his novel-cum-memoir, Junior, published by Miramax Books in 2006 when he was just 25 years old. Harrowing open letters to his father stand out among pieces of whimsy and a few fond, early memories of Kit. (“I used to love to help him clean the organ [in church] or ring the big bells in the bell tower. And on one of those days when I had the privilege of going to work with him, I asked him if I could go to the moon.”)

“It didn’t have to be like this,” he writes in a letter that begins, “Dear Father.”

“We could have stayed poor. . . . You showed me what it was like to be afraid. . . . You hurt people a lot, you know. I am not just talking about your family and the other important people around you; you hurt our name. I should know. Did you know I had to apologize on your behalf way too many times? . . . You made a lot of people cry. You made my mother cry.”

Macaulay grew up fast, getting married at 17 to the actress Rachel Miner, also from a theatrical family, whom he’d met at the Professional Children’s School, in New York City; but they separated two years later. Then came an eight-year relationship with the actress Mila Kunis (That ‘70s Show, Black Swan), but his outsize fame proved burdensome; it was like having a third person between them. Fans still stalked him in the streets.

Being Famous

Kieran was about eight or nine when Macaulay’s immense popularity hit the family like a tsunami. “There were times when he was just a kid walking down the street and people would start surrounding him.” Once, a cabdriver recognized Macaulay when he was heading home with his brothers. “He was being kind of creepy,” Kieran recalls. Shane had the cabdriver drop them off at the corner, but when they started walking toward home, the taxi crept along behind them. On another occasion, when Macaulay pulled a cap low over his forehead in an attempt to look anonymous, a woman walked up, grabbed the cap off his head, peered at him, and said, “Yeah, it’s him.” And then: “You’re not that cute.”

It makes sense that Kieran sees fame as “not a nice thing. I think well-adjusted, smart people that experience it first- or secondhand would not pursue it,” he says. “I’ll totally take personal happiness over success, absolutely. If I’m miserable, then what’s the fucking point?”

Macaulay realized early on how much his fame isolated him. “We’re quite peerless because of our experiences,” he admitted. “We can’t really look around and find someone who’s had a similar upbringing. It’s added to our closeness.” That was a big part of his friendship with Michael Jackson. “He understood, because he grew up in a similar way,” says Macaulay. “He saw certain aspects of himself in me and our family, and he wanted a safe time and a safe place to be himself.” Both Macaulay and Kieran visited Neverland Ranch, but it was Macaulay who had to go to Neverland to feel like a normal boy.

Igby Goes Down

Burr Steers’s 2002 dark comedy, Igby Goes Down, became a cult classic that made other actors and directors take note of Kieran Culkin—but he almost didn’t get the part. He auditioned three times for the lead role of a disaffected prep-school dropout struggling to find himself (not unlike that other famous Salinger character, Holden Caulfield). Steers, the writer-director, initially passed on the audition tapes Kieran had sent in, but he had trouble casting the lead role, so he went back to Kieran. They met at a diner where, again, Steers told him he didn’t think he was right for the part. But he changed his mind when Kieran, then 18, looked at the frazzled director and said, “You look like shit.”

“I wasn’t trying to be an asshole. I just didn’t have much of a filter then. He said he had such an urge to hit me upside my head,” but that’s when he knew Kieran was right for the part. “How many people fucking hit Igby in that movie? He gets hit by five or six characters!”

It was Steers’s first movie, “and I had everything riding on it,” he told V.F. in a recent phone call, “but it had taken me almost five years to get it made.” He found that, with Kieran, “you’re not aware of how incredibly emotionally deep he is. Technically he’s so strong because he grew up in front of a camera, and then you add to that what he brings emotionally.” Nonetheless, Steers admits to having been “a complete asshole to him” on the set. “I would clamp down on canned line readings. Kids get in those rhythms from those TV shows and the face acting where they’re commenting on every line by making a face.” Sometimes in the middle of a take Steers would say, “Kieran, that was Nickelodeon. Go back.”

Starring with veteran actors Susan Sarandon, Jeff Goldblum, and Bill Pullman, Kieran felt that “all of the acting classes I could have taken were in those five weeks it took to shoot Igby.” Kieran feels that his grown-up acting career started with Igby, and “all of that was all Burr Steers. I feel I owe him my career.”

Susan Sarandon played Mimi Slocumb, the icy mother dying of breast cancer, who has her young sons euthanize her in a scene that is both comic and harrowing. It was a challenging role for Kieran. “I love him,” she told V.F. “He’s very talented; he had a huge responsibility in Igby, with a first-time director, but he rose to the occasion and gave a great, very difficult performance. He’s also one of the sweetest young men I’ve met.”

The MacCulkins

Emily Gerson Saines has represented the Culkins for 24 years, much of their lives. “Kit had let go of their previous agent, and they were taking meetings at the William Morris Agency, and I was at one of those meetings,” Saines told V.F. “At that time, Macaulay was quite famous; it was probably 1995. Kit said, ‘If you represent Macaulay, you represent the whole family.’ I was like, O.K., I’m down with that, and I signed them.” But, after signing, Macaulay immediately made it clear that he no longer wanted to act. “He just wanted to be a kid, to have friends and hide from the spotlight.” So Saines turned her attention to Kieran, then 12, and Rory, 6, but there came a period “when Kieran was not particularly into it either. Neither Macaulay nor Kieran chose to act. It was, to a large degree, chosen for them. For Rory, on the other hand, it was always his choice.”

Saines saw that “there was the added complication” that Kieran was touted as Macaulay Culkin’s brother. “I don’t care whose brother he is. There’s this public perception of them that they’re one person—or Macaulay’s brothers.” Their sister Quinn perhaps put it best when she told V.F., “I’ve even been called ‘MacCulkin,’ like I’m a collection of Culkins. As much as we may look alike, we’re all very different. Mac has his way that he carries himself, and Kieran, and Rory. You see it even in the way they stand. It’s very telling of who they are individually.” Perhaps that best explains the brothers’ reluctance to be photographed together for this story, preferring to be seen as persons in their own right—unique, even if uniquely Culkin.

“I’ll take happiness over success,” says Kieran. “If I’m miserable, what’s the fucking point?”

With Igby Goes Down, all of a sudden attention focused on Kieran, especially after his nomination for a Golden Globe and winning a Critics Choice Award. “But he really had an aversion to all the press attention,” recalls Saines. “He used to say to me, ‘Can’t I do this and not be a celebrity?’ But it’s hard to not be a star when you’re being nominated for awards and your movies are critically acclaimed.”

This Is Our Youth

Kieran called Saines in 2016 after a two-year hiatus to say, “You know, I think I want to act again. I want to do This Is Our Youth.” Written by Kenneth Lonergan, who would win a best-original-screenwriting Oscar in 2016 for Manchester by the Sea, the play has become a perennial showcase for young actors (such as Matt Damon, Jake Gyllenhaal, Casey Affleck, Anna Paquin, Summer Phoenix, and Mark Ruffalo). It’s a three-character play about young, privileged New Yorkers desperately trying to grow up: a forlorn Warren Straub, who has stolen $15,000 from his abusive father; the more confident and worldly Dennis Ziegler, who spends the ill-gotten gains on cocaine; and Jessica Goldman, a high-strung fashion student whom Warren tries to woo.

“I did that show back in 2002 in London’s West End playing Warren,” Kieran recalls. A decade later, Kieran was instrumental in reviving the play in Australia, followed by a successful run in 2014 at New York’s Cort Theater, where he played Dennis opposite Michael Cera and Tavi Gevinson. For Kieran, This Is Our Youth was his “dream job.” He loved the play; he loved the language; and he loved all the roles—”part of me wanted to play fucking Jessica. I felt that was such a great part.”

Caption: Clockwise from right, Kieran, mother Patricia Brentrup, father Kit Culkin, and Macaulay, 1990. Rory and Kieran, 2000. Amanda Peet and Kieran in 2002’s Igby Goes Down. Kieran and Sarah Snook in 2018’s Succession.

Clockwise from right, by Steve Wood/Shutterstock, by Richard Corkery/NY Daily News Archive/Getty Images, by Myles Aronowitz/© 2002 United Artists, by Ursula Coyote/HBO.

Jessica was played by Gevinson, the precocious writer and fashion blogger turned editor and actress. “I loved working with Kieran,” she told V.F. “Between him and Michael [Cera], I laughed more in those eight months than I have in my whole life. I had a chip on my shoulder going in, because I’m not trained, and it was my first professional theater production, and there’s much ado about Broadway. I don’t know how an actor’s supposed to prepare. It helped me to be around Kieran, who’s basically a mechanic: ‘This is a task. This is my job. This is the only thing I know how to do, because I have no other skills, and I didn’t go to college . . . ‘“

They socialized a lot, going to the Culkins’ Christmas and New Year’s Eve parties, and in Chicago they had “a Nintendo 64 in the dressing room, and then we upgraded to a Wii once we moved to Broadway,” said Gevinson. She sometimes played a kind of three-dimensional charades with Kieran and his wife, Jazz, “where you would combine clues. You’d somehow find a way to act out ‘Woody Allen Ginsberg,’ and sometimes it would be five clues long.”

Lonergan, a big fan of Succession—and not just because his wife, J. Smith-Cameron, plays the family consigliere, Gerri Killman—understands Kieran’s not wanting to deal with the level of public adoration that Macaulay endured. He saw how Macaulay was “widely attacked, because like all child stars, everyone raved about him, and then two years later he became the poster boy for what’s wrong with child stars. They did the exact same thing to Haley Joel Osment—the kid who was in The Sixth Sense. It’s two years of ‘What a genius,’ and then five years later they’re like, ‘At least they didn’t cast Haley Joel Osment.’ Or ‘Thank God it wasn’t Macaulay Culkin.’ All the actors did was take more jobs, and then they did something terrible—they grew up.”

Rory

Lonergan’s arc as a successful playwright and screenwriter has been entwined with two of the Culkin brothers. Lonergan first met Rory, then nine, at an audition for You Can Count on Me, in 1999. “We saw a bunch of little boys” for the role of Rudy, the son of Laura Linney’s character, who is raising him alone in a small town until her unreliable brother, played by Mark Ruffalo, shows up. “Rory came in,” Lonergan recalls, “and he was actually carsick from the ride to the audition, and he was very quiet, very real, and just immediately engaging. He was right on the money for the part. I don’t know why, because he barely said anything.”

That same year, Rory memorably played the younger brother of Joaquin Phoenix’s character in M. Night Shyamalan’s Signs, and two years after starring in You Can Count on Me, Rory appeared briefly in Steers’s Igby Goes Down, playing Kieran’s character Igby’s younger self. (He also played a younger version of Macaulay’s character in Richie Rich.) Though he’s nearly silent in his scenes in Igby, Rory’s portrayal is heartbreaking, especially when he watches his father (played by Bill Pullman) have a spectacular breakdown in the shower. It’s a key to Igby’s grown-up disaffection, and Rory conveys that flawlessly.

Rory loves acting—Kieran thinks he’s an extremely talented actor—but he’s wary of being turned into a product, a “MacCulkin.” However, he is in danger of becoming a movie star when his next film, Lords of Chaos, is released early next year. Based on the book Lords of Chaos: The Bloody Rise of the Satanic Metal Underground, by Michael Moynihan and Didrik Søderlind, it’s an account of the Norwegian black-metal scene in 1993. “I’m really proud of it,” he told V.F. “It’s rare when I get behind something and feel prideful of it and want to show it to people, and this is one of those. It’s sort of my baby right now.”

Macaulay

“I’ve been me my whole life,” Macaulay told V.F., shortly after returning from a trip to Germany. “I knew my life was unique, but it wasn’t until I got older that I really understood exactly how unique it was. We were just another family on the block, and then, all of a sudden, there was a sea change in the way that even the neighborhood kids would treat us. So we were always really protective of each other.”

Does Macaulay miss acting? Not really. “When I was doing My Girl,” he recalls, “they released a couple of hundred bees onto me, actual live bees. I knew that this was not something that every kid was doing. At the same time, it was just another day at the office. I’m pursuing other kinds of things—I’m painting and I’m doing a comedy Web site. I’m writing. I’ve been described by a good friend of mine as ‘a man of leisure.’ I’m essentially a thirtysomething retired person. For me, I feel a certain level of comfort and peace.”

His passions reflect an antic sense of humor, including his band, the Pizza Underground, a parody of the Velvet Underground that reworks Velvet’s songs to make them about pizza (one of his favorite foods). “We recorded [the songs] on my dining-room table, and then forgot about it.” One of the band members put them on Bandcamp, and “the next thing you know, I’m touring in an underground pizza cover band for a year and a half.”

Then there’s his comedy podcast and blog, Bunny Ears, which he created with his friend Matt Cohen. Launched while Macaulay was living in Paris, it’s a satiric, Dada-like response to lifestyle blogs like Goop, reflecting his sense of absurdity and fun, “from the mind of a world-famous celebrity turned world-famous recluse.” Some of the posts: “How to break the mindset that you can do anything you set your mind to”; “How to win the social media ‘most wounded person award’”; “Décor so minimal you’ll wonder if you even exist”; “Sorry, haters: I can call my dog ‘My Baby’ because I gave birth to him”; and “Exclusive: Macaulay Culkin interviews the swarm of bees from My Girl.”

The Culkins vs. the World

The director Edgar Wright (Baby Driver) was impressed by Kieran’s “amazing comic timing” when he read for the supporting role of Wallace Wells, a gay character in Wright’s film Scott Pilgrim vs. the World. But just after he was offered the role, something terrible happened. On December 9, 2008, Kieran’s older sister, Dakota, then 29, was fatally struck by a car outside Brennan’s, an Irish bar on Lincoln Boulevard in Marina del Rey, California.

“We didn’t want to bother him,” recalls Wright. “When someone is in such terrible grief, you can’t leave voice mails. We left him alone for a long time.” Kieran passed on the role, and Wright had to look for a replacement. But one night at a cast dinner in Toronto, the director overheard actress Alison Pill mention that she had just spoken to Kieran, who regretted giving up the role. Wright says he ran out of the restaurant and called Kieran, who told him, “ ‘Yeah, I wanna do it, but I have to tell you something. I’ve dyed my hair green and I’ve put on quite a lot of weight ‘cause I’ve been drinking a lot.’ He came up and worked out with the cast every morning, and he was an absolute pleasure,” Wright says. “The audience loved that character.”

Succession

Toward the end of Season One of Succession, embattled media titan Logan Roy (played by the veteran Scottish actor Brian Cox) raises his glass to toast his only daughter at her wedding. The family patriarch has actually crashed the event, having been disinvited by his daughter Siobhan “Shiv” Roy (Australian actress Sarah Snook), but he manages to control his Lear-like fury toward his mutinous children, declaring, “Here’s to family, the only thing that counts.”

Succession—like success—has many fathers (and one mother), including creator and show-runner Jesse Armstrong and executive producers Ilene S. Landress, Kevin Messick, Will Ferrell, Adam McKay, and New York columnist Frank Rich. According to Armstrong, Rupert Murdoch and his sprawling media empire initially inspired him to write the series. The familial battle for control in the Sumner Redstone dynasty also influenced him, but, as Rich noticed, once they started shooting the pilot, “suddenly we’re thinking, God, these boys are a little bit like the Trump boys. It wasn’t something that had been planned.”

When it came time to cast Roman Roy, as soon as Kieran read on camera for the part, “that was it,” recalls Armstrong. “That’s Roman. Done. He just had an instant feel for the part. In the pilot, there’s an early scene where they’re discussing changes to a trust, and Roman is lying the wrong way up on a couch. That physical gesture is one of those instinctive things which speaks volumes about his relationship to this family. He had a sense of his character from the beginning.”

Alan Ruck, who had his own youthful success as Cameron Frye in Ferris Bueller’s Day Off, in 1986, plays Connor, the eldest and most removed of the Roy clan. He also cites Kieran’s being “upside down on the chaise longue” as a character revelation. At that moment, Ruck thought, O.K., I know who you are. He describes Roman as “the most sociopathic of all of us—I mean, we’re all terrible. But because Kieran has so much charm, you laugh at the terrible things that come out of his mouth.”

Kieran will reprise his role as Roman Roy in Season Two of the hit HBO drama. Suit by Dunhill; shirt by Prada; boots by Dries Van Noten; watch by Patek Philippe.

Photograph by Peter Yang. Styled by Tony Irvine.

Snook agrees, saying that “one of the reasons Roman can get away with saying or doing just about anything is because of his wit. And Kieran is possessed of a terrific wit in his own right.” Her character has “a unique relationship with all her brothers, but with Roman, they’re truly close. There’s a real family feeling there. Though they fight, they would probably do anything for each other. But, of course, we don’t know what the second season will hold.”

To Brian Cox, who plays patriarch Logan Roy with cunning, cruelty, and charisma, working with Kieran was “an absolute, constant delight. I’ve never known a young actor with such a sense of immediacy. Child actors are often maligned, but the thing about them is they just do the job. I’ve always found that there’s an exceptional professionalism about them, because they learn at an early age—it kind of comes with their mother’s milk. There’s no angst. It’s unusual in American actors to have that sense of lightness. British actors have it a lot, but to find it in somebody like Kieran is very, very unusual.”

Cox’s favorite scene unfolds near the end of the season when the bickering between Roman and Shiv erupts into a fistfight that has them rolling on the floor, punching and pulling hair like 10-year-olds. Sarah Snook told V.F. that, although “the fight scene was blocked so we’d be safe,” they really got into it. “I think I even lost a hank of hair! I forgot that Kieran, because he’s such a fan of World Wrestling—he knew all these moves.”

Brian Cox would like to see Kieran do more stage work: “There are lots of things that I’d love to see him in. For example, I’d love to see him play the young Mozart in Amadeus. I think he’d be extraordinary . . . As long as I could play Salieri!”

The Culkin-Family Romance

Like many deposed tyrants, Kit Culkin lives in a kind of exile, according to a Daily Mail article from 2016. Now 74, he was laid low by a debilitating stroke four years ago that left him having to relearn how to speak. He lives alone in a small house in Grant’s Pass, Oregon. His longtime companion, Jeanette Krylowski, died last year. He’s been sighted on rare occasions, sporting a long, gray patriarch’s beard and a trilby hat. The Daily Mail reporter asked if he hears from his most famous son. Kit replied, “I don’t consider him a son anymore.”

But the rest of the Culkins are thriving. “You know what’s really been lovely to see is the brothers,” says Emily Gerson Saines. “I think no one can understand the lives they’ve led but them. They have common experiences that are impossible to explain to people. I think none of them think or behave like actors.”

For one thing, they share a passion for professional wrestling and follow WrestleMania around the country. “We all just recently went to Rory’s wedding,” Saines recalls, “and it was so incredible, because Kieran was there with his wife, and Macaulay was there with his girlfriend, and the women all get along really well. It just melts my heart to see them all together like that.” Rory’s marriage to the cinematographer Sarah Scrivener was officiated by Paul Heyman, the booming-voiced WWE announcer, “and the reason his wedding was in New Orleans was that’s where WrestleMania was at that moment. Everybody’s doing what they want to be doing, and they’re doing really great work. And they’re all happy in their personal lives. That’s as good as it gets in this world.”

Grooming by Desirae Cherman; For details, go to VF.com/credits.

CORRECTION: An earlier version of this story misspelled the surname of Kieran Culkin’s mother. It is Brentrup.

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