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Martinis and Red Meat With Kieran Culkin: The ‘Succession’ Star on Childhood, Co-Stars and Fame

The hyperactive breakout of HBO’s dynastic hit show gets candid about growing up Culkin, the behind-the-scenes dynamics of his onscreen family and his early fears of Hollywood success: "I knew I would not have been able to handle it. So I quite literally ran away from it."

“My mom would do it this fast all the time,” says Kieran Culkin, sprinting through exhibits at New York’s American Museum of Natural History — a Cro-Magnon family, some bighorn sheep, was that a giant millipede? — as I scramble to keep up. “She would come in here with seven kids, throw a quarter into the admissions, and we’d just run through. We’d climb shit. Security would yell at us.”

They still are yelling at him. Today, a guard recognizes Culkin and shouts in a thick New York accent, “Roman’s da man!” a reference to his character Roman Roy — the scene-stealing scion he plays on HBO’s Succession, the Learian family drama poised to return for its third season Oct. 17 following a year-plus COVID-19 delay.

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We were supposed to grab deli sandwiches and sit on a park bench. But it is raining, and Culkin suggested a last-minute change of venue. His shoes are soaked, though not from the drizzles. “I ran through a water fountain last night with my daughter — and they’re the only shoes I have,” he offers, adding that his ensemble of orange sweat shorts, a rumpled short-sleeve shirt and a week’s worth of facial hair is not quite complete, “because there’s no stroller and sippy cup and the diaper bag and all the stuff. That’s my life.”

He and his London-born wife, Jazz Charton, had their second child, a son, in August. Charton, 33, is neither a “former model” nor a “Foley artist,” as she’s been described on the internet, but rather was working in the music department of an ad agency when she met her future husband at a New York watering hole in 2012. “I said, ‘I’m Kieran. You have an English accent. What’s your name?’” he recounts. “She said, ‘Jazz.’ I said, ‘J-A-Z-Z, like the music?’ And she said, ‘Yeah.’ And I said, ‘Well, that’s fucking stupid.’”

That made her laugh and the two have been blissfully in love ever since. They married in 2013. Until now, the couple and their firstborn have lived together in the same one-bedroom apartment in the East Village that Culkin has occupied for two decades. They’re currently relocating to a much more spacious spread in Brooklyn — for Culkin, the equivalent of “moving out of the country because it’s not Manhattan.”

We round a corner and are suddenly awash in the calm, blue light of the Hall of Ocean Life. We sit cross-legged on the floor beneath the museum’s giant blue whale, like a couple of overgrown kids on a school outing. Adding to the surrealness are the dozens of actual kids on actual school outings cavorting around us. And above us — all 94 feet and 21,000 pounds of it — floats the life-size replica of a creature that washed up dead on the southernmost tip of South America in 1925.

“It’s got a Band-Aid on it. Isn’t that clever?” says Culkin, 38, landing somewhere between sincere and sarcastic — his sweet spot. (He also says “Fuck you!” a lot, the way one might say “That’s great!” or “No kidding!”) I glance upward: Sure enough, there is a 6-foot promotional bandage affixed to the right fin — a reminder of the hall’s recent reconfiguration into a COVID-19 vaccination hub. And of what a long, strange year it’s been.

I barely have time to absorb all this when Culkin, energetic and restless, guides us over to a dimly lit diorama of yet another, smaller whale, this one being attacked by a giant squid that was the namesake of 2005’s The Squid and the Whale, Noah Baumbach’s semiautobiographical drama about his parents’ divorce.

“My mom tells the same story every single time we’re here,” Culkin says. “She goes: ‘We used to take whoever the youngest kid was in the stroller and put them right up in front of the squid and the whale. And then every one of us would run and hide. I’d watch you struggling in that stroller, terrified, trying to get out, and we’d all be laughing.’ Like, ‘Yeah, good. Just a pinch of trauma.’ “

In the Baumbach film, the son, played by Jesse Eisenberg, tells a therapist that his fondest childhood memories were of being taken by his mother, played by Laura Linney, to see the squid and the whale. Even though the sharp teeth and tentacles terrified him, the shared experience brought them closer together, and eventually he comes to realize that his father, played by Jeff Daniels, was never actually there for him.

Culkin doesn’t bring any of this up, but there are undeniable similarities there. His story, too, involves growing up in the 1980s in the wilds of New York City, where he was loved unconditionally by his mother and was neglected by his stage-dad father.

Of course, Kieran also had to navigate the murky depths of Hollywood celebrity and a chaotic showbiz family that included his brother Macaulay, the biggest child star in generations. Maybe that’s why Kieran — despite being generally regarded by his peers as an extraordinarily gifted actor, even a generational talent — has actively resisted the pull of stardom for close to three decades.

“I think he has a healthy suspicion for the seedy sides of show business,” says J. Smith-Cameron, who plays general counsel Gerri Kellman, Roman’s closest ally, on Succession — a strange hybrid of mother figure and psychosexual foil to the deeply damaged Waystar Royco heir.

(In reality, Smith-Cameron and her husband, filmmaker and playwright Kenneth Lonergan, in whose work Culkin has frequently appeared, are two of his closest friends and creative collaborators. “My first day of shooting Succession, I looked on the schedule and I see ‘J. Smith-Cameron,’ ” Culkin says of the happy coincidence. “I went, ‘You got to be fucking kidding me.’ “)

“From the time he was a child,” Smith-Cameron continues, “he could see what fame and attention must be like. I think it’s always been: ‘It doesn’t run me. I run it.’ “

With his breakout turn on the buzzy Succession — whose linear audience of 1.2 million actually understates its cultural clout (it won seven Emmy Awards in 2020, including outstanding drama series) and which has earned Culkin Golden Globe and Emmy nominations — the whole “fame and attention” thing is getting harder and harder for Culkin to avoid. There are signs, however, that he might finally be ready to embrace it. At the very least, he’s ready to embrace acting.

“I’m trying to remember the exact moment it hit me,” he says, gazing up at the enormous blue whale’s grooved underbelly, as one might a starry sky. “I think it was at the end of the first season. I remember coming home and thinking, ‘This is what I want to do with my life. I think I want to be an actor.’ I was, like, 36. I’d already been doing it for 30 years.”

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Succession’s one of the best jobs I’ve ever had. It’s a dream. But if I had to pick, it would without question be being a full-time parent,” says Culkin, who had his second child in August. Jacket and sweater by Boglioli, T-shirt by Kotn. Photographed by Heather Hazzan


Some of Culkin’s earliest memories involve being led by his father’s hand into Central Park and posing for 8-by-10 headshots. The entire family lived in a railroad apartment — basically a long studio — at East 94th Street and Second Avenue. Kieran was the fourth born, sandwiched between the three eldest (Shane, Dakota — fatally struck by a car in 2008 — and Macaulay) and three youngest (Quinn, Christian and Rory). His father, Kit, had another daughter, Jennifer, with a previous girlfriend in 1970; Jennifer died in 2000 from a drug overdose.

A onetime stage actor, Kit took a job as a sacristan at New York’s St. Joseph’s Church on the Upper East Side for the free Catholic school education it afforded the kids. Meanwhile, Culkin’s mother, Patricia, was running herself ragged keeping the five boys and two girls, each spaced by two-year intervals, clothed and fed. She did this while holding down a night job at a telephone answering service for a theatrical casting agency. “She must be out of her mind, but she says she was happy,” Culkin says of his mom, who grew up one of 11 children in North Dakota; she is currently visiting from Montana to help out with The One They Call Tito. (They have yet to land on a name for the baby, so Tito is a placeholder.) Patricia and Kit split up in 1995 (they were never married); she married a decade ago and moved to her husband’s ranch. “He’s nice to me,” Culkin says of his stepfather. “He gave me a horse.”

Studies were never much of a requirement in the Culkin household; the four eldest never finished high school. “I kept thinking, ‘I’m going to show up to class,’ ” Kieran says, “and I just didn’t.” Instead, the focus was always on auditions. It began when a neighbor, a stage manager who worked for Light Opera of Manhattan, heard they needed some kids for a production. “He was like, ‘Well, I know these people. They have six or seven of them and I think the father was an actor. Maybe they would be interested,’ ” Culkin recalls. “That’s how it started. Soon it got to a place of like, ‘Sure, you want kids? What gender? What age? Yeah, we got a bunch. Here, take this one.’ ” Culkin was 6 when he started auditioning with his older siblings. “I just liked it,” he says. “It was fun for me.”

His first role was in Home Alone, playing a cousin to his brother’s character, Kevin McAllister. It was, of course, the movie that would change everything for the Culkins. They’d soon be living in a brownstone on the Upper East Side, and Kit would be alienating half of Hollywood with his outrageous requests on behalf of his superstar son. (“Kit Culkin’s demands resulted in a year’s delay in filming, in script changes and in a revolving door of directors and producers,” The New York Times reported of the behind-the-scenes chaos on 1993’s The Nutcracker, in an article headlined, “It Seems the Father of the Child Star Is the Enfant Terrible.”)

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“He reminds me of Robert Downey Jr. He’s certainly the opposite of someone who takes himself too seriously, which is very endearing. It’s up to the rest of us to take him seriously, which we do,” says co-star (and onscreen sibling rival) Jeremy Strong. Pants, sweater, and shirt by Celine. Photographed by Heather Hazzan

None of that really sunk in for Kieran, who during the filming of Home Alone was just a happy-go-lucky 7-year-old enjoying the ride. By 9, painfully cute with giant hazel eyes that drooped at the edges — a trait inherited from Kit — he was cast as Matty Banks, the young son of Steve Martin and Diane Keaton, in Father of the Bride. The production put him up at the Sheraton Universal for three months. The days were fun, but at night, with only his father to talk to, he got lonely.

Unlike Macaulay, who’s said in interviews and his 2007 memoir, Junior, that Kit was physically and mentally abusive toward him, Kieran says he did not have the same “crazy, negative, awful, traumatic experiences as a child actor.” Macaulay’s experiences were so bad, he retired from acting at 15 and emancipated himself from his parents — removing their names from his trust and appointing an independent executor to oversee his earnings — amid their own bitter split and ensuing custody battle. As Macaulay told Marc Maron’s WTF podcast in 2018: “My father was jealous of me. He was a bad man. He was abusive. Everything he tried to do in life, I excelled at before I was 10 years old.”

Kieran insists Kit was never abusive toward him — neither physically nor emotionally — “but,” he adds, “he wasn’t a good person and, yeah, probably not a good parent.” He refers to things his father did to his mother but declines to get into specifics. He can only remember his father as being a constant, unwelcome presence in the household. “He didn’t really bathe,” he says. “He just reeked. I remember thinking, ‘I guess all dads smell awful.’ ” Once, a complete stranger turned to his father in line and declared, “Sir, I find your odor offensive.” Another time, Kit disappeared for three weeks. Through it all, none of the seven Culkin siblings remarked on his absence. “I never looked at him as Dad,” Kieran says. “He didn’t really belong here, and when he was finally gone for good, it made the most sense.”

Instead, it was their godfather, Steve, who served as the central male figure in their lives, taking them on subway rides and Central Park outings whenever Patricia had her hands full with breastfeeding or lunch-packing.

In 2014, Kieran’s brother Shane informed him that Kit was traveling from Oregon to see him on Broadway in This Is Our Youth, a Lonergan play Kieran had previously performed in London’s West End. His father had recently suffered a major stroke that greatly affected his ability to speak, think and move. Culkin put his father’s name on the guest list and greeted him backstage. It was the first time they’d laid eyes on each other in 17 years. “He carried cards around with him that said, ‘I’m not stupid. I understand you. I just had a stroke,’ ” Kieran recalls. “He was telling me that his girlfriend had dementia and it was pretty bad. And so I said, ‘So, when you guys go places, she doesn’t know where you’re going and you can’t communicate how you’re getting there.’ And he goes, ‘Yeah — we’re quite a pair.’ ” The two have not spoken since. I ask if he was at all moved by his father’s visit. “Fuck him,” Culkin replies. “I don’t care.” (Attempts to reach Kit through his sister, Die Hard actress Bonnie Bedelia, were unsuccessful.)

Whatever success Kieran enjoyed as a child actor was dwarfed by that of Macaulay, who was commanding $8 million paydays for films like Richie Rich and hanging out with Michael Jackson at Neverland Ranch. (Macaulay has consistently denied the pop star engaged in any manner of inappropriate activity with him during those visits.) Much of what Kieran witnessed at his brother’s side disturbed him. “He would get harassed on the street,” he says. “One time, a woman pulled off his hat and looked at him and said, ‘Yeah, it’s him! You’re not that cute.’ And then handed the hat back and walked away.”

(Macaulay, Kieran and Rory, who starred in Lonergan’s 2000 film You Can Count on Me, are used to being mistaken for one another. “When I was doing one of the Father of the Bride movies, this woman ran up to me and said, ‘Are you Macluckly Macluckly?’ And I went, ‘No.’ She goes, ‘Can I get a picture?’ I said, ‘I’m not him.’ And in my mind, I’m thinking, ‘Nobody’s that.’ “)

There are three projects “that have defined my life,” as Culkin puts it. One is Succession; the second is This Is Our Youth; and the third is Igby Goes Down. That last one, a minor coming-of-age classic from 2002, has drawn comparisons to The Catcher in the Rye and The Graduate. Written and directed by Burr Steers, the film — which has grown in admiration since its original release — follows the misadventures of a sarcastic prep school dropout surrounded by obscenely rich, affection-withholding relatives who summer in the Hamptons.

Culkin’s performance as Igby drew Hollywood’s attention and earned him his first Golden Globe nomination at 19. He attended the ceremony with Emily Gerson Saines, the same manager he’s had since he was 12 — that’s 27 years. (“The only reason I have any version of a career today is because of Emily,” he says.) It could and should have led to bigger things. Offers came. But Culkin wasn’t interested. “I was definitely not ready,” he says. “I would not have been able to handle it, and I think I knew that. I would not have been able to handle whatever kind of success or attention came from that. So I quite literally ran away from it.”

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“He’s just operating at the very top of his game,” J. Smith-Cameron says of her Succession co-star Kieran Culkin.
Boglioli jacket and sweater, Kotn T-shirt, Saint Laurent pants, Gordon Rush shoes.
Photographed by Heather Hazzan

Culkin reemerged in 2005 to appear opposite Anna Paquin in the off-Broadway play After Ashley. “I was like, ‘I think I could play that. Also it’s a small house. No one’s going to see it, that feels safe, I can do that.’ ” Occasionally, he’d take on a small film role, like Wallace, the “cool gay roommate” in 2010’s Scott Pilgrim vs. the World.

Then he found his feet with This Is Our Youth, a tale of privilege and youthful nihilism set in 1982 New York. When the play ran in London, he played the milquetoast Warren, who steals $15,000 from his dad, “the most dangerous lingerie manufacturer in the world.” But for the Broadway run, he realized it was Dennis — the fast-talking, verbally abusive yet charismatic drug dealer — whom he responded to most. His performance drew rave reviews, with the Times‘ Ben Brantley calling him “a funny and appropriately irritating alpha narcissist, whose will to rule borders on psychopathic.”

Smith-Cameron, who worked with Culkin in Lonergan’s 2009 off-Broadway play The Starry Messenger and Lonergan’s 2011 film Margaret, says: “He’s one of the most available, alive actors I’ve ever worked with or even seen. He’s so inventive and just … released. He’s just operating at the very top of his game.” Lonergan concurs, adding that Culkin has “a unique combination of snottiness and vulnerability that I’ve never seen in anybody else.”

Admittedly, Lonergan adds, his friend can be “a pain in the ass. … You know when you’re at the beach, and it’s beautiful weather, and then it starts becoming night and all these little flies come out and start biting at you? It’s kind of like that. He likes to get on people’s nerves — but he also makes sure he hasn’t done anything too terrible. I’ve never had a quarrel with him that’s lasted more than 24 hours.”

Culkin’s manager passed along the pilot script to Succession in 2016. As the story goes, the casting director wanted him to read for the bumbling Cousin Greg (which went to Nicholas Braun). Culkin instead put three Roman scenes on tape and sent them in. “He was the first of the kids that we cast,” recalls Succession creator Jesse Armstrong, who knew he’d found his Roman a minute into Culkin’s tape. “I had that feeling of gratitude and relief: You’ve written a part, you have a cadence or a sense of a person, but you’re not completely sure if that person exists in the world or if your rhythms will fit anyone. It’s just extraordinarily comforting to see somebody do it ‘right.’ Or more than right — you’ve got a dancing partner, which means you could sort of dance all over the globe.”

Culkin draws from all of his siblings when conjuring up Roman’s rhythms — but particularly Dakota, aka Cody, the sister whose life was cut short by a car accident while crossing Lincoln Boulevard in Marina del Rey in 2008. She was 30. “Cody was funny, man,” he says. “She was the funniest person in the family for sure and had a really dark sense of humor.” He describes his sister as painfully shy — she had no interest in acting — with a taste for other people’s minor misfortunes. Someone tripping on a sidewalk would send her into peals of laughter. For some reason, one of her phobias was the thought of running into a friend or acquaintance while carrying a pizza box. Kieran always found that hysterical.

There’s a moment in the season-three premiere of Succession where Roman — during a heated argument with his sister, Shiv, played by Sarah Snook — makes a buck-toothed face and goes, “Dur-dur-dur-dur-durrr!” It’s a triumph of regressive sibling dynamics. “That’s hers,” Culkin says. “That’s just Cody’s move. You could never get one up on her because, even if she was wrong — ‘Dur-dur-dur-dur-durrr!’ — then she wins the argument. Cody is pretty Roman-y. It’s as if Roman were portrayed by Darlene from Roseanne. Darlene Connor as Roman Roy.”

Cody’s death devastated the tight-knit family. “That’s the worst thing that’s ever happened, and there’s no sugarcoating that one,” Culkin says. “Each one of us handled it very differently. I think everyone was just torn up inside. What has it been, 13 years now? Holy shit. That’s crazy. Jesus fucking Christ. I accepted at the time that this is going to be forever, and it’s never going to be fine. It’s always going to be devastating. I still weep about it out of nowhere. Something funny she did will pop in the head and make me laugh, and then I’m weeping. Sometimes it’s knowing that she’s not going to meet my kids and they don’t get to have her, and it’s hard to describe what she was like.”


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Left: Culkin says his relationship with Succession co-star Sarah Snook (center) is the “most fun sibling dynamic on the set.” Right: Culkin with brother Macaulay (left), circa 1991. Courtesy of Macall Polay/HBO ; Dave Benett/Getty Images

The following evening, I meet Culkin at Wollensky’s Grill, the informal annex to Smith & Wollensky, the venerable steakhouse at 49th Street and Third Avenue. He’s been dreaming of a Smith & Wollensky steak for two years, “since fucking lockdown,” and the place recently has reopened for indoor dining. It’s crowded, loud and boisterous and very New York, with large groups of men enjoying thick slabs of meat together.

“I’m not Mr. Masculine Energy, so that’s why I’m confused,” says Culkin of the tractor-beam-like pull Wollensky’s has on him. “I like the steak. It’s a good steak. And it’s a fucking good martini.”

Culkin shares a story about Macaulay: “I think about this every time I go to a steakhouse. See, I always get prime rib and rib eye confused — because they both have the word ‘rib.’ And one I love, and the other I don’t love. And Mac goes, ‘Well, it’s simple. Here’s an easy way to remember: ‘I’ — and he points to his eye — ‘love rib eye.’ Then he says, ‘Or you can remember it as, ‘I’ — and he points to his eye again — ‘don’t like rib eye.’ It made me laugh.”

“But that doesn’t help you remember at all,” I note, confused.

“It doesn’t,” he says. “He did that to fuck with me. It’s been 20 years, and I still can’t remember — is it ‘I like rib eye’ or ‘I don’t like rib eye’? That motherfucker got me.”

After a lengthy deliberation, our waiter, a scruffy and agreeable guy named Matt Midnight (“It’s a long story,” he says, but doesn’t tell it) offers a suggestion: “You know what we could do? One of you could do the sirloin, one of you could do the rib eye, and then you guys can share — so you have two different steaks at the same time.”

“I love that idea!” Culkin says.

“I could slice them,” Midnight says.

“Fuck you,” Culkin says. “That’s great.”

Two martinis and a rib eye later (he loved the rib eye), I pry around for some Succession gossip. “Snook and J. are possibly my favorite people I’ve ever worked with in my life,” he says. “I think Snook, in particular, I just feel the most comfortable with doing whatever.”

Culkin always refers to his Australia-born screen sibling as Snook, never Sarah. “I guess because my brother’s wife is Sarah. So she’s Sarah. Plus, it’s fucking Snook. Who else is named Snook? It’s actually pronounced Snook” — rhymes with “kook” — “but I can’t even get my head around that. ‘Snooky Snook.’ She has all kinds of nicknames. Some of her friends call her Sally Snacks.”

Snook is the most beloved person on the set. “Like everyone across the board is just like, ‘She’s a remarkable woman,’ almost-to-a-fault kind to everyone,” Culkin says. She once booked a coffee-and-pastries truck on her own dime, he marvels, to keep the crew caffeinated during an arduous night shoot. She’s also the most fun to improvise with. “I’ll just throw at Snook, and she’ll catch the fucking ball and bounce it back at me and elbow me in the face. It’s just the most fun sibling dynamic on the set. We get to play around and be cruel to each other as our characters. That’s even more fun because between the two of us, there’s nothing but just pure joy and love.”

The working dynamic is a little different with Jeremy Strong, who plays Roman’s older brother Kendall, who at the start of the new season has launched a full-scale mutiny against his father, Logan (Brian Cox), for control of the family media empire. “It’s funny, when I improv with him, when he comes in the room, I often talk about how ugly Kendall is,” Culkin says. “And I went up to him between takes and was sort of, ‘You know I don’t actually think you’re actually ugly, right? That’s me trying to disarm you as Roman.’ “

“There’s a lot of us in our characters,” Strong later confides. “There’s probably a fair amount of Kendall in me, and there’s a fair amount of Roman in Kieran. It’s often said of Roman that you don’t see him coming. In that sense, Kieran, too, has this smoke-screen layer of wit and joviality — but underneath there is an incredibly aware, serious, highly attuned individual and very powerful artist. He reminds me of Robert Downey Jr. He’s certainly the opposite of someone who takes himself too seriously, which is very endearing. It’s up to the rest of us to take him seriously, which we do.”

A recently unveiled Succession character poster features a severe-looking Roman and Gerri; Roman is seated, while Gerri stands behind him in the dominant position, one hand dipping into his unbuttoned shirt. It set the internet on fire. Will they finally succumb to their mutual weirdo lust and ascend to power-couple status in season three? No one is saying — but that it’s even gone this far is delightful to both Culkin and Smith-Cameron.

“I remember saying to my wife in season one, ‘I really hope something happens sort of sexually or romantically between those two, but I don’t know that it ever will,’ ” Culkin remembers. “But we were sure trying. I would flirt with J. in the most obnoxious way, just to fuck around.” During filming of the season-one finale, Shiv’s wedding set at a Scottish castle, both characters spontaneously spun around to check out each other’s butts. “I remember the writers all laughing,” Smith-Cameron recalls, “but it never occurred to me that it would inform anything they wrote.”

By season two, Roman and Gerri’s naughty pas de deux had become canon. For Roman — whose sexual development took a wrong turn somewhere around the dog cage he supposedly was kept in as a child — Culkin theorizes it’s all in the wrongness. “Because it’s so not supposed to happen. It’s like, ‘Could you imagine what Dad would think about that? Or that she’s Shiv’s godmother? She probably used to help me tie my shoes when I was a little kid — and now we’re fucking. That’s why. I think if at any point Gerri turned to him and said, ‘Take off your pants, let’s fuck,’ he’d be like, ‘No, no, Mama!’ and run.”

There is a game the Succession writers play. It’s called Dangerous Bangers. Culkin credits it with finally allowing him to relax around his boss, Armstrong. “Jesse’s lovely,” Culkin says. “But for whatever reason, I couldn’t break down that wall, and I always felt a little bit intimidated by him. And I hate that because I like to feel I’m never intimidated by anyone.”

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Top: Culkin with Succession co-star J. Smith-Cameron, who calls him “one of the most available, alive actors I’ve ever worked with.” Bottom: In the 2002 breakout Igby Goes Down. Right: With wife Jazz Charton. Peter Kramer/HBO; United Artists, Courtesy Everett Collection; VALERIE MACON/AFP via Getty Images

So amid the New York City lockdown, Armstrong and his fellow writers Tony Roche and Lucy Prebble invited Culkin and Snook to join them in a round of Dangerous Bangers. Here’s how it works, per Culkin: “You introduce the group to watch what you think is a fucking banger — a great movie. But it’s a dangerous banger because you haven’t seen it in a while, and the group reaction might be that it’s a really shitty movie.” Culkin chose Big Trouble in Little China. (A banger.) Prebble chose L.A. Story. (Also a banger.) “Playing Dangerous Bangers with Jesse made me feel like, ‘I don’t know why I’ve been so fucking scared of this guy,’ ” Culkin says.

“I’m embarrassed,” Armstrong later admits of one of his own Dangerous Bangers entries. “It was kind of a highfalutin choice. But it was The Battle of Algiers,” he says, referring to the 1966 neorealist classic. “I’m afraid, on the very, very, very brutal terms of the rules for Dangerous Bangers, it was a failure — because I think at least one of the players fell asleep. That’s a fail.” Armstrong had better luck with a 1997 Nicolas Cage outing: “Con Air proved to be a genuine Dangerous Banger. It holds up. There was no sleeping. We were all very impressed with Con Air.”

Culkin tells me all this as Midnight shows us the bowels of Smith & Wollensky, which runs beneath Lexington Avenue. There’s a dry-aging room. A wine cellar. Pails of congealed fat. It’s all a bit fuzzy, as we’re several drinks in and are moving faster than we did at the Natural History Museum. Suddenly we’re back upstairs in a different bar in a different room — maybe even a different restaurant. “That guy’s name is Kieran too!” Midnight says, pointing to a bartender polishing a beer glass. The two Kierans wave to each other.

“What’s next?” I ask Culkin, during a quiet moment of contemplation.

“Let’s go to The Cock downtown,” he says.

“I mean what’s next for your career?”

“Oh,” he says. “My agents, who are relatively new to me, sent me four scripts, and it was taking me a while to read them. I was like, ‘You have to understand. We’re moving houses and there’s a baby that’s imminent, and I’m primary care for a toddler in the meantime. I think I’m going to call this paternity leave.’ They got it.”

Moments before we part ways around 11 p.m. on a busy New York street corner, Culkin shares one more story, about a friend, also an actor, who recently gave him what he felt was some excellent career guidance.

“He told me this: ‘If you say no, that’s fine — life carries on and you’re fine. But if you say yes, all this … stuff … happens.’ And I was like, ‘That’s really good advice!’ And he goes, ‘That’s what you told me.’ Apparently, I had given him that exact advice a year ago. I forgot. And I was like, ‘Shit, I don’t ever take my own advice.’ ” Then he hails a cab and disappears into the night.

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This story first appeared in the Oct. 6 issue of The Hollywood Reporter magazine. Click here to subscribe.