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For Kieran Culkin, the Best Endings Are the Difficult Ones

Culkin doesn’t need his shows and movies to be tied up in neat little bows (except when he does). Instead, Roman Roy’s real-life counterpart prefers complexity—much like ‘Succession’ itself.

HBO/Getty Images/Ringer illustration

It was only when a Succession clothier bid adieu to him last week that Kieran Culkin, who plays Roman Roy in the HBO series, understood it was really, truly over. “Last night was sort of the first, like, ‘Oh wait, actually this is goodbye,’” Culkin tells The Ringer over Zoom the day after the red-carpet premiere for the show’s fourth and final season. “I said goodbye to Danny [Mura],” Culkin says, “who’s my costumer on the show and has been since pretty much the beginning.”

This might have been just another unexceptional exchange between two colleagues if it wasn’t such a rare one. “He usually does an Irish goodbye,” Culkin says, lovingly. “But he was like, ‘I didn’t do it this time because I’m saying goodbye.’ I was like, that’s nice! He goes, ‘Because this is it.’ And I went, ‘Oh man, this is it.’ It’s sort of brutal!”

Over the course of Succession’s first three seasons—featuring a big bathroom break along the way—Roman has gone from being the snide and malicious (and only theoretically grown-up) youngest Roy brother to being the snide yet increasingly discerning (and concerned) potential ascendant to the whole family throne.

Sure, last season, Roman’s sly rise was stalled by his own boneheaded risqué slip. And yes, in the Season 4 premiere, he could still be found doing childish things like reflexively calling shotgun. But in the same episode, Roman was also the only one of the Big Three Roysibs (sorry, Connor) to call out the absurdity of their too-many-billions bid for Pierce Global News. He was the only one willing to call horse potatoes, albeit ever so briefly, on Nan Pierce. And he was the only one to point out, however richly, that he was no longer interested in the ironic: He seeks the iconic.

As the acerbic, brisk Succession rounds the quarter pole into its final season, Culkin-as-Roman continues to demonstrate intriguing potential in the Roy family horse race—that is, if he doesn’t keep dicking around.

Culkin, 40, first received a script for Succession back in 2016, when, for a hot minute, he was under consideration for the role of Cousin Greg. (Around the same time, Jeremy Strong was interested in playing the role of Roman. Imagine!) Culkin wound up being one of the first people that showrunner Jesse Armstrong officially cast—as Roman—and he has been a core member of the Roy family ever since.

Roman Roy is a repressed loudmouth and a crass clown; he is a cowering wallflower and a towering asshole. He is a walking defense mechanism and an offensive crank yanker; he gets off on shame and is also held back by it. “You know, you’re fucking great,” Roman tells Tabitha when he starts seeing her in Season 1. “You’re not a head fuck. Or a bitch. Or a leech.” Ooh la la!

He botches rocket launches and phone sex. He boosts crypto-fascists and shrinks in the presence of emails and accidentally deployed dick pics. He is a poet who says things like “dildo dipped in beard trimmings” to describe another man (sorry, Stewy!) and “We’ve never licked his big omelet nipples” about his own father. He displays more potential for empathy than pretty much anyone else in his family—though that’s an exceedingly low bar.

The character and performance seem to be the ideals for Succession, where Armstrong famously encourages actors to improvise and blurt out whatever weird rubbish flows through their minds. But while Culkin has come to excel at this approach, it proved difficult for him at first. In a recent interview with Esquire, he recalled feeling terrified when, during one of his first days on set, he heard Armstrong direct Alan Ruck to start riffing off-script. In another story from The Hollywood Reporter, Culkin said that he was a little bit afraid of Armstrong for years. (It was only when they played a made-up movie-based game called “Dangerous Bangers” that he felt more chill.) Now, just in time for the show to come to an end, he’s become seasoned in the art of spontaneity. Writer Georgia Pritchett told Newsweek that the line “Well, these hands aren’t going to fuck themselves” was all Culkin.

“The only reason I’m able to do it is because I was there from the beginning when we were discovering it,” he says. “I think if I were thrown into the show like Season 3 or 4, I don’t think I would’ve survived.”

Culkin brings up a plot point in Season 2, where Roman freaks out when given an assignment during a Waystar Royco management training class and sputters: “This is everything! This is rank and yank! Up or out!” To Culkin, that’s how performing on Succession could sometimes feel. “And I don’t think it’s designed intentionally for that,” he says. “But there is a sink-or-swim, rank-and-yank thing that does happen here. You come on the show, it is a lot to take on, but if you can fuckin’ swim, then …”

He gives an example: Zoe Winters, who plays Kerry, Logan’s much younger business/personal companion. “She came in very last minute as, like, an assistant,” Culkin says. “And she was great. Like, she was just there, and she had one or two lines in her first day, and we just started throwing things at her, and she just would have responses. She just had stuff at the ready and was very much with us. And we all talked about how we thought she was great, and then they gave her more to do. And that’s sort of what the show does. … Suddenly, the character of Kerry has a much bigger part.” You don’t get to omelet nipples unless you’re willing to crack a few jokes along the way.

Another guest star whom Culkin immediately worked smoothly with was Alexander Skarsgard, who plays the once-stoic, now-skeptical Swedish magnate Lukas Matsson, the head of tech company GoJo. “Our first scene together was a scene where we go into the urinal and pee on my phone,” Culkin says about one memorable meeting of the minds last season. “And we did a rehearsal, and it just went really well. They were like, ‘Let’s get the cameras up. Cameras will be ready in like five minutes.’” Lorene Scafaria, who was directing the episode, asked Culkin how long the two actors had known each other.

“I said, ‘Just now. We just met in that rehearsal in the urinal,’” recalls Culkin. “I felt like he knew his lines; I knew mine. We had ideas, and it just, like, worked right away. And he was a guy who came in on his first day and understood the language of the show and knew how to just play. He wasn’t, you know, scared by it.”

While Matsson didn’t appear in the season’s opening episode, various Season 4 trailers suggest a forthcoming showdown—in what looks like extremely Nordic terrain—between the two actors. “We are gonna grind you down, man,” Roman says in one of them. “We are sand in the gears.” In another, Matsson taunts him: “You just fucked yourself.” In Succession, such words could signify a vast range of outcomes, from secret new alliances to market-moving levels of loathing to a consummated deal to a total blood feud.

When it comes to Roman, it feels like the biggest looming question is: Whom might he betray? There are, for example, signs that he might peel away from the “rebel alliance” currently comprising him, Kendall, and Shiv. Already in Season 4’s first episode, Roman was noticeably more ambivalent than his siblings about the acquisition price for Pierce; could that undercut their solidarity? (“You do know what half a billion dollars is, right?” he asks when Kendall and Shiv want to bump up their bid for the legacy company. “Five hundred times a thousand thousand dollars of actual money that we could be spending on fucking snowmobiles and sushi.”) If Logan does wind up reeling Roman back into his cutthroat inner circle, what grim test of loyalty might he then require? It isn’t hard to imagine Roman having to backstab, say, a brother (Logan does call him Romulus) or even Gerri to prove himself to his dad. Logan has always been adept at pressing those messed-up buttons.

With Succession set to wrap up its whole existence, Culkin is torn on what constitutes an ideal ending, broadly speaking. “It’s more that I can tell you the ones I don’t like,” he says. “Whenever I feel like a story has a really nice little bow on it, I tend to not like that. I was just describing this to someone the other day …”

He starts venting about the end of a video game he recently finished that involves multiple characters. (I’ll keep it nameless to avoid spoilers.) “There’s one character in particular that’s completely in the right,” he says. “And by the end of the game, they’re fighting each other, and the one that you like is underwater, and you have to drown them. The game is forcing you to. You have to tap the button or the game doesn’t continue on.” As he tells it, he was basically tearing up as he tapped the button. “I was like, ‘I don’t want this character to go.’”

But then the character didn’t go! At the last second, the game lets them live. “I was relieved and then immediately disappointed,” Culkin says. “I think what they were making me do was so manipulative. It was very emotional! And they got me, and I was like—if they’d followed through, I probably would have, like, thrown the controller and cried and been like, ‘This game is brilliant because they made me do this thing.’ Instead, they released me, and they put a nice little bow on it.”

But on the other hand, he says, searching back through the archives of a mind that has seen and been in a hell of a lot of productions, some of his favorite pieces of work—like The Princess Bride or Howl’s Moving Castle—have “very much nice endings. … They just fly off to the clouds!” Whether Succession finishes its journey by landing the plane gently or by riding off into oblivion, it’s likely that the experience of watching it will feel turbulent either way.

“You know, there’s a promise in the title of Succession,” Armstrong told The New Yorker when he announced that this season would be it. “I’ve never thought this could go on forever. The end has always been kind of present in my mind.” For Roman’s character, the end could mean certain victory, however Pyrrhic, over the markets or the peons or his father or, hell, his mother. (Unlikely: Caroline might be the most invincible boss there is.) Or it could deliver all the snowmobiles and sushi a guy could dream of, enough to feel more like a nightmare. “I want the ending I don’t want,” Culkin says.

If the going-on-four seasons that came before it are any indication, that ending ought to only further invigorate Culkin’s career. In an interview for the Esquire cover story that came out this week, Culkin said he didn’t really have that many specific projects ahead of him, with the exception of a Jesse Eisenberg–helmed picture called A Real Pain. Culkin acknowledged that frequent Succession (and Game of Thrones and The Menu) director Mark Mylod had also bandied about a future idea in which Culkin plays the protagonist in an action movie—a concept he definitely wasn’t opposed to, even if he found it amusing. (“Who the fuck would buy that a 140-pound, 5-foot-7 guy could start kicking some ass?” he told Esquire.)

Regardless of where he goes next, Culkin will retain some vestiges of Roman Roy—like, for example, the wholly unholy character’s vestments. During a visit to The Late Show With Stephen Colbert last August, Culkin confessed that not only had he come straight from the Succession set, but he was also still wearing pieces from his Roman Roy wardrobe, because all of his civilian clothes were “oversized things with, like, avocado smeared on it.” I ask Culkin what he’d do in the post-Succession era in a similar situation.

“Yeah, well, maybe some of Roman’s suits fell off the truck, and I happened to pick them up and bring them home, so I think I’ll be good,” Culkin replies. He looks a lot like his Succession character as he says this, with his floppy bangs and mischievous squint and Roy-al smirk. On the show, that swagger can be awfully deceiving; over three-plus seasons, the blustering Roman has used his caustic charisma as an inhuman shield time and again. Culkin, on the other hand, has actually pulled off a meaningful acquisition, stockpiling assets that can outlast all the goodbyes and that are tailored to his every whim. When you get used to the really good stuff, it’s hard to ever let it go. Just ask anyone with the last name Roy.