We have been refused.
But his spirits are not dimmed.
Be honest, he prompts me.
FEELING ITThe Emmy award–winning Culkin has two young children—and likes to say they are his sole accomplishment. Ferragamo sweater. Sittings Editor: Max Ortega. Photographed by Norman Jean Roy.Vogue, October 2024.
Isnt it kind of fun to be rebuffed?
Culkin is wearing a black short-sleeve shirt and sneakers.
He has a bandana looped around his wrist.
LOOKING BACKInA Real Pain,opening in theaters November 1st, Culkin stars opposite Jesse Eisenberg as two cousins on a grief-driven tour through Poland. Coach blazer and pullover.
I have on a jean jacket and Birkenstocks.
Culkin clasps his hands together in anticipationanother rejection!
We debate the merits of elite restaurants.
MR. HAPPYHermès blazer and sweater.
Im not a decisive person, Culkin tells me as tabs proliferate on his phone.
Fifteen minutes later, we walk into Keens.
He has not been onscreen since the finale aired in 2023.
But here comesA Real Pain,the sophomore feature from actor-filmmaker Jesse Eisenberg.
When Charton met Culkin, he was an avid indoor rock climber.
He has since swapped bouldering for clambering on playground equipment.
He has emblazoned his phone case with a sticker from his daughters swim class.
(Theres also a decal of Keanu Reeves, because Charton loves him.
But who doesnt love Keanu?
Culkin wants to know.
Lets get fucking real.)
Coach blazer and pullover.
Kierans first role was inHome Alone,where he was cast as a cousin to Macs Kevin McCallister.
He was eight at the time and has held on to some measure of fame ever since.
But like the inheritance he chased as Roman onSuccession,it has turned out to be a complicated bequest.
He and his father, Kit, do not speak, an estrangement that goes back decades.
So when his departure date for Warsaw to start production onA Real Paindrew nearer, Culkin waffled.
He called her, prepared to break the news: He had to bail.
Eisenberg was in Poland, scouting locations; Culkin was due on set in a matter of weeks.
But Stone told him she understood and that she would deal with it.
Culkin thought he was being replaced.
She goes, If you dont do it, the entire movie falls apart.
But thats not your responsibility.
You shouldnt feel that burden atall.
Culkin marvels at her approach.
She was nice enough to let me off the hook, he says.
So I guess Im…in?
When he flew to Poland, Stone made sure she and her husband were on the same flight.
Eisenberg likens the choreographed airport travel to a hostage swap.
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It wasnt untilA Real Painpremiered at Sundance that Eisenberg learned just how close Culkin had come to defecting.
I was infuriated, Eisenberg tells me.
Most actors work for validation.
Culkin works despite his natural inclination.
Both men acknowledge that filming got off to a rough start.
Culkin was used toSuccession,where creator Jesse Armstrong presided over a very, very loose process.
Eisenberg had blocked the entire film before his fellow actors stepped on set.
The trouble started within the first few hours.
Eisenberg indicated to Culkin where he was meant to stand.
Culkin felt the position was off.
Jesse goes, Well, it doesnt look weird, Culkin says.
And I was like, What I do, I have to feel.
He was brilliant, Eisenberg says.
But I still dont understand how he thinks or works.
You stop questioning these things, Eisenberg says.
Kieran was just exhilarating and constantly baffling.
I was in panic mode the whole time, he says.
I just went to this horrible place.
I was just so fucking broken, he says.
Jesse was like, Whats wrong with you?
Culkin shakes his head.
Tons of actors miss their kids.
For him, the experience was destabilizing.
It was around this time that he met the actor Alison Pill.
Like him, she was immersed in the downtown theater world and living in the East Village.
The two would cap off their adventures at the dive Bar None.
It was frustrating, she says.
Its like, Youre getting all these opportunities.
He didnt answer emails.
He is still often inaccessible to his agents, Pill says.
Culkin was 26 and beginning to think about acting as something more than the family business.
He wanted to do the movie.
He wanted to grieve.
He blew past all the deadlines.
A month later, he texted Pill: Had production started?
Wright stepped outside and spoke to Culkin for 10 minutes.
Culkin got on a plane and made it to set the next morning.
In retrospect, he wonders if it was the best decision.
The movie is one of his favorites and the role was tailor-made for him.
But he had not intended to work through his devastation.
InA Real Pain,Benji models the alternativenot just to feel sorrow but to let it overtake him.
Would that have been healthier?
Ive never seen someone grieving and thought, Boom, nailing it, Culkin says.
He clawed out of that acute period of sadness.
But I didnt know how to process it, he says.
Im still working on that.
He met Charton in a bar in 2011.
Charton was at a table with another man, who rose and left after a few minutes.
Culkin took his vacated seat and asked, Was that your boyfriend?
When Charton told him no, he introduced himself.
Id never been that forward, he says.
I had never, ever until that moment just approached a woman.
The two eloped on a road trip in 2013.
Charton packed her J.Crew wedding dress in the trunk.
If in the last decade Culkin has seemed more at ease, Pill credits Charton.
She has given him a harbor.
In front of an audience, he is an artistalive and spontaneous and inventive and free, Cera says.
But reading the pilot, Culkin felt drawn to Roman and submitted tapes for that part on a whim.
MR. HAPPYHermes blazer and sweater.
Culkin is grateful but doesnt suffer the same confusion; hes clear on what separates him from his characters.
Romanthats a pretend guy, he says.
(He has not heard it.
He is relieved to hear the Swifties dont hate him.)
Still, the end ofSuccessiondid affect him.
I think he loves it, he says.
Thats some peoples bread and butter.
AfterA Real Pain,Culkin and Charton took their first vacation since the kids were born.
WhenSuccessionearned him an Emmy in January, he used his speech to pitch Charton on having a third child.
A mistake, in retrospect: I was getting close to her agreeing and I fucked it.
He has learned his lesson and will not use this interview as a platform for the cause.
He cooks way more than me, Charton says.
He goes out of his way to prepare these meals that I know they wont touch.
A sophisticated roast chicken was recently forsaken in favor of french fries.
He has been sent about 50 subpar film and TV treatments over the past six months, he says.
None have tempted him.
(It helps that producers agreed to switch up the schedule to accommodate Sundays with his children.)
Wed be like, I want to be a cowboy, Culkin says, miming tiny finger guns.
Or like, I want to play a character who has a mustache.
The truth is he just wants to land good parts in good projects.
If he is going to submit himself to the grind, it has to be worth it.
And he readies his backup plan.
I keep thinking Ill play the lottery, he says.
But isnt that the rub?
In this story: grooming, Amy Komorowski.
Produced by Boom Productions.
