Kieran Culkin’s Career Evolution: From Humble Beginnings To Oscar Recognition

A run through the journey of Kieran Culkin’s to the Oscars

Kieran Culkin on Sunday capped a remarkable year by winning the Oscar for best supporting actor for his work in A Real Pain, a bittersweet look at family, friendships and Jewish loss stemming from the Holocaust.

The 42-year-old Culkin, the frontrunner throughout Hollywood’s awards season bested Yura Borisov Anora, Edward Norton A Complete Unknown, Guy Pearce The Brutalist and Jeremy Strong The Apprentice.

Since January 2024, Culkin has won an Emmy for the final season of HBO’s media family drama Succession on which he starred with Strong and a pile of trophies for this film role including a Golden Globe, Critics Choice award and Screen Actors Guild Award.

“I have no idea how I got here. I’ve just been acting my whole life. It’s just been a part of what I do,” Culkin told the audience, thanking his director, writer and co-star Jesse Eisenberg. 

“Thank you for this movie. You’re a genius. I would never say that to your face. I’m never saying it again,” Culkin said.

A Real Pain follows estranged cousins Benji (Culkin) and Dave (Eisenberg) as they go on a so-called heritage tour of Poland to learn more about the early life of their grandmother, who survived the Holocaust. Free-spirited Benji has been somewhat lost since the grandmother died, and is hoping to rekindle his childhood friendship with David, a neurotic New Yorker with a partner, a child and 1,000 worries. 

Culkin’s performance is both subtle and showy, as Benji swings from sentimental and considerate to explosive and unhinged. The pair’s relationship plays out against the backdrop of a concentration camp and outings with their fellow tour takers.

“I connected with the character immediately, which almost never happens,” Culkin told AFP at the film’s premiere at Sundance in early 2024.

“I think it’s happened three times ever in my life,” including his beloved role on Succession as Roman Roy, he added.

In December, Culkin told The New York Times: “I just wanted to show up and not rehearse and not think about it because the character’s spontaneous and surprising.”

Eisenberg told USA Today that he cast Culkin who is not Jewish after his sister read the script and suggested the actor was the right fit.

Culkin brought his “unusual energy” and “great sense of timing and intelligence” to filming, Eisenberg told AFP last month in an interview in Paris.

Born on September 30, 1982 in New York into a family of seven siblings, Culkin started acting as a child and made his film debut as the cousin of Kevin (played by his brother Macaulay) in the 1990 Christmas classic Home Alone.

After turns in Father of the Bride (1991) and the less-well-received Home Alone 2: Lost in New York, the following year, the diminutive, dark-haired actor took a variety of film, television and stage roles.

His critical breakthrough would come in 2002 with coming-of-age flick Igby Goes Down opposite Claire Danes, Bill Pullman and Susan Sarandon. The role earned him a Golden Globe nomination, but also sent him running from Hollywood.

Culkin took roles on the stages of London’s West End and Broadway, including in two plays by Kenneth Lonergan. Eisenberg has said that pedigree is in part what led him to call about A Real Pain.

A series of small parts followed, including a memorable one in Scott Pilgrim vs the World (2010) and several forgettable ones.

All that changed when he was cast as Roman Roy in Succession, a saga charting the back-stabbing dynastic squabbles of an ultra-wealthy family that debuted in 2018 to popular and critical acclaim. The series wrapped in 2023. 

Culkin earned an Emmy, two Critics Choice Awards and a Golden Globe for the role.

The actor, who is married with two children, will next be the voice of Squealer in Andy Serkis’ animated adaptation of George Orwell’s Animal Farm, expected to be released this year, according to IMDb.

Despite all the accolades of the past year, he told The New York Times that he acted to live, and not the reverse.

“That stuff is nice, but the real stuff is me being home with my kids, when I’m reading them books and singing them songs until they go to sleep. That’s the whole point of life. The rest of it I’m doing so I can get back to that,” he said.