On March 2, 2025, Kieran Culkin cemented his place in Hollywood history by winning the Best Supporting Actor award at the 97th Academy Awards for his standout performance in A Real Pain.
The film, a poignant dramedy directed by Jesse Eisenberg, has been a critical darling, and Culkin’s portrayal of Benji Kaplan—a free-spirited, emotionally raw character navigating a Holocaust tour in Poland alongside his cousin (played by Eisenberg)—earned him his first Oscar nomination and win.
At 42, Kieran Culkin’s age belies the depth of his career, which spans decades and includes iconic roles like his stint in Home Alone and his Emmy-winning turn in Succession. But it’s A Real Pain that has thrust Culkin into the spotlight like never before, sparking conversations about his talent, his family, and his unforgettable Kieran Culkin Oscar speech.
From Home Alone to Hollywood Heavyweight
Born into the Culkin family, Kieran—brother to Macaulay Culkin, the Home Alone child star—has long been a familiar face in the industry. While Macaulay Culkin’s brother made his mark as Kevin McCallister (with Kieran appearing as cousin Fuller in the same film), Kieran carved his own path through indie films and television.
His early role in Kieran Culkin’s Home Alone was a nostalgic footnote, but his career trajectory took a sharp upward turn with HBO’s Succession, where he played the sharp-tongued Roman Roy. That role earned him critical acclaim, multiple awards, and a fanbase eager to see more of Culkin Kieran.
Yet, A Real Pain—sometimes misspelled as A Real.Pain or Real Pain—marks a new pinnacle. The movie, co-starring Edward Norton (himself no stranger to Oscar nominations) and produced by Zoe Saldaña (often written as Zoe Zaldaña), explores grief, identity, and familial bonds with a mix of humor and heartbreak.
Culkin’s Benji is the chaotic counterpoint to Eisenberg’s reserved David, and critics have hailed his performance as a career-defining moment. The film’s success at the 2025 Oscars, with Culkin’s win, underscores its impact, making A Real Pain movie a must-watch and a standout in Jesse Eisenberg’s movies.
The Kieran Culkin Oscar win wasn’t just about the trophy—it was about the moment. Taking the stage at the Dolby Theatre, Culkin delivered a speech that was equal parts heartfelt and hilariously unfiltered.
He gave a shoutout to Jeremy Strong, his Succession co-star and fellow nominee for The Apprentice, saying, “Jeremy, you’re amazing in The Apprentice. I love your work. It’s f***ing great.” The expletive was bleeped out on the US broadcast, but the sentiment—and the subsequent reveal—lit up social media. Fans of Jeremy Strong’s movies and TV shows noted the camaraderie, a nod to their Succession days.
Then came the personal twist. Turning to his wife, Jazz Charton, Culkin quipped, “I promised my wife that if I won an Oscar, we’d have another kid. So, Jazz, let’s get cracking on those kids, what do you say?” The crowd erupted in laughter.
Kieran Culkin’s wife, a former model, has been his partner since 2013, and the couple already shares two children: Kinsey Sioux (born 2019) and Wilder Wolf (born 2021). How many kids does Kieran Culkin have? Two, for now—but the Kieran Culkin kids count might grow if he keeps his word.
Family Affair
The Culkin name carries weight in Hollywood. Kieran Culkin and Macaulay Culkin share a bond beyond their Kieran Culkin siblings status—both have navigated fame from a young age.
While Macaulay Culkin’s Oscar dreams remain unfulfilled (he’s never been nominated), Kieran’s win has sparked speculation about a friendly sibling rivalry. Notably absent from his speech was any mention of Macaulay, which some outlets found surprising given their closeness. Still, Kieran’s victory stands on its own, a testament to his evolution from child actor to awards-season titan.
The Culkin movie legacy isn’t limited to the brothers. Kieran’s work in A Real Pain aligns with his knack for choosing complex, character-driven projects—think Igby Goes Down or Kieran Culkin movies like Scott Pilgrim vs. the World. His collaboration with Ed Norton (another heavyweight with Edward Norton Oscar nominations) and Eisenberg only bolsters his reputation as a serious actor.
A Real Pain
A Real Pain isn’t just a vehicle for Culkin’s win—it’s a film that resonates. Written and directed by Jesse Eisenberg, it follows two cousins grappling with their grandmother’s death and their Jewish heritage on a trip to Poland. Ed Norton plays a tour guide, adding gravitas, while Zoe Saldaña’s producer role ties it to her growing influence in indie cinema.
The movie’s blend of humor and melancholy has drawn comparisons to The Grand Budapest Hotel, but its emotional core is uniquely its own. For Culkin, Kieran Culkin’s A Real Pain* role as Benji—a man wrestling with pain beneath a playful exterior—mirrors the wit he brought to Succession while showcasing new depth.
The A Real Pain Oscars buzz didn’t stop at Culkin. The film earned nominations in other categories, though his Best Supporting Actor 2025 win was the night’s highlight. It’s a far cry from his Kieran Culkin in Home Alone days, proving he’s no longer just Macaulay Culkin’s brother.
What’s Next for Kieran Culkin?
Culkin’s sweep of the awards season—Golden Globe, BAFTA, SAG, and now Kieran Culkin’s Oscars—has raised the bar. Unlike Emma Stone’s Oscar wins, which span multiple categories, Culkin’s first taste of Academy gold feels like a launchpad.
Will he return to TV, perhaps revisiting the Succession universe? Or will he chase more cinematic roles like The Real Pain movie? His Kieran Culkin awards haul suggests he’s got the clout to choose.
For now, the focus is on Kieran Culkin’s children and his life with Jazz Charton. At 42, Keiran Culkin (as some misspell it) balances stardom with fatherhood, a dynamic that endeared him to fans during his speech.
Whether he’s cracking wise about Jeremy Strong, teasing about expanding his family, or reflecting on A Real Pain, Kieran Culkin remains a singular force—one who’s finally getting his due.
In a year where Edward Norton, Jesse Eisenberg, and Zoe Zaldaña brought their A-game, it’s Culkin Kieran who walked away with the statue. From Succession to A Real Pain, his journey is a masterclass in reinvention—and a reminder that sometimes, the supporting actor steals the show.