Kieran Culkin has officially added an Academy Award to his growing collection, winning Best Supporting Actor for his role in A Real Pain. But instead of a traditional speech, he turned the moment into a hilarious callback to a promise his wife, Jazz Charton, once made — a promise she never expected to fulfill.
Culkin reminded the audience of a conversation he had with Charton after winning an Emmy in 2024 for Succession. At the time, she had jokingly promised another child if he won — only to realize later she had actually said it. "After the show, we’re walking through a parking lot … and she goes, 'Oh, God, I did say that!'" Culkin recalled. "I guess I owe you a third kid."
But Culkin had bigger plans. "I turned to her and said, 'Really, I want four.' And she told me, 'I will give you four when you win an Oscar.'" His wife laughed and simply replied, "No".
A Winning Season with Unscripted Speeches
Culkin’s Oscar win capped off a dominant awards season, where he won at the Golden Globes, BAFTA, SAG Awards, Critics Choice Awards, and more. His spontaneous, often self-deprecating speeches became a highlight of the season — so much so that Robert Downey Jr., who presented his Oscar, jokingly told him: "If you’d simply cease trying to be as witty as me, you’d be perfect."
At the SAG Awards, Culkin even took a jab at Adrien Brody for his lengthy speech: "I don’t think anyone can hold this for 45 seconds — which is the allotted time, Adrien Brody!" before quickly adding, "No reason to take that shot. I love you. Take your time."
An Almost Missed Opportunity
In A Real Pain, directed by Jesse Eisenberg, Culkin plays a charming yet exasperating man touring Holocaust sites with his cousin. His performance blends dark humor with emotional depth—something he almost never got to showcase.
Weeks before filming, Culkin considered dropping out because he didn’t want to be away from his family for a month. Emma Stone, a producer on the film, convinced him to stay, using what Culkin later described as "savvy emotional blackmail."
From Child Star to Oscar Winner
Culkin’s career began in childhood, with early roles in Home Alone (alongside his brother Macaulay Culkin), Father of the Bride, and Music of the Heart. His breakthrough came in 2002’s Igby Goes Down, but it was his role as Roman Roy in Succession that made him a household name. Now, with an Oscar in hand, Culkin has not only cemented his status in Hollywood but also turned his victory into one of the funniest moments of the night.
And while his wife may have shut down the idea of baby number four, one thing is clear — Kieran Culkin knows how to own the stage.
