His road to the Academy Awards started in New York where he was born and raised in the city. As for his first big break? That came at just 8 years old when he was cast alongside his brother in "Home Alone."
He then went on to be in movies like "Father of the Bride," "She's All That," and "The Cider House Rules." Those roles were all long before he landed the impulsive, cruel and entitled Roman Roy on the hit show "Succession."
It's a role that won Culkin an Emmy and a Golden Globe, but it didn't actually help him land the part that's currently all the buzz: Benji Kaplan in "A Real Pain."
It turns out the movie's writer, director and co-star Jesse Eisenberg only knew Culkin's work from "Home Alone," but he followed his gut and it certainly paid off.
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"A Real Pain" is inspired by Eisenberg's own story and it follows mismatched cousins touring Poland to honor their land grandmother.
For fans of "Succession," Benji shares Roman's frantic and unpredictable energy, yet somehow, irresistible charm.
"He doesn't have any lasting relationships, he had one with his grandma who's gone, the only other lasting relationship he has is with his cousin and they can't really seem to connect anymore at this age with their different places they are in their life," Culkin said.
And Eisenberg said the two co-stars' dynamic off-screen is pretty similar to on-screen.
"He grabs me by the face, drags me around the room, makes fun of my outfit and hair, pretty much a mirror image of what you see in the movie," Eisenberg said.
Eisenberg said it has been wonderful to see Culkin getting praise for the role.
"Oh, it's the greatest thing in the world," Eisenberg said.
In an era of blockbusters and franchises, "A Real Pain" is film you don't see being made much anymore.
"Somebody put it as a light film with a heavy heart and I like that," Culkin said.
It's a story about family, connection and healing - with a performance that could see Culkin adding an Oscar to his collection.