And the Oscar Goes to... Kieran Culkin!

Kieran Culkin winning an Oscar? Feels like something out of a fever dream—or, more accurately, something Roman Roy would joke about before immediately self-sabotaging. But here we are. And if there’s anyone who deserves the gold for effortlessly blending comedy, pain, and raw authenticity, it’s him.

At 42, Culkin has perfected the art of playing characters who are walking contradictions—hilarious yet heartbreaking, cocky yet deeply insecure, lovable yet completely insufferable. It’s a niche, but one he’s ruled over like a king (or, in Succession’s case, an emotionally stunted, foul-mouthed, pathetically tragic prince). He’s built a career out of portraying guys who pretend not to care while secretly drowning in existential dread, and in A Real Pain, he delivers what might just be his magnum opus.

A Real Pain, written and directed by Jesse Eisenberg, isn’t about the Holocaust in the way one might expect from a film set in Poland with two Jewish leads. It’s not a history lesson—it’s about grief, identity, and the complicated, messy ways we connect (or fail to) with our family. And it hinges on Culkin’s ability to sell a very specific kind of character: the one who won’t stop talking, cracking jokes, and making everyone around him uncomfortable because silence would mean acknowledging the gaping hole of sadness inside.

The man nearly didn’t even make it to set. Culkin has never been one to jump at every project thrown his way. In fact, he’s been vocal about how acting wasn’t always his first choice, and he’s spent much of his career debating whether he even wanted to be doing this at all. Before filming began, he almost walked away entirely. Enter Emma Stone, who, in a move that proves she should win an award just for being a great friend, flew to Poland with his family to keep him from bailing.

And thank god she did. Because according to Eisenberg, Culkin was delivering the best performances of his life without even realizing it. The guy wouldn’t even know what scene they were filming that day, skimmed the script, and then went on to absolutely demolish every take. That’s Kieran Culkin in a nutshell—chaotic, self-deprecating, and somehow always brilliant.

Succession fans have known for years that he’s got the range. As Roman Roy, he turned a perverted, emotionally crippled rich kid into one of the most fascinating, devastating, and darkly hilarious TV characters of the last decade. The way he injected pathos into a character who, on paper, should have been utterly detestable? That’s not just talent—it’s sorcery.

A Real Pain pushes him even further. It strips away the billion-dollar safety net and leaves us with something much rawer: a man forced to confront his own trauma and history without the armor of wealth, irony, or a Logan Roy-shaped shadow looming over him. It’s Culkin at his best—unfiltered, unpredictable, and utterly human.

So, is the Oscar his? Well, Hollywood loves a narrative, and Culkin’s got a damn good one. Child star turned reluctant actor turned guy-who-almost-ran-away-from-the-movie-that-might-win-him-an-Oscar? It’s the kind of full-circle arc that the Academy eats up. But even if he doesn’t take home the statue, one thing is clear: Kieran Culkin has already won. He’s cemented himself as one of the most compelling actors of his generation, proving that sometimes, the best performances come from the people who were never entirely sure they wanted to be here in the first place.