Bill Murray Still Can’t Believe He Lost an Oscar to Sean Penn

The Lost in Translation star opens up about his unexpected awards season twist.

Bill Murray has been popping up in the headlines lately. First, a past on-set clash with Lucy Liu made the rounds again, and now, he’s back in the news for reflecting on one of Hollywood’s biggest what-ifs—his 2004 Oscar loss.

In an interview with The Howard Stern Show, Murray admitted that he was genuinely surprised when Sean Penn took home the Academy Award for Best Actor for Mystic River instead of him. At the time, Murray had been sweeping the awards circuit with his performance in Lost in Translation, winning a Golden Globe, a BAFTA, and an Independent Spirit Award, among others. That level of momentum tends to create a certain expectation, and as it turns out, even Bill Murray isn’t immune to that mindset.

"It was sort of surprising. I won every other prize for Lost in Translation, so I just sort of thought I was gonna win, 'cause I'd won everything — every single one," he said.

This wasn’t just another moment of celebrity self-reflection—it was a rare glimpse into how even the most laid-back, seemingly unbothered actors can get caught up in the industry’s unspoken rules. Murray described the feeling as a "low-grade virus," something that lingered for months before he was able to fully shake it off.

Losing to Sean Penn, who delivered a powerhouse performance in Mystic River, wasn’t exactly a shocker to anyone else. But in Murray’s case, the disappointment was less about the golden statue itself and more about realizing he had unknowingly started wanting it. And for someone with his effortless cool, that realization might’ve stung more than the loss itself.

Two decades later, he still hasn’t received another Oscar nomination. But let’s be honest—Murray doesn’t need a trophy to stay iconi