Actor Kieran Culkin, who presented the award, accepted the award on the Milk star’s behalf, but not before cracking a cheeky quip about Penn’s absence.
“Sean Penn couldn’t be here this evening… or didn’t want to. So, I’ll be accepting this award on his behalf,” he told the audience.
Indeed, it looks like Penn opted out of attending the prestigious award ceremony of his own volition. While the actor did not announce he would be missing the Oscars in the lead-up to the event, Penn pointedly skipped both the BAFTA Awards and Actor Awards in recent weeks, two ceremonies where he also won for best actor in a supporting role.
READ MORE: Oscars 2026: The Full List of Winners
Penn has had a prickly relationship with awards shows over the course of his career, often for political reasons. In 2023, he admitted he had considered melting his two Oscar trophies to provide ammunition metal for Ukraine.
“I thought, well, f–k, you know? I’ll give them to Ukraine. They can be melted down to bullets they can shoot at the Russians,” Penn told Variety at the time.
Penn revealed he ended up giving one of his Oscar trophies to Ukraine’s president Volodymyr Zelenskyy. “I told him to keep it and bring it to Malibu after all this is over and his country is safe,” he shared.
This isn’t the first or only time Penn has skipped the Oscars. The Hollywood star also skipped the 1996, 2000, and 2002 ceremonies, where he was nominated for Best Actor for his roles in Dead Man Walking, Sweet and Lowdown, and I Am Sam, respectively.
Penn won his first Oscar for Best Actor for Mystic River in 2004, followed by a second for his role in Milk in 2009.
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