Sean Penn Wins 2nd Big Oscar of the Night — But ‘Couldn’t Be Here… Or Didn’t Want To!’

Legendary actor Sean Penn won the second major award of the 2026 Oscars — but presenter Kieran Culkin accepted on his behalf.

The Academy of Motion Picture Arts and Sciences held their 98th annual Oscar Awards Show on Sunday night, and viewers watched with the usual anticipation or dread that politics would rear its head during the festivities.

It didn’t take very long, with references to the Epstein Files and the turmoil in the country during the host’s monologue. But after the commercial break, O’Brien snuck in a dig at Trump over his propensity for naming things after himself.

There were also some awards to give out, and Penn took the Best Supporting Actor trophy for his role in One Battle After Another.

Culkin accepted the award with a little ad-lib:

KIERAN CULKIN: And the Oscar goes to Sean Penn, One Battle After Another. Sean Penn couldn’t be here this evening, or didn’t want to, so I’ll be accepting the award on his behalf.

The actor recently slammed the Oscars at a press conference at the Marrakech Film Festival.

“The Academy have exercised really extraordinary cowardice when it comes to being part of the bigger world of expression, and in fact, have largely been part of limiting the imagination and very limiting of different cultural expressions,” Penn said.

He added:

Ceremonies like the Oscars should best be seen as “television shows first” and less as barometers of artistic merit, he continued.

“So I don’t I get very excited about what we’ll call the Academy Awards [except for] when a film like ‘The Florida Project,’ or ‘I’m Still Here,’ or, you know, ‘Emilia Perez,’ of the things that are likely to happen this year,” he added. He also weighed in on the controversy over Ali Abbasi’s “The Apprentice,” saying “when something sneaks through, it’s to be celebrated.”

“It’s jaw-dropping how afraid this [so-called] business of mavericks is of a great film like that. One with great, great acting. [It’s amazing] that they too can be as afraid as a piddly little Republican congressman,” he said.

The other nominees in Penn’s category were:

• Benicio Del Toro for One Battle after Another
• Jacob Elordi for Frankenstein
• Delroy Lindo for Sinners
• Stellan Skarsgård for Sentimental Value

Watch above via ABC and The Oscars.

New: The Mediaite One-Sheet "Newsletter of Newsletters"
Your daily summary and analysis of what the many, many media newsletters are saying and reporting. Subscribe now!