@rockmarooned Published March 15, 2026, 9:16 p.m. ET More On: Oscars 2026 ‘Two People Exchanging Saliva’ Director Loudly Booed After Dissing Timothée Chalamet Amy Madigan Confirms She and Zach Cregger Are Working On a ‘Weapons’ Prequel Starring Aunt Gladys: “I Trust Zach and He’s Got A Lot Of Whack Ideas In His Head” Dame Anna Wintour Publicly Embraces Her ‘Devil Wears Prada’ Reputation With Hilarious Oscars 2026 Bit With Anne Hathaway: “Thank You, Emily” Amy Madigan Accepts Oscar for Best Supporting Actress With An Evil Cackle, Thanks “All the Dogs” Best Supporting Actor felt like a genuine toss-up at this year’s Oscars right up until the point that Sean Penn’s name was called. He might have seemed like an unlikely choice, given that he already won Best Actor for Mystic River in 2003 and Milk in 2008. But if Academy voters like you, they don’t mind calling you back to the stage — even if you’re unlikely to actually show up. Penn was a no-show at this year’s ceremony, resulting in presenter Kieran Culkin making an off-the-cuff joke, or rather a bit of speculative honesty: As an addendum to the standard line that Sean Penn “couldn’t be here tonight,” he added “or didn’t want to be,” nodding to the impression that despite his awards-season popularity, Penn doesn’t always seem so plugged in to the whole campaign scene, especially after so many nominations and wins.
With this third victory, regardless of his gratitude or lack thereof, Penn joins a pretty elite club: He’s only the eighth performer to win at least Academy Awards. Katharine Hepburn currently holds the all-time record with four Best Actress wins. In the three-timers’ club, Penn joins the late Ingrid Bergman and Walter Brennan. The rest of the three-timers are all still with us: Meryl Streep; Jack Nicholson; Daniel Day-Lewis; and Frances McDormand, who joined the list when she won for Normadland five years ago.
Penn’s One Battle After Another nomination for playing rigidly maniacal antagonist Colonel Steven Lockjaw was actually a first for him: It’s the only time he’s ever been Oscar-nominated in the supporting category. All five of his previous nominations were in the leading category; he was in there for Dead Man Walking, Sweet and Lowdown, and I Am Sam. His three wins have also been for his three most recent nominations, suggesting he’s only gotten more popular with his peers as he’s gotten older and more ornery.
While it’s kind of hilarious to see the Academy falling over themselves to re-reward a guy who seems so uninterested in this business that he gave one of his previous Oscars to Ukraine president Volodymyr Zelensky, it’s also kind of heartening to see how these things can’t always be swung with intense campaigning. Sometimes actors can win big without showing up at all, as long as they were bringing it on set.
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