Sean Penn has made history, becoming only the second actor – alongside Daniel Day-Lewis – to win three Academy Awards. He first took home the prize in 2004 for Mystic River, then again in 2009 for Milk, and most recently for his powerful performance as the film’s villain in “One Battle After Another.”
The Paul Thomas Anderson-directed film clocks in at 161 minutes, but despite appearing on screen for just 30 minutes, Penn’s performance was enough to secure him the Best Supporting Actor award. The win comes as “One Battle After Another” continues to garner critical acclaim – our critic called it the film of the year – and boasts a stellar ensemble cast. Penn beat out fellow nominees Benicio Del Toro, also from “One Battle After Another,” Jacob Elordi for “Frankenstein,” Delroy Lindo for “Sinners,” and Stellan Skarsgård for “Sentimental Value.”
Despite the success of “One Battle After Another,” which received 13 nominations, Penn was not present at the awards ceremony. According to reports, the actor has opted to travel to Europe, with plans to visit Ukraine, continuing his vocal support for Ukrainian President Volodymyr Zelensky, to whom he previously gifted one of his Oscars in 2022. The actor reportedly didn’t campaign heavily for the award, letting his work speak for itself – a strategy that some believe more nominees should adopt.
The other nominees for the 2026 Oscar for Best Supporting Actor
Previous Oscar winners for Best Supporting Actor
- 2025 – Kieran Culkin for ‘A Real Pain’
- 2024 – Robert Downey Jr. For ‘Oppenheimer’
- 2023 – Ke Huy Quan for ‘Everything Everywhere All at Once’
- 2022 – Troy Kotsur for ‘CODA’
- 2021 – Daniel Kaluuya for ‘Judas and the Black Messiah’
- 2020 – Brad Pitt for ‘Once Upon a Time in… Hollywood’
- 2019 – Mahershala Ali for ‘Green Book’
- 2018 – Sam Rockwell for ‘Three Billboards Outside Ebbing, Missouri’
- 2017 – Mahershala Ali for ‘Moonlight’
- 2016 – Mark Rylance for ‘Bridge of Spies’
- 2015 – J.K. Simmons for ‘Whiplash’
- 2014 – Jared Leto for ‘Dallas Buyers Club’
- 2013 – Christoph Waltz for ‘Django Unchained’
- 2012 – Christopher Plummer for ‘Beginners’
- 2011 – Christian Bale for ‘The Fighter’
- 2010 – Christoph Waltz for ‘Inglourious Basterds’
- 2009 – Heath Ledger for ‘The Dark Knight’
- 2008 – Javier Bardem for ‘No Country for Aged Men’
- 2007 – Alan Arkin for ‘Little Miss Sunshine’
- 2006 – George Clooney for ‘Syriana’
- 2005 – Morgan Freeman for ‘Million Dollar Baby’
- 2004 – Tim Robbins for ‘Mystic River’
- 2003 – Chris Cooper for ‘Adaptation’
- 2002 – Jim Broadbent for ‘Iris’
- 2001 – Benicio del Toro for ‘Traffic’
- 2000 – Michael Caine for ‘The Cider House Rules’
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