Oscars 2026: Sean Penn Wins Oscar for Best Actor in a Supporting Role

The Oscars were swinging right along. Sean Penn won the 2026 Academy Award for Best Actor in a Supporting Role. The nominees were Benicio Del Toro, for the same movie; Delroy Lindo; Jacob Elordi; and Stellan Skarsgard.

Penn, born in 1960, has now won three Oscars. He is decorated with a Golden Globe Award, a British Academy Film Award, and nominations for Emmy and Grammy Awards. He received the Honorary César in 2015 and the Bob Hope Humanitarian Award in 2022. How many more Oscars do you think Sean Penn will win?

Best Actor in a Supporting Role

Sean Penn won the Oscar for Best Actor in a Supporting Role for his performance in the movie “One Battle After Another.” The film follows Bob Ferguson, who is played by Leonardo DiCaprio. He is a former revolutionary who has retired from radical life. Years later, he is brought out of hiding when he and his daughter, Willa Ferguson, played by Chase Infiniti, are hunted by the deranged Colonel Steven J. Lockjaw, played by Sean Penn.

“One Battle After Another” also stars Benicio Del Toro. He was nominated for best supporting actor as well. There was some thought that having two Oscar Best Supporting Actor Nominees from the same movie would hurt them both; it clearly did not in this case. The film was critically acclaimed, although it is a strange dystopian drama.

More on Sean Penn

Sean Penn, who won the Oscar in 2026 for best supporting actor, did not attend the Academy Awards this year. The Award presenter accepted the award for him and joked that maybe he chose to miss the Academy Awards this year.

Penn debuted in “Taps” in 1981; he was in “Fast Times at Ridgemont High” in 1982, “Bad Boys” in 1983, and “At Close Range” in 1986. He has won three Academy Awards, or Oscars, Best Actor twice for playing a grieving father in “Mystic River” in 2003 and the gay rights activist Harvey Milk, in “Milk” in 2008. He was also Oscar-nominated for “Dead Man Walking” in 1995, “Sweet and Lowdown” in 1999, and “I Am Sam” in 2001. He has also been in more than ten additional movies.

Parting Shots

It is a little strange that Sean Penn did not attend the Oscars this year. Maybe he did not think he was going to win. Well, he did. Maybe he thought having two nominees from the same movie would decrease the chances for both nominations. Or, maybe he is protesting something.