by Natasha JokicBuzzFeedBuzzFeed StaffI'm a Senior Staff Writer at BuzzFeed covering pop culture, entertainment, and politics. Sean Penn won Best Supporting Actor at the 2026 Oscars, and the response in the room was...mixed. Emma McIntyre / Getty Images It's actually Sean's third Oscar. In 2023, he said of his prior awards, "I thought, well, fuck, you know? I'll give them to Ukraine. They can be melted down to bullets they can shoot at the Russians." CBS Photo Archive / CBS via Getty Images Now, Sean has had a number of controversies and legal troubles over the years.