Photo by Harald Krichel / Wikimedia Commons (CC BY-SA 3.0)
16
The next time a male actor wins three Oscars, it will not be for the first time or even the fourth. But it will be rare. Sean Penn claimed his third at the 98th Academy Awards for Best Supporting Actor in One Battle After Another, joining Jack Nicholson, Walter Brennan, and Daniel Day-Lewis in the record books. Penn was not present at the Dolby Theatre to accept the award, and presenter Kieran Culkin stepped in with characteristic dry humor to collect it on his behalf.
Penn’s three wins span Best Actor twice — for Mystic River in 2004 and Milk in 2009 — and now Best Supporting Actor. Each win came for a different kind of role, in a different genre, at a different stage of his career. That breadth of achievement is what makes Penn’s record particularly extraordinary even among its elite company.
His role in One Battle After Another — a military officer whose convictions become a form of self-destruction — drew lavish critical praise throughout the awards season. Paul Thomas Anderson’s direction of the film was equally celebrated, earning him both Best Adapted Screenplay and Best Director — his first career Oscars. Anderson’s double win was among the most applauded moments of the evening and closed a long chapter in the story of his recognition by the Academy.
Host Conan O’Brien was an entertaining and thoughtful presence throughout the ceremony. He opened with a joke about AI making human entertainers obsolete and celebrated the diversity of the nominees, drawn from 31 countries on six continents. His performance as host was praised as one of the more accomplished in recent Oscar history.
Michael B. Jordan’s Best Actor win for Sinners over Leonardo DiCaprio was one of the evening’s biggest surprises. For Penn, the question is not whether another man will match his record — it is whether anyone will match the particular strangeness and brilliance with which he achieved it.
