Walter Brennan Would Understand: Sean Penn’s Third Oscar Is Pure Old Hollywood Spirit in a New Package

Walter Brennan was the first man to win three acting Oscars. Jack Nicholson did it decades later, followed by Daniel Day-Lewis. And on Sunday night at the 98th Academy Awards, Sean Penn became the fourth. Penn won Best Supporting Actor for One Battle After Another without attending the ceremony — a detail that Brennan, who was famously forthright about his opinions of Hollywood politics, might have appreciated. Presenter Kieran Culkin collected the award with characteristic dry wit.

Penn’s three Oscars span a career defined by intensity, selectivity, and an almost willful avoidance of the industry’s social machinery. His wins for Mystic River and Milk were both recognized at the time as among the finest acting performances in recent Oscar history. This third win, for a supporting role in a Paul Thomas Anderson film, places a definitive capstone on a career that has always been about the work.

One Battle After Another gave Penn one of his most complex and demanding roles — a militaristic officer whose internal certainties become outward catastrophes. Paul Thomas Anderson’s direction turned that performance into a landmark film, and Anderson was rewarded with his first two Oscars for Best Adapted Screenplay and Best Director. The wins drew one of the longest standing ovations of the evening.

Host Conan O’Brien struck a thoughtful balance between humor and cultural commentary. He opened with a joke about artificial intelligence making human hosts obsolete before pivoting to a sincere celebration of cinema’s global relevance. He highlighted the record 31 countries represented among the nominees, calling the ceremony a gathering of the world’s finest filmmakers and performers.

Michael B. Jordan claimed Best Actor for Sinners, defeating Leonardo DiCaprio in one of the evening’s closest and most anticipated contests. The 2026 Oscars added to a century-long history with a night worthy of the occasion.