Penn, Anderson, and Jordan Dominate a Historic Night at the 2026 Academy Awards

Three men shaped the 98th Academy Awards more than any others: Sean Penn, Paul Thomas Anderson, and Michael B. Jordan. Penn won his record-tying third Oscar for Best Supporting Actor in One Battle After Another. Anderson won his long-awaited first Oscars — for Best Adapted Screenplay and Best Director — for the same film. And Jordan won Best Actor for Sinners, defeating Leonardo DiCaprio. The evening was one for the history books.
Penn’s absence from the ceremony was both a surprise and, for those who know him, entirely predictable. Presenter Kieran Culkin accepted the Best Supporting Actor award on Penn’s behalf and noted, with characteristic dryness, that Penn either couldn’t or didn’t want to be there. Penn’s three wins now match those of Jack Nicholson, Walter Brennan, and Daniel Day-Lewis — all of whom did show up for their victories.
In One Battle After Another, Penn plays a military officer undone by extremism — a role critics described as one of the most demanding and rewarding of his career. Anderson’s film was one of the season’s most discussed, and the director’s double win capped years of close-but-no-prize finishes at the Academy Awards. His first Oscars came in a year when he also produced one of Penn’s finest screen performances.
Conan O’Brien was a skilled and warm host, opening with a monologue that addressed both AI-driven anxieties and the global scope of modern cinema. He noted that nominees came from 31 countries across six continents — a record that reflects the Academy’s ongoing expansion beyond its Hollywood roots. His performance was regarded as one of the better recent Oscar hosting efforts.
Michael B. Jordan’s Best Actor victory for Sinners over DiCaprio closed a night that was full of memorable firsts, lasts, and records. The 2026 Oscars were, quite simply, a landmark evening in the ceremony’s long and storied history.