Paul Thomas Anderson’s Long-Awaited Oscar Night Comes With a Bonus: Sean Penn’s Third Win

Paul Thomas Anderson has made films that critics have called masterpieces. He has been nominated, discussed, and admired for decades. But on Sunday night at the 98th Academy Awards, he finally won — twice. One Battle After Another earned Anderson both Best Adapted Screenplay and Best Director, completing a chapter in awards history that many felt was long overdue. The same film also handed Sean Penn his third Oscar for Best Supporting Actor, tying the all-time male acting record. The one note of strangeness was that Penn wasn’t there.
Presenter Kieran Culkin collected Penn’s award and offered a dry explanation for the actor’s absence, getting a knowing laugh from the crowd. Penn’s three wins now match those of Jack Nicholson, Walter Brennan, and Daniel Day-Lewis — the only men to previously reach that total. His prior victories were for Best Actor in Mystic River and Milk, performances that have become benchmarks of their respective eras.
Penn’s role in One Battle After Another — a militaristic officer controlled by his own extremism — was called by critics one of the most intense and disciplined performances of the year. Anderson’s direction shaped that intensity into something both dark and funny, and the Academy rewarded the result accordingly. For Anderson, the double win was the culmination of a career defined by creative courage and uncompromising vision.
Host Conan O’Brien was sharp and warm, using his opening monologue to address both the humor and the anxiety of the present moment. He joked about artificial intelligence threatening his own role as host and celebrated the diversity of the nominees, who came from 31 countries on six continents. His hosting was widely praised as one of the better recent Oscar performances in that role.
Michael B. Jordan claimed Best Actor for Sinners over Leonardo DiCaprio, adding one more memorable result to a memorable night. The 2026 Oscars were a landmark evening for Anderson, Penn, and Jordan — though Penn, as usual, wasn’t around to hear the applause.