Sean Penn’s Third Oscar Win Comes With No Podium, No Speech, No Penn

The 2026 Academy Awards produced one of their most memorable and eccentric moments when Sean Penn became a three-time Oscar winner while simultaneously being absent from the building where that honor was bestowed. Penn won Best Supporting Actor for his role in Paul Thomas Anderson’s One Battle After Another, but the podium stayed empty until Kieran Culkin stepped forward to accept on his behalf. Culkin’s joke about Penn’s non-attendance broke the tension and brought the audience together.
Penn’s three wins tie him with Jack Nicholson, Walter Brennan, and Daniel Day-Lewis — the only male actors in Academy Awards history to have won three acting Oscars. Having previously claimed Best Actor for Mystic River in 2004 and Milk in 2009, Penn now spans both major acting categories in his wins. His legacy as one of the most awarded and most respected actors of his era is now firmly written into the record books.
In One Battle After Another, Penn plays an obsessive military officer who becomes consumed by his own beliefs — a role that critics called among the finest of his career. Director Paul Thomas Anderson celebrated alongside the film’s accolades, winning Best Director and Best Adapted Screenplay in a landmark night for his filmmaking career. Both wins were his first, coming after decades of critically acclaimed but previously unrecognized work.
Host Conan O’Brien opened the evening with a knowing joke about artificial intelligence displacing entertainers, a concern that has real traction in the film industry. He also struck a global note, highlighting the diversity of nominees from 31 countries on six continents. O’Brien’s hosting was praised as both entertaining and emotionally intelligent.
Michael B. Jordan beat Leonardo DiCaprio to the Best Actor prize for his remarkable performance in Sinners. The 2026 Oscars served up history, humor, and a very notable empty chair — all the ingredients for a ceremony that will be talked about for years.