“Sean Penn couldn’t be here tonight—or didn’t want to,” said Kieran Culkin as he accepted the Oscar for Best Supporting Actor on behalf of the acclaimed actor. This moment marked a significant milestone in Penn’s career, as he secured his third Academy Award for his role as Colonel Steven J Lockjaw in the film One Battle After Another.
Penn’s victory at the 98th Academy Awards on March 16, 2026, solidifies his status as one of the most celebrated actors in Hollywood, now holding three Oscars. He previously won Best Actor for Mystic River in 2004 and Milk in 2009, showcasing his versatility and depth as an actor.
His portrayal of Colonel Lockjaw, the film’s essential villain, was met with rave reviews and significant Oscar buzz following the film’s premiere in September. The competition was fierce, with nominees including Jacob Elordi, Delroy Lindo, Stellan Skarsgård, and Benicio del Toro, but Penn’s performance was widely regarded as the standout.
As the awards season progressed, many industry insiders noted, “It felt increasingly like a two-horse race based on the buzz alone,” indicating that Penn’s win was anticipated. The excitement surrounding One Battle After Another was palpable, with 13 nominations in total, further underscoring its impact.
“Penn fully deserves his third statue, and it could be a sign of things to come for One Battle After Another in the major categories as the night progresses,” remarked an observer during the ceremony. This sentiment was echoed by many who believed that Penn’s win was all but guaranteed, with the only question being whether he or del Toro would take home the award.
Despite his absence from the ceremony, Penn’s achievement is a testament to his enduring talent and dedication to his craft. His career, which began with his iconic role as Jeff Spicoli in Fast Times at Ridgemont High in 1982, has now reached new heights with this latest accolade.
Penn’s win not only adds to his impressive list of accomplishments but also reinforces his position as the seventh person in history to win three acting Oscars. As the film industry looks ahead, the anticipation for future projects featuring Penn remains high.
