Sean Penn claimed yet another Academy Award on March 15, winning Best Supporting Actor for his role in Paul Thomas Anderson's 2025 political drama 'One Battle After Another.' The 65-year-old delivered a powerful performance as a seasoned political operative caught in the film's web of shifting allegiances and ideological conflict. However, Penn was absent from the ceremony. "He couldn't be here tonight, or he didn't want to," Kieran Culkin, last year's winner, announced after revealing Penn as the winner.
Penn's decision to skip the Oscars is consistent with his pattern of no-shows. He previously missed three nominations ceremonies—for 'Dead Man Walking' (1996), 'Sweet and Lowdown' (2000), and 'I Am Sam' (2002). The acclaimed actor has also opted out of attending the BAFTAs and Actor Awards this year.
Penn's relationship with the Academy has been marked by notable moments beyond awards wins. In 2022, he donated one of his Oscar statuettes to Ukrainian President Volodymyr Zelenskyy in a show of solidarity.
Indeed, Sean Penn is one of Hollywood's most accomplished actors and filmmakers. He's also one of Tinseltown's most controversial figures. The now three-time Academy Award winner has been applauded for pictures such as 'Mystic River' (2003), 'Milk' (2008), and, now, 'One Battle After Another' (2025). But the star has faced criticism from various quarters for his political activism, although he has also been praised for his humanitarian work.
In this gallery, take a look back at how Hollywood's bad boy made good. Click on for more.