Oscars 2026: ‘One Battle After Another’ Star Sean Penn Becomes Fourth Male Actor To Win 3 Academy Awards, Who Are the Other Winners?

Sean Penn made history at the 98th Academy Awards on Sunday night, becoming only the fourth male actor to earn three competitive acting Oscars. Penn took home the trophy for Best Supporting Actor for his performance in Paul Thomas Anderson’s political drama, One Battle After Another. Oscars 2026: Sean Penn Wins Best Supporting Actor for ‘One Battle After Another,’ Joins Elite Three-Win Club Despite Skipping Ceremony.

The win solidifies Penn’s status as a titan of modern cinema, moving him into an exclusive tier of performers that has remained unchanged for over a decade. Despite the historic nature of the achievement, Penn was notably absent from the ceremony at the Dolby Theatre, with presenter Kieran Culkin accepting the award on his behalf.

Sean Penn Pen Wins Best Supporting Actor for ‘One Battle After Another’ at Oscars 2026

In One Battle After Another, Penn portrays Colonel Steven J Lockjaw, a complex and morally ambiguous military figure. Critics have praised the performance for its "volatile intensity" and "commanding presence," marking a stark contrast to the leading roles that earned him his previous accolades.

Penn’s victory on Sunday followed a successful sweep of the precursor awards, including wins at the BAFTAs and the Screen Actors Guild (SAG) Awards. His win on Oscar night came against a formidable field of nominees, including Stellan Skarsgard (Sentimental Value) and Delroy Lindo (Sinners).

Sean Penn Wins Best Supporting Actor for ‘One Battle After Another’ at Oscars 2026

The Four-Man Club of Three-Time Oscar Winners

With this third statuette, Penn joins a shortlist of male actors who have achieved a trio of acting wins. Before Sunday, only three men in the history of the Academy had reached this milestone:

Walter Brennan is the first to achieve the feat. Brennan won three Best Supporting Actor awards for Come and Get It (1936), Kentucky (1938), and The Westerner (1940).

Jack Nicholson, who is one of the most nominated actors in history, won for One Flew Over the Cuckoo's Nest (1975, Lead), Terms of Endearment (1983, Supporting), and As Good as It Gets (1997, Lead).

The legendary Daniel Day-Lewis is the only man to win three awards in the Best Actor (Lead) category. He was honoured for My Left Foot (1989), There Will Be Blood (2007), and Lincoln (2012).

Penn’s previous wins were both in the Lead Actor category, for his haunting performance in the crime drama Mystic River (2003) and his portrayal of activist Harvey Milk in Milk (2008).

Highlights from the 2026 Oscars

The 98th Academy Awards, hosted by Conan O’Brien, were a night of significant milestones beyond Penn’s historic win. Paul Thomas Anderson’s One Battle After Another emerged as one of the evening's big winners, taking home the top prize for Best Picture. Oscars 2026 Winners List: ‘One Battle After Another’ Wins Best Picture; Michael B Jordan and Jessie Buckley Win Top Acting Awards.

Other notable winners included Michael B Jordan, who secured his first Oscar for his lead role in the thriller Sinners, and Amy Madigan, who won Best Supporting Actress for Weapons. The ceremony also made history in technical categories, with Sinners cinematographer Autumn Durald Arkapaw becoming the first woman to win in that category.

(The above story first appeared on LatestLY on Mar 16, 2026 12:24 PM IST. For more news and updates on politics, world, sports, entertainment and lifestyle, log on to our website latestly.com).