‘One Battle After Another’ Sean Penn, Oscar Best Supporting Actor… Achieves '4th in History' with 3 Wins

Won Best Supporting Actor for the film ‘One Battle After Another’… Standing shoulder to shoulder with Daniel Day-Lewis and Jack Nicholson Perfectly transformed into the persona of director Paul Thomas Anderson… A bizarre and intense performance as ‘Colonel Stephen Lockzo’ Kieran Culkin accepted the award on his behalf, stating, “Overwhelming acting that made Oscar disdain seem trivial”

On March 15, 2026, at the 98th Academy Awards held at the Dolby Theatre in Hollywood, California, the American actor Sean Penn is captured on stage after winning the Best Supporting Actor award for the film 《One Battle After Another》. (Photo by Patrick T. Fallon / AFP)
On March 15, 2026, at the 98th Academy Awards held at the Dolby Theatre in Hollywood, California, the American actor Sean Penn is captured on stage after winning the Best Supporting Actor award for the film 《One Battle After Another》. (Photo by Patrick T. Fallon / AFP)

Hollywood's 'acting master' Sean Penn has embraced his third Oscar trophy, joining the ranks of legendary actors. On the 15th (local time) at the 98th Academy Awards held in Los Angeles, Sean Penn won the Best Supporting Actor award for the film ‘One Battle After Another’.

◆ A historic record of 3 wins… Sean Penn rewrites Hollywood history

With this award, Sean Penn joins the elite group of actors who have won Oscar acting awards three times or more, including Daniel Day-Lewis, Jack Nicholson, and Walter Brennan. Penn previously won Best Actor twice for ‘Mystic River’ in 2004 and ‘Milk’ in 2009. He received the honor of winning this award, beating out strong contenders including Benicio Del Toro from the same film, Delroy Lindo (The Harder They Fall), and Stellan Skarsgård (The King's Man).

◆ A groundbreaking character as ‘Colonel Stephen Lockzo’

In ‘One Battle After Another’, directed and written by Paul Thomas Anderson (PTA), Sean Penn delivered a groundbreaking performance as military officer Colonel Stephen J. Lockzo. In the film, he perfectly embodied a complex and bizarre character who feels sexual shame while simultaneously becoming obsessed with the character played by Teyana Taylor. Local critics praised, “Sean Penn's unique sharp charisma combined with PTA's experimental direction created the best performance of the year.”

On March 15, 2026, at the 98th Academy Awards held in Hollywood, Los Angeles, USA, Benicio Del Toro applauds as Sean Penn wins the Best Supporting Actor award for the film 《One Battle after Another》. REUTERS/Mike Blake
On March 15, 2026, at the 98th Academy Awards held in Hollywood, Los Angeles, USA, Benicio Del Toro applauds as Sean Penn wins the Best Supporting Actor award for the film 《One Battle after Another》. REUTERS/Mike Blake

◆ The return of the ‘Oscar skeptic’… Overwhelming support despite absence from the ceremony

Sean Penn, who has shown a cynical attitude towards the Academy Awards, did not appear at the ceremony. His acceptance speech was delivered by actor Kieran Culkin, who served as the presenter. Despite his absence from the ceremony, Penn has been considered a strong Oscar contender early on, sweeping the Best Supporting Actor awards at the British Academy (BAFTA) and the Screen Actors Guild (SAG) this year.

◆ Ensemble with Leonardo DiCaprio… Captured both box office and critical acclaim

This film, which features Leonardo DiCaprio as a former revolutionary, has been described as a bizarre crime drama dealing with counterculture. Despite being a supporting role, Sean Penn showcased a presence that overshadowed the lead, marking another peak in his acting career. Even in his 70s, he continues to display energy comparable to his prime, earning praise from film fans worldwide.

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