Sean Penn Wins Third Acting Oscar, Accepts Award While in Ukraine

Sean Penn was awarded his third career acting Oscar at the 98th Academy Awards for his performance in "One Battle After Another," marking a significant career milestone. Penn did not attend the ceremony in Los Angeles, having traveled to Ukraine where he met with President Volodymyr Zelenskyy. Kieran Culkin accepted the award on Penn's behalf.

A Historic Third Acting Oscar

Sean Penn received the Best Supporting Actor award for his portrayal of Colonel Steven J Lockjaw in the film "One Battle After Another," directed by Paul Thomas Anderson and co-starring Leonardo DiCaprio.

This marks Penn's first Oscar for a supporting role; his previous two Academy Awards were for Best Actor in "Mystic River" (2004) and "Milk" (2009).

With this third acting Oscar, Penn joins Daniel Day-Lewis, Jack Nicholson, and Walter Brennan as male actors who have achieved three acting Oscars. The film "One Battle After Another" secured a total of six awards at the ceremony, including Best Director and Best Picture.

Earlier in the awards season, Penn had also won Best Supporting Actor for this role at the BAFTA Awards and the Actor Awards. He received nominations at the Golden Globes and Critics Choice awards; those awards went to Stellan Skarsgard and Jacob Elordi, respectively.

Ukraine Engagement Takes Precedence Over Ceremony

Penn was not present at the 98th Academy Awards ceremony at the Dolby Theatre in Los Angeles on Sunday night. Kieran Culkin, who had won the supporting actor award the previous year, accepted the award on Penn's behalf, remarking, "Sean Penn couldn't be here this evening—or didn’t want to." Penn had also been absent from the Actor Award and BAFTA award ceremonies where he had won for the same role.

Reports indicated that Penn traveled to Ukraine instead of attending the Oscars, meeting with Ukrainian President Volodymyr Zelenskyy in Kyiv. President Zelenskyy later posted a picture of himself with Penn on X.

President Zelenskyy expressed gratitude for Penn's "sustained support of Ukraine since the initial day of the full-scale war."

Penn's visit is part of his ongoing involvement in Ukraine following the 2022 Russian invasion. In 2022, Penn had loaned one of his previous Oscar statues to President Zelenskyy, stating it was a "symbol of faith" and that he would "feel better and stronger for the fight" knowing it was with him, requesting its return upon Ukraine's victory. Penn has visited Ukraine frequently and produced the 2023 documentary "Superpower," which chronicles his encounters with President Zelenskyy.

During his recent visit, Penn also received a custom "Oscar" statue made from the metal of a Ukrainian railway carriage damaged by Russian missiles. Oleksandr Pertsovskyi, CEO of Ukrainian railways, presented the flat, silver, Academy Award-shaped statue to Penn, stating, "You’re missing Oscars, so we made this one. It’s not golden but it’s very real and from the bottom of our hearts." Penn accepted the gift, referring to them as "treasures."

A History of Political Statements and Awards Criticism

Penn has a history of using previous Oscar wins as platforms to address political issues, such as the Iraq War in 2004 and LGBTQ+ rights in 2009.

He has also previously expressed criticism of the Academy Awards, referring to them as "extraordinary cowardice" in 2024 for limiting cultural expressions and stating a lack of excitement for the event.

Other nominees in the Best Supporting Actor category included:

• Benicio del Toro for "One Battle After Another"
• Delroy Lindo for "Sinners"
• Stellan Skarsgård for "Sentimental Value"

Benicio del Toro had received multiple critics' awards prior to the Oscars.