Sean Penn’s Oscars Journey: From Gift to Zelenskyy to Skipping the Ceremony

Sean Penn’s relationship with the Academy Awards has taken a complex turn in recent years, marked by both recognition and a growing distance from the traditional Hollywood celebration. The two-time Oscar winner, nominated for Best Supporting Actor for his role in “One Battle After Another” at the 2026 ceremony, has been notably absent from awards shows, a pattern that began after gifting one of his statuettes to Ukrainian President Volodymyr Zelenskyy in 2022.

The Gift to Zelenskyy: A Symbol of Support

In the wake of Russia’s invasion of Ukraine, Penn traveled to the war-torn country and forged a close connection with President Zelenskyy. As a demonstration of solidarity, Penn gifted Zelenskyy an Oscar award. According to The Hollywood Reporter, the Oscar presented was the one he received for his performance in the 2003 film “Mystic River.” Penn reportedly told Zelenskyy to return the award “when you win.”

Zelenskyy acknowledged the gesture, stating it provided a sense of strength during a difficult time. Penn also received Ukraine’s Order of Merit in the third degree during his visit, recognizing his outspoken advocacy and support.

A Complicated Relationship with the Oscars

Prior to the gift, Penn had a fraught relationship with the Academy. In 2022, he threatened to melt his Oscars if the Academy did not allow Zelenskyy to address the ceremony, a request that was ultimately denied. Despite being nominated for “One Battle After Another,” Penn continued to skip the 2026 Oscars, following a pattern of absence from the BAFTAs and Actor Awards as well.

Looking Ahead

Penn, who last enjoyed the process of acting during the filming of “Milk” eighteen years ago, has expressed a renewed interest in the craft due to his involvement in “One Battle After Another.” However, he remains focused on directing and finding projects that resonate with the current global landscape. He also has a film planned with Tom Hardy, but stated he is not actively seeking new roles, preferring to wait for opportunities that genuinely inspire him.