Trending Now - Sean Penn Wins Third Oscar but Misses 2026 Ceremony

WHO:

Sean Penn, actor and activist

Paul Thomas Anderson, director of "One Battle After Another"

Kieran Culkin, presenter at the 2026 Oscars

President Volodymyr Zelenskyy, President of Ukraine

Other nominees: Stellan Skarsgård, Delroy Lindo, Jacob Elordi, Benicio Del Toro

WHAT:

Sean Penn won the Oscar for Best Supporting Actor for his role as Col. Steven J. Lockjaw in "One Battle After Another"

This win marked Penn's third Oscar, making him the fourth male actor to achieve this milestone

Paul Thomas Anderson's "One Battle After Another" won Best Picture, Best Director, and Best Screenplay at the 2026 Oscars

Kieran Culkin stated, “Sean Penn couldn’t be here this evening — or didn’t want to, so I’ll be accepting the award on his behalf.”

WHERE:

The 2026 Oscars ceremony took place in Los Angeles, California

Sean Penn was reportedly headed to Ukraine

WHEN:

The 2026 Oscars ceremony occurred on March 15th, 2026

Sean Penn had previously won Oscars in 2004 for "Mystic River" and in 2009 for "Milk"

Penn had missed several precursor ceremonies, including the BAFTAs and the Actor Awards in 2026

WHY:

Sean Penn's absence from the Oscars was speculated to be due to his trip to Ukraine, although the exact purpose of his visit was unknown

Penn has expressed a critical view of the Academy, accusing it of “extraordinary cowardice” and limiting cultural expressions

HOW:

Sean Penn had previously suggested that his Oscars could be “melted down to bullets” to support the Ukrainian war effort

Penn had won the Actor Award and the BAFTA for his role in "One Battle After Another" prior to the Oscars

(UPDATED March 16, 2026 19:23 UTC)

At the 2026 Oscars held in Los Angeles on March 15, Sean Penn won the Oscar for Best Supporting Actor for his role as Col. Steven J. Lockjaw in "One Battle After Another," marking his third Oscar and making him the fourth male actor to reach this milestone. Paul Thomas Anderson's film also took home awards for Best Picture, Best Director, and Best Screenplay, while Kieran Culkin accepted Penn's award on his behalf, noting that he was reportedly headed to Ukraine. Penn's absence raised speculation about his trip, especially given his previous critical remarks about the Academy and his suggestion that his Oscars could be “melted down to bullets” to support the Ukrainian war effort.