“Sean Penn couldn’t be here this evening, or didn’t want to, so I’ll be accepting the award on his behalf,” said Kieran Culkin during the Oscars ceremony, where Penn was notably absent despite winning the Best Supporting Actor award for his role in One Battle After Another.

On March 16, 2026, the day after the Oscars, Penn was photographed in Kyiv, underscoring his commitment to supporting Ukraine amid the ongoing conflict with Russia. His absence from the prestigious event aligns him with a historical lineage of celebrities who have skipped the ceremony for various reasons.

Previously, Penn has been a vocal advocate for Ukraine, lending one of his Oscar statuettes to President Volodymyr Zelensky with the promise that it would remain in Kyiv until Ukraine wins the war. This gesture reflects his deep-rooted activism, which has been influenced by his family’s liberal politics; his father was blacklisted from Hollywood in the 1950s.

Sean Penn, now 65, has a history of political and humanitarian activism, having worked in various conflict zones including Iraq and Haiti. His commitment to social causes has often overshadowed his film career, which includes three Academy Awards, with previous wins for Mystic River in 2004 and Milk in 2009.

The last time a winner skipped the Oscars before Penn was in 2024, marking a rare occurrence in the ceremony’s history. Penn’s absence has sparked conversations about the intersection of celebrity culture and political activism.

As the situation in Ukraine continues to evolve, Penn’s actions and statements are likely to remain in the spotlight. His dedication to the cause has resonated with many, positioning him as a significant figure in the ongoing discourse surrounding the conflict.

Details remain unconfirmed regarding any future statements from Penn or his representatives about his absence at the Oscars. However, his presence in Kyiv suggests that his focus remains on supporting Ukraine during these challenging times.

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Kieran Culkin made a striking appearance at the 2026 Oscars, where he wore a brooch designed by Bertrand Mak. The event, held on March 16, 2026, showcased not only cinematic achievements but also remarkable fashion statements from attendees.

The brooch, which features a singular brushstroke from an internationally acclaimed contemporary Asian artist, was highlighted for its intricate design. Bertrand Mak described the piece, stating, “It’s a singular brushstroke from the work of an internationally acclaimed contemporary Asian artist.” The craftsmanship included hand engraving and guilloché finishing by the Voutilainen atelier, underscoring the artistic value of the accessory.

During the ceremony, Kieran Culkin humorously ribbed fellow actor Sean Penn, who won the Best Supporting Actor Oscar for his role in “One Battle After Another.” Culkin remarked, “Sean Penn couldn’t be here this evening — or didn’t want to,” drawing laughter from the audience. This comment not only highlighted the camaraderie among actors but also Penn’s notable absence from the prestigious event.

Sean Penn’s win marked his third Oscar, making him only the fourth male actor to achieve this milestone. His previous Oscar victories were for “Mystic River” in 2003 and “Milk” in 2008. The recognition of his talent continues to resonate within the film industry, as he joins the ranks of legendary actors like Katharine Hepburn, who holds the record with four acting Oscars.

The Oscars have evolved into a significant fashion event in recent years, with attendees often using the platform to showcase unique styles and artistic expressions. Kieran Culkin’s choice of the brooch reflects this trend, merging fashion with artistry and personal expression.

As the evening unfolded, Conan O’Brien, who hosted the event, added to the excitement by teasing the audience with his signature humor, saying, “This thing’s a humdinger — you gotta stay tuned!” His remarks kept the atmosphere lively and engaging, further enhancing the overall experience of the night.

Reactions to the event have been varied, with many praising Culkin’s fashion choice and playful banter. The blend of humor and high fashion at the Oscars continues to captivate audiences and spark discussions about the intersection of cinema and style. Details remain unconfirmed regarding future collaborations between Culkin and Mak, but the evening undoubtedly left a lasting impression on attendees and viewers alike.

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“Sean Penn couldn’t be here tonight—or didn’t want to,” said Kieran Culkin as he accepted the Oscar for Best Supporting Actor on behalf of the acclaimed actor. This moment marked a significant milestone in Penn’s career, as he secured his third Academy Award for his role as Colonel Steven J Lockjaw in the film One Battle After Another.

Penn’s victory at the 98th Academy Awards on March 16, 2026, solidifies his status as one of the most celebrated actors in Hollywood, now holding three Oscars. He previously won Best Actor for Mystic River in 2004 and Milk in 2009, showcasing his versatility and depth as an actor.

His portrayal of Colonel Lockjaw, the film’s essential villain, was met with rave reviews and significant Oscar buzz following the film’s premiere in September. The competition was fierce, with nominees including Jacob Elordi, Delroy Lindo, Stellan Skarsgård, and Benicio del Toro, but Penn’s performance was widely regarded as the standout.

As the awards season progressed, many industry insiders noted, “It felt increasingly like a two-horse race based on the buzz alone,” indicating that Penn’s win was anticipated. The excitement surrounding One Battle After Another was palpable, with 13 nominations in total, further underscoring its impact.

“Penn fully deserves his third statue, and it could be a sign of things to come for One Battle After Another in the major categories as the night progresses,” remarked an observer during the ceremony. This sentiment was echoed by many who believed that Penn’s win was all but guaranteed, with the only question being whether he or del Toro would take home the award.

Despite his absence from the ceremony, Penn’s achievement is a testament to his enduring talent and dedication to his craft. His career, which began with his iconic role as Jeff Spicoli in Fast Times at Ridgemont High in 1982, has now reached new heights with this latest accolade.

Penn’s win not only adds to his impressive list of accomplishments but also reinforces his position as the seventh person in history to win three acting Oscars. As the film industry looks ahead, the anticipation for future projects featuring Penn remains high.

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