Sean Penn achieved a personal milestone at the 98th Academy Awards, winning his third Oscar for his role in One Battle After Another. His absence was felt at the ceremony when he failed to collect it. Thus, building a sense of intrigue on why he decided to skip the prestigious award show.
According to the reports from The New York Times, the Mystic River actor decided to skip attending the Oscars and head to Ukraine. Two anonymous sources came forward and stated that Penn had planned the visit to the European country last week. But they refrained from sharing his specific plans on what he was doing there.
Is there a reason why Sean Penn wasn’t there? Because that was a bit of an awkward statement and look from Kieran, no? #Oscar
— double foot amputee colonel sanders (@thisisnefertiti) March 16, 2026
Since his plans were not mentioned, it remains unclear what he is doing there. However, he has spent significant time in Ukraine since 2022. In fact, he made a documentary titled Superpower, showcasing Vladimir Putin’s Russia launching a military invasion of the country.
During an interview with Variety, he expressed his anger over the Academy Awards refusing to let Volodymyr Zelenskyy speak during the 2022 ceremony. The three-time Oscar winner was fuming to the point of destroying one of his awards to make a bullet out of it. Penn said,
“I thought, well, f***, you know? I’ll give them to Ukraine. They can be melted down to bullets they can shoot at the Russians.”
Additionally, the Bad Boys actor was not a huge fan of attending the ceremony because it was not “light-hearted enough.” And then referred to Will Smith’s infamous moment with Chris Rock. Again in 2024, during an interview with Variety, he slammed the institution for its exhibition of “extraordinary cowardice.”
Sean Penn’s reaction to winning his third Oscar.
“……………………..” pic.twitter.com/N5AFiVToQm
— DiscussingFilm (@DiscussingFilm) March 16, 2026
He added that this trait was largely responsible for not only limiting the imagination but also limiting different cultural expressions. As a result, it is segregated from becoming a “part of the bigger world of expression.” He called the Oscars a TV show rather than a scale to determine an artist’s merit.
If we connect the dots, Penn’s lack of enthusiasm to attend the ceremony makes sense. After all, it was his sixth nomination and a third win for the Best Supporting Actor category. While the veteran actor was least interested in attending the ceremony, Kieran Culkin, the presenter of the category, joked,
“Sean Penn couldn’t be here this evening, or didn’t want to, so I’ll be accepting the award on his behalf.”
Though he prefers to spend his time in Ukraine, this win makes him an exclusive member of a limited club of actors who have won the Oscars three times.
