Actor Sean Penn may have taken the awards-season playbook to a whole new level.
Less than three weeks before Oscar voting closes, a major feature story highlighting the actor’s decade-old humanitarian efforts was published in New York Magazine. The 98th Academy Awards are scheduled to be held on March 15, 2026.
The timing has raised questions, since Penn, who has already won two Oscars, is now competing in a close Supporting Actor race. The article describes the 65-year-old as a determined advocate working behind the scenes.
The story shares an example from 2013, when Penn got involved in the case of Jacob Ostreicher, an American businessman who spent 18 months in a Bolivian prison without being charged.
According to sources, Penn used his connection with Bolivia’s President to help free Ostreicher. Jacob Ostreicher was released in December 2013. The article also referred to Sean Penn as an “ambassadorial thrill seeker.”
Even though the narrative dates back more than a decade, many asked why the publication released it a few days before the voting line closed. For many people, whether they are attending, hosting or taking home the golden statue, it will count as a career-defining moment.
With the race for the Oscars starting early, the most important part of the season is the final voting period, when Academy members choose the winners.
The last round of voting for the 2026 Oscars begins on Feb. 26 at 9 a.m. PT and ends on March 5 at 5 p.m. PT. During these eight days, Academy members vote online using a secret ballot.
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Sean Penn’s campaign for Supporting Actor has been very competitive. He started with the TV series “Little House on the Prairie” in 1974, then moved to films like the 1981 action drama “Taps,” building a strong reputation as an actor.
His recent win as Best Supporting Actor at the 2026 BAFTA Awards for his role as Col. Steven J. Lockjaw in “One Battle After Another” marked another major milestone before the Oscars.
If Sean Penn wins the Academy Award next month, it will be his third Academy Award, following “Mystic River” in 2004 and “Milk” in 2009.
Many people think awards shows are based only on talent, but the reality is more complicated. To be seen as a strong candidate, one needs good PR, public visibility, and active campaigning.
Oscar races have often involved bold and controversial moves to retain the spotlight. For example, in 2011, actress Melissa Leo paid for her own “For Your Consideration” ads in trade magazines while campaigning for her 2008 film “Frozen River.
The strategy worked, and Leo eventually won the awards for Best Supporting Actress.
In an interview, Penn spoke with Newsweek’s Editor-in-Chief Jennifer H. Cunningham at his Malibu home, sharing his thoughts on his life, career, and the creative possibilities of AI.
When asked how Penn would define success and the praise that follows after it, the two-time Oscar winner had a humble reply. He claimed that respect for an actor’s work has more value when he himself is proud of their work and efforts.
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“If someone tells me, ‘You did a great job,’ I almost wish the message came with a note saying, ‘Don’t respond,’” he said. Before Sean Penn won the Oscar for “Mystic River,” he had previously skipped ceremonies even when nominated.
That year, he attended mainly because he felt bad that Clint Eastwood had accepted his Golden Globe on his behalf. “I went and I happened to win, and the only feeling I could ever have winning is relief”.
He also thanked the people who supported his Oscar win, saying, “You’re just relieved they didn’t waste their time.”
He then added a humorous remark: “I probably would have been a lot more excited watching from my couch.”
