Sean Penn explained his much-discussed absence from the Academy Awards in March, where he missed out on accepting his third Oscar in person, while appearing at the Tribeca Festival in New York on Friday for a Storytellers series moderated by CNN’s Kaitlan Collins.
The intense, supremely talented, and at times mercurial actor and global activist was at the festival a year late, after having to cancel his planned 2025 slot because of a death in his family. On Friday evening, he sat with Collins, who hosts The Source with Kaitlan Collins weeknights on the cable news channel while also serving as the network’s Chief White House Correspondent.
Penn won his third Oscar in March for best supporting actor for his role as repressed oppressor Col. Steven J. Lockjaw in Paul Thomas Anderson’s lauded Best Picture winner One Battle After Another. This added to his best actor wins for Mystic River in 2004 and Milk in 2009. Penn was notably absent from the Oscars ceremony to accept the award he was tipped to win; days later, it was revealed that he had flown to Ukraine to meet with Volodymyr Zelenskyy. After agreeing he should not attend the awards with his One Battle After Another team, he said he deliberately timed his Ukraine trip to coincide with the Oscars telecast.
“The best that I could ever muster was relief,” he admitted. “Knowing that I wasn’t going to do that anymore, I did one before that this year. I went to the Golden Globes; I’d never been to that before. And that’s where I decided, ‘I can’t do this.’”
“[The Oscars] always represented social discomfort to me,” he added.
Penn explained a rule about social gatherings to the reporter and the packed crowd at Spring Studios in lower Manhattan. “I won’t go anywhere to be with a designated group beyond eight people. If you cut out two hours for your night, it gives you 15 minutes per person.”
But don’t add a ninth person, Penn said, as a larger-than-eight crowd is “just anxiety- and dread-inducing.” Despite this — or perhaps because of it — Penn said he has managed to “mellow out” over the years, shedding the reputation for punching photographers and attacking castmates with screaming matches and other well-publicized anti-social behavior that his youthful antics had handed to the revered actor.
Not that he’s 100 percent approachable these days. Penn told the crowd that the act of taking a selfie, even with some of his biggest fans, no matter their walk of life, is not going to happen — ever.
“People should not do selfies ever with anyone. It’s bad for you; it’s bad for everyone. It’s a soul-sucker,” he said, garnering a big laugh from the packed house as the audience hung on his every word. “It’s the Holocaust grandmother and her 6-year-old paraplegic wheeling over? It’s a hard no.”
Penn launched his acting career in the early 1980s with ensemble roles in the military thriller Taps and the beloved comedy Fast Times at Ridgemont High, before turning toward serious roles and delivering riveting performances in State of Grace and The Indian Runner. His reputation as an actor grew alongside a reputation for violent outbursts that led to fines and even jail time. Those days are gone, he suggested, as Collins asked him toward the end of their chat whether he has mellowed over the years.
“I haven’t had a yelling match with anyone in four years,” Penn told her, then explained how this is possible. “I have not listened to anyone yell for more than two seconds before I walk away.”
As Penn entered the canon of serious Hollywood actors in the aughts with his two best actor wins, his name also became synonymous with speaking out about aid and outreach to devastated parts of the world. Over the years, he has put his money, time, and energy where his mouth is — arguably more than anyone else in Hollywood.
It’s been 16 years since Penn established J/P HRO in the wake of the catastrophic Haiti earthquake in 2010. The relief nonprofit was renamed Community Organized Relief Effort (CORE) and aims to bring immediate humanitarian aid and recovery to underserved communities across the globe, notably in war-torn Ukraine in recent years following Russia’s invasion.
The actor assured the crowd that the people of Ukraine are just like Americans, and that what is happening there is unimaginable and devastating. But he believes that ultimately the country will prevail over the Russian invasion, which has now stretched past the four-year mark.
As for this year’s Oscars, Penn revealed that he did, in fact, watch the ceremony from Ukraine. For him, the famously lengthy awards show ran all night and into the morning, with the broadcast starting around 2 a.m. local time and ending around 5 a.m.
“I really got to enjoy the Academy Awards for the first time,” Penn told the crowd. “It was great.”
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