By Shay Moser
Double-Oscar winner Sean Penn is known for playing deeply intense characters. But the Mystic River and Milk star is just as known for using his Hollywood influence to organize and encourage political and social change around the world.
Evolving from an early television appearance to becoming a two-time best-actor winner and prominent activist, Penn has always been in the limelight for his roles and responsibilities.
Acting is in Penn’s Blood
Born in August 1960, Penn was raised with his three brothers in Santa Monica, California, by actor and director Leo Penn and actress Eileen Ryan. A few of his now-famous childhood friends included Emilio Estevez, Charlie Sheen, Robert Downey Jr., and Rob Lowe.
While Penn had parents in the film industry and grew up around friends with ties to the business, he hadn’t considered acting.
“I grew up going to sets sometimes with my father, and I found it all very interesting, but it never occurred to me to be part of filmmaking in any capacity,” he told MakingOf.
One of Penn’s early experiences was when he appeared in a 1974 episode of the Little House on the Prairie TV series as an extra when his father directed some of the episodes.
He officially entered the industry in an off-Broadway play in which he was spotted and chosen for the action-drama Taps, where he played a military high school cadet in the 1981 movie. His role as an underachieving surfer in the 1982 film Fast Times at Ridgemont High followed, and his career took off after his 1983 role as a troubled youth in the crime drama Bad Boys.
Penn’s acting work paid off in the 1990s when the Academy Awards nominated him for two roles. Penn also made his directorial debut and directed music videos during this time.
Penn’s third Oscar nomination came in 2001 for the drama I Am Sam, and he finally won for his part as a grieving father in the mystery drama Mystic River in 2004.
He attended the Oscars for the first time in the four times he’d been nominated. An opponent of the war in Iraq, Penn added a side of politics into his acceptance speech.
“If there’s one thing that actors know, other than there weren’t any WMDs, it’s that there is no such thing as best in acting,” he said, referring to weapons of mass destruction. “And that’s proven by these great actors that I was nominated with.”
He won his second Oscar in 2008 for his portrayal of a real-life politician and gay rights icon in the documentary Milk. “I did not expect this and … I know how hard I make it to appreciate me,” the outspoken Penn told the audience as he collected his award.
Penn played a diverse range of film roles until his satirical novel, “Bob Honey Who Just Do Stuff,” was published in March 2018. He told Vogue that he no longer had “a generic interest in making films,” and that being a writer will “dominate my creative energies for the foreseeable future.”
But Penn was inspired by his newest movie Flag Day, which was released in 2021. It was a family affair, too, as he starred with and directed his co-star daughter, Dylan Penn, 30. His son, Hopper, 28, also appeared in the movie. Both are Penn’s children with ex-wife actress and director Robin Wright.
“It’s been such a joy. And when we were shooting, we also had Hopper Jack with us. So, it’s been a great experience top to bottom,” Penn told USA Today about filming with his kids.
Getting to the Core of Penn’s Activism
The other constant in Penn’s film career was and is his support of numerous political and social causes. From criticizing President George Bush to supporting same-sex marriage, Penn has gone with his heart and head to live well by rolling up his sleeves and putting his time and talent where his mouth is, in addition to his money.
One well-known example came on the heels of Penn’s Mystic River win in 2005 when Hurricane Katrina hit New Orleans. Frustrated by the search and rescue efforts, he launched a rescue mission, saving 40 stranded locals.
“As it turns out, you feel you can fix it,” he told Oprah. “And I guess I am drawn by that because I feel I can offer something that way, and as it turns out I’m good at choosing people who can do what I dream about getting done.”
After the 2010 Haiti earthquake, Penn founded the non-profit organization Community Organized Relief Effort (CORE, formerly J/P Haitian Relief Organization) to distribute aid and, as the organization grew, free COVID-19 tests and immunizations.
“It’s not enough to just be an artist,” Penn said in an interview with Variety magazine. “I think, in Haiti, that’s how I finally felt. I had other stuff to give. And so, I found a place to do that.”
CORE has most recently been in Ukraine and neighboring countries providing humanitarian relief to those devastated by the fatalities and war. Penn even loaned Ukraine President Volodymyr Zelensky one of his Oscars in November.
“It’s just a symbolic silly thing, but if I know this is here with you then I’ll feel better and stronger for the fights,” Penn said in a video shared by Zelensky’s office. “When you win, bring it back to Malibu.”
Penn shows that life is much more than mere existence. In his eyes, to live means to participate in life by speaking up for others and acting — not only on screen but by taking action on political and social changes globally.
“Our soul as America is lost,” if Americans allow the Ukrainian people to fight alone, Penn released in a statement.
Join Penn in supporting communities worldwide: coreresponse.org