Sean Penn on Following His Curiosities, Fighting COVID-19, and a Random Run-In With John Belushi Before He Died

Acclaimed actor, filmmaker, and activist also talks meeting Fidel Castro and working with Jack Nicholson

June 9, 2020

Between a pandemic which has already claimed over 400,000 lives and ongoing street protests over injustice and police brutality, the world needs as many heroes as it can get right now. Enter actor, filmmaker, and philanthropist Sean Penn, who in recent years has earned as many accolades for fearless activism as he has for contributions to the world of cinema. During his Stern Show debut on Tuesday, he acknowledged those two passions are at least in some small way connected. If nothing else, his show biz successes afforded him the opportunity to travel which has helped him broaden his worldview, rededicate himself to a variety of noble causes, and, in some cases, get audiences with contentious leaders like Fidel Castro and Hugo Chavez as well as the notorious drug lord Joaquín “El Chapo” Guzmán.

“What do you think drives you?” Howard asked. “Do you ever just say, ‘Shit, I got the greatest life … Why do I give a fuck?’”

“For me, a great life is to be able to follow one’s curiosities,” Sean said. “I’ve had the luxury, the benefit of being able to do that.”

Over a decade ago, Sean’s daughter Dylan Penn accompanied him on a trip to Havana. She was only 14 at the time but he took her with him to meet Castro. As the story goes, she refused to shake the Cuban president’s hand because she objected to his human rights record.

“I thought that was fantastic for a kid,” Howard told Sean.

“I must say, I was very proud of her,” Sean replied. “And [Castro] was not defensive … He was a very, very practiced politician … He expressed regrets. It was a fascinating dialogue.”

Howard praised Sean for his willingness to explore places so many other people with privilege might purposefully avoid, but Sean remained self-effacing. “I find it easier to focus on books when you’ve been in the places where they’re about,” he said.

“I have found my way to a lot of places where leaderships are rightly or wrongly demonized by the American perspective … One of the perks, I suppose, of being a known person is often I’ve had access from, you know, the bottom of society to the top of government in countries,” Sean continued, adding, “Good or bad, it never plays out the way one originally perceived it.”

Sean and Community Organized Relief Effort (CORE), an organization he founded a decade ago, have provided much-needed assistance in countries like Haiti and Pakistan as well as in New Orleans after Hurricane Katrina. The entertainer has also been outspoken about various social causes and even once helped an American get released from a Bolivian prison.

These days, CORE is focused on assisting state and local officials as they administer free COVID-19 tests in places like Oakland, Los Angeles, Chicago, and the Navajo Nation. The organization has a staff of over 1,000 people across the country and works closely with everyone from California Governor Gavin Newsom and Los Angeles Mayor Eric Garcetti to New York Governor and recent Stern Show guest Andrew Cuomo.

Howard believed Sean and his organization’s efforts were praiseworthy, but he was admittedly concerned by the notion that a country as mighty as the United States had come to rely on an entertainer during a health crisis. While Sean did rebuke the federal government’s slow and disorganized pandemic response, he told Howard he believed civic action was a vital component of any relief effort.

“I’ve been steady working on this stuff for about 11 years now and I’ve never seen a disaster anywhere in the world, including the United States, where if all things were present—all the best leadership, all the resources deployed properly—that would be enough to handle all the needs of the people that were affected in that area,” he said. “So, this does take citizenship participation.”

Sean supports the ongoing protests against police brutality, but he and his organization are also concerned with keeping demonstrators safe as a pandemic rages on around them. “We consider ourselves at CORE pro-test protest,” he told Howard. “[It’s] an overall noble mission that I think is going to make a change for the better. How much more powerful a picture that would be and how much larger a footprint they would have if they just distanced six feet with a mask on.”

The actor and activist thought the world was at a crossroads. “I don’t sense that the protests are going to stop soon. I think that they are a fundamental part of us moving forward,” he said. “It’s an existential moment … Read a history book. It’s either going to invigorate or depress you, but it’s not going leave you in a grey zone.”

As dire as things may sometimes seem, though, he told Howard he believed society is finally on the right track. “I’m not prone to whimsical optimism, but I think we are on our way to a better world than I’ve seen,” Sean said.

His COVID-19 efforts may have been the topic de jour, but Howard wasn’t about to let his guest leave without spending at least a few minutes talking about his incredible Hollywood career. At one point, Howard wondered if starring in “Milk,” the acclaimed 2008 biopic about openly gay activist and politician Harvey Milk, was one of the high points on Sean’s already impressive entertainment résumé.

Sean said the project was one of his favorites, crediting both Milk’s incredible real-life story and filmmaker Gus Van Sant’s masterful direction. “He has that, you know, rarest human quality of humility and yet incredible talent,” Penn said of Van Sant.

“Harvey Milk is a character, such a touching, intelligent guy,” he continued. “I increasingly, as I was moving toward this movie, just felt this sorrow that I’d never get to meet him,” he later added.

Large portions of “Milk” were filmed in San Francisco’s Castro District, one of America’s most prominent gay neighborhoods. Sean recalled his driver helping him get into character as Harvey Milk each day by putting on a certain song as soon as they set eyes on the Castro. “He’d hit the CD and we’d be blasting ‘It’s Raining Men,’” Penn recalled.

“That gets you into it, huh?” Howard laughed.

“I was right there. I was going to dance with the fellas—you bet,” he said.

Sean has five Oscar nominations for Best Actor in a Leading Role and won twice for “Milk” and “Mystic River.” Howard was curious how winning an award on Hollywood’s biggest night compared to some of his philanthropic honors, like the Peace Summit Award.

“Honestly, I’m going to tell you. In their own way, the predominant response [to winning any award] is a certain kind of embarrassment,” Sean said.

The Oscars in general, he explained, are more about celebrating with colleagues. “The dominant feeling is relief, not so much a kind of excitement or that,” he said. “It’s not a bad feeling—it’s nice to have things acknowledged.”

Sean said the relief is rooted in not letting down everyone who worked hard on the project, including not only cast and crew but also the team who helped promote the film. “The dirty little secret in Hollywood is that not all the suits are assholes. There’s caring, creatively minded people who embrace a film … They’ve given a lot of commitment. You become, even if temporarily, quite close to them,” he told Howard. “That’s what the celebrations are for … It’s a bonding moment.”

Sean has starred alongside countless talented actors over the years. He’s also directed several of them, like Dennis Hopper in “The Indian Runner,” Hal Holbrook in “Into the Wild,” and Jack Nicholson in both “The Pledge” and “The Crossing Guard.”

Howard wondered what it was like, in particular, to direct Nicholson.

“He is a director’s dream, an angel on your shoulder. There’s a world in my imagination where I just would’ve made movies with Jack for both of our lives,” Sean told him.

While Sean never had the opportunity to work with John Belushi, he did recall a chance encounter he had with the late actor and comedian one night in Los Angeles in the early 1980s. It happened at a time when Sean and his “Taps” co-star Tom Cruise were on the rise and being courted by movie agents. After a late dinner with a potential agent, Sean recalled two men driving up to them in a convertible. The first person he recognized was “Saturday Night Live” cast member Don Novello.

“I’m thinking, ‘The passenger in that car [plays] freaking Father Guido Sarducci,’” Sean recalled.

Next, he noticed the driver. It was Belushi, an even bigger “SNL” star. Belushi asked a not-yet-famous Sean for directions to Chateau Marmont, a popular hotel and hotspot which incidentally also happened to be the place where Belushi was later found dead.

“They pulled over, eight feet away from us, and asked directions,” Sean told Howard. “I said, ‘You know where the Chateau Marmont is,’ and [Belushi] laughed and they pulled away.”

“Taps” may have been Sean’s first major movie but many consider his breakthrough role to have come in Amy Heckerling’s 1982 high school comedy “Fast Times at Ridgemont High.” Penn starred as the perpetually stoned surfer Jeff Spicoli. Nearly 40 years later, the film is a cult classic and Spicoli remains one of the most beloved characters to emerge from the genre. Later this month, Sean is slated to take part in a star-studded virtual table read of the film’s Cameron Crowe-penned script. It’s an effort to raise money for CORE.

Howard gushed about his love for Spicoli but was shocked to learn Sean won’t be the one reading his lines at the virtual table read. As Penn explained it, however, he is happy to finally be on the outside looking in. “From the very time that I read the book, the character Spicoli made me giggle. I have an opportunity now to sit back and see it,” he said, adding that he isn’t yet revealing which part he will read.

Sean credited comedian Dane Cook with organizing the virtual table read. “He’s the one who put this thing together … He came out of the trees for a grant with us when we first started the COVID testing,” Sean told Howard. “He’s got an extraordinary group of people, so I think it will be a lot of fun and maybe a breath of fresh air during the course of all of this.”

“Sometimes it’s nice to have dessert with your meal,” he finished.

Click here to volunteer with or donate to the Community Organized Relief Effort (CORE) and get updates on Sean’s “Fast Times at Ridgemont High” virtual table read here.

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