Sean Penn on Marvel Movies: “It’s taken so long in the careers of so many talented people”


Sean Penn is sort of done with the movies. He still makes them here and there. But most of all, Penn sees the commitments he made years earlier. After those? He is not sure how much more he is going to play or direct.

Penn, the 61-year-old maverick actor and sometimes filmmaker, is in many ways thankfully out of step with most of the prevailing winds in Hollywood. Streaming movies? Franchise Movies? What is called “cancel culture?” All of these things attract his anger, to varying degrees. Meanwhile, Penn spends more time on Haitian relief efforts and vaccinating people than he does on movies.

All of this makes Flag Day, a new film directed by Penn and in which he stars, a rarity for a once voracious actor who, over the past decade, has only co-led in a few films (The Professor and the madman, Gangster Squad). In the father-daughter drama, which MGM hits theaters on Friday, Penn plays a larger-than-life but often absent and sometimes imprisoned father of his daughter Jennifer (played by Penn’s daughter Dylan Penn).


“I feel right now with this film that is incredibly lucky to have a film that is going to be a film, that is going to have a theatrical façade,” Penn said in an interview last month. “As an audience I can be very interested in some of the things that just broadcast. But as a practitioner, not at all. To act in something, you take it in a certain stride. But as a director, as I’ve always said: she’s not the girl I fell in love with.

Dylan Penn and Sean Penn Dylan Penn, left, and his father, Sean Penn, who also plays his father in the film, at the Flag Day premiere at the Directors Guild of America Theater. (Photo by Jordan Strauss / Invision / AP)

And Penn looks more and more like someone whose romance in the movies has faded. He misses Hollywood films that are not “just dazzling films, Cirque du Soleil films,” he says. On Marvel films, he laments “how much it has taken up space and taken so much time in the careers of so many talented people.” Arguing that today he would not be allowed to play gay icon Harvey Milk (Milk 2008), Penn recently said that soon only the Danish princes will play Hamlet.

And Penn’s generally well-regarded directorial career (including The Crossing Guard in 1995 and The Pledge in 2001, both with Jack Nicholson; and Into the Wild in 2007) has recently been more eventful. Her last film, The Last Face in 2016, starring Charlize Theron, failed and was loudly booed on her Cannes Film Festival debut. Yet last month, Penn returned to Cannes for the Flag Day premiere.

“I’ve been to such extreme ends on it. It’s like: whatever, ”says Penn. “The point is, I’m sure I know as much – more – about acting as almost any of these reviews. And I’m very confident in the performance that concerns me the most.


With that, Penn raises his hand and points to where Dylan is sitting across from an otherwise empty hotel bar off the Cannes Croisette. Dylan, 30, is the star of Flag Day. She’s already tried herself in the theater, but it’s easily her biggest role to date. In the film, adapted from Jennifer Vogel’s 2005 memoir Flim-Flam Man: The True Story of My Father’s Counterfeit Life, she plays an aspiring journalist with a rarely truthful father.

Penn’s confidence is not out of place. In Flag Day, Dylan is natural, poised and captivating. She already looks like a veteran, which one would expect from Penn and Robin Wright’s child. And these criticisms? Some have been quite complimentary. Variety said the film “reveals that Dylan Penn is a major actor.”

As Penn retires from the movies, his daughter steps forward, although she didn’t immediately seek the spotlight.

“Growing up, being around actors and being on set, that was really something that didn’t interest me at all,” says Dylan. “I always thought, and I still think, that my passion is to work behind the camera. But as soon as I expressed the desire to do that sort of thing, both of my parents said separately: you won’t be a good director if you don’t know what it is to be in the place of a actor.

Dylan admits his father may be “passing the torch a bit.” Hopper Jack Penn, his younger brother, also co-starred in Flag Day. (The rest of the cast includes Josh Brolin and Regina King. Original songs by Cat Power, Eddie Vedder and Glen Hansard contribute to the score.)

“I always thought if she wanted to do it, I would encourage her,” says Penn.

For Dylan, Flag Day’s father-daughter relationship – Jennifer tries to help and stabilize her scam dad, but also inherits some of her more destructive scam habits – is a half-reflection of their own bond together.

“She’s always strived to have this really honest and transparent relationship with her father, which she never got in return,” Dylan said. “I tried to have this with my dad and got it back.”

Penn recently shot Sam Esmail’s Watergate series for Starz, starring Julia Roberts. He said vaccinations should be mandatory for everyone on the set. During the pandemic, Penn’s Community Organized Relief Effort, a nonprofit, which it launched after the 2010 earthquake to help Haitians, erected testing and vaccination sites, helping distribute millions of vaccines.

Perhaps these experiences made Penn even more repelled by something artificial.

“My tolerance for the artificial is less and less,” says Penn.

But working with Dylan came naturally. Speaking of his attentive, even disarming, presence, he calls it “as simple as it gets.”

“I would kind of get caught up in that sometimes, like, ‘Uh, oh. She really listens to this. Does she see through this? ‘ Says Penn.

Penn started out younger – he was playing Fast Times at Ridgemont High when he was 21. He felt confident from the start in roles that resembled him – “young and very shy,” as he describes it. Staying natural while pulling away from himself, Penn says, has been the journey ever since.

“How do you feel so natural, so free in something where you’re going to play the part as in something where you bring the part?” With varying degrees of success and failure, that’s been the road – to find that original die-hard, ”says Penn. “There are things I see in Dylan that are so unmistakable.”


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