Sean and Dylan Penn on Flag Day: ‘It did feel like going through therapy’

The Hollywood heavyweight returns with a triple threat in ‘Flag Day’, which he directs and stars in alongside his two children. James Mottram meets him and daughter Dylan to talk about movie-going, making films with family and ‘white male entitlement’

‘Sometimes people take their privilege and freedom as a right to be anti-citizen, to be failed citizens’ (MGM)

“I found myself falling into a once-in-a-lifetime experience that I wouldn’t miss for anything,” says Sean Penn, assessing his latest film as director, Flag Day. You can put that down to casting his kids. In the past, he’s directed some of the world’s finest actors. Viggo Mortensen starred in his 1991 directorial debut The Indian Runner. Jack Nicholson took the lead in The Crossing Guard (1995) and The Pledge (2001). But this time he turned to Dylan and Hopper, his two grown-up children with his actor ex-wife, Robin Wright.

It’s 10am LA time and I’m chatting with Sean, 61, and daughter Dylan, 30, over Zoom. She’s stationed in a tiny featureless room, sipping from a huge mug, her long, blonde hair falling over her grey sweatshirt. The likeness to Wright is startling. “She has her mother’s skin,” her father remarks at one point, in that familiar low growl of his. He’s dressed in a navy blue T-shirt, curls of smoke occasionally rising past his face from the lit cigarette he’s got on the go. A golden retriever mooches in the kitchen space behind him.

Rebounding from the unmitigated disaster that was his last directorial outing – 2016’s aid worker drama The Last Face, a film that was roundly booed in Cannes when it premiered – Sean has found his footing again with Flag Day. Perhaps that’s because it’s a tale close to his heart. A true story, based on the book Flim-Flam Man: The True Story of My Father’s Counterfeit Life by Jennifer Vogel, Flag Day is a quietly told father-daughter character drama told from Jennifer’s perspective. She recounts her childhood and young adult years as she begins to realise her father John Vogel – played by Penn Senior – is a major con-artist. “It’s a great story of truth and deception,” he remarks.

He gave the book as a gift to Dylan when she was 15, and asked her if she’d consider playing the young Jennifer on screen. She’d never acted before. “I did not want to do it,” she says. “I never wanted to be in front of the camera. I never thought of myself as an actor.” It wasn’t that she’d kept away from the business; the whole family was steeped in it. Her grandfather – Sean’s father – was actor and director Leo Penn. Her grandmother – Sean’s mother – Eileen Ryan also acted (and has frequently appeared in her son’s films), while Robin Wright has seen a career stretch from The Princess Bride to House of Cards.

For Dylan, who grew up away from Hollywood in the quiet area of Marin County, north of San Francisco, there were visits to her parents’ sets, including 2007’s Into the Wild. This adaptation of Christopher McCandless’s memoir about dropping out of society and finding nature, which her father directed, remains a vivid experience. “Not only because I had a massive crush on Emile Hirsch [who played McCandless] at the time,” she laughs, “but travelling to different states to see my dad and being in Alaska…”

She left home at 18, and grafted – jobs as a waitress, barista, and pizza delivery driver. There was a spell modelling and a period assisting on TV and music video shoots. Over the years, she had thoughts about working behind the camera, but in front of it? She felt acting was rather silly – adults playing dress-up. But gradually she changed her tune. In 2015, she made her screen debut in a horror flick called Condemned. There was a bit-part too in Elvis & Nixon, a film with Michael Shannon and Kevin Spacey.

Her dad, meanwhile, had not given up on the idea of Flag Day. Initially, he was going to star, with Alejandro González Iñárritu, with whom he made 2003’s 21 Grams, directing. But when that floundered, he took it on as director and went back to Dylan. As much as he didn’t want to put his daughter on the stage, he couldn’t shake the idea of her playing Jennifer. “I didn’t get very deep into it before Dylan’s face became such an indelible part of my connection to the storytelling. The kind of ‘truth machine’ that she is… I found it very moving.”

Then, at the risk of seeming nepotistic, he also cast Dylan’s younger brother Hopper – now 28 – as Nick, Jennifer’s sibling. And he was forced to play John Vogel himself, much to his chagrin apparently, after another actor “fell out” at the 11th hour. “I would be very reluctant to act and direct again,” he insists. “I don’t think I’m particularly wired for it and I found it an exhausting two jobs to do at the same time. But that said, I’m thrilled that it happened because I was able to have that experience both with Dylan and Hopper.”

Penn won a best actor Oscar for 2003’s ‘Mystic River' (Warner Bros/Kobal/Shutterstock)

Regardless of this dislike of movie multitasking, Sean has created another memorable character to add to an already astounding body of work. Between 1996 and 2009 alone, he accumulated five Oscar nominations and two wins, for Mystic River and Milk. Steering John from the mid-Seventies to the early Nineties, as he drifts in and out of Jennifer’s life, Penn offers a tender portrayal of a con-man whose biggest victims are probably his own family. He’s gentle and well-meaning but also self-delusional and a scoundrel.

“Rather slippery, wasn’t he?” adds Sean, with relish. “I think, in some ways, quite sophisticated. And yet in others, quite childlike.” He feels that John has something in common with the “white American male entitlement” that he sees around him in so many today. “Or rather, I should say, [in the] belief that this American Dream that was promised [to] them entitles them to it. And that is a very hard wiring to correct.”

Sean has played a broad spectrum of white American males, entitled or not – from his gung-ho soldier in Casualties of War, via his openly gay San Francisco mayor Harvey Milk, right up to the lascivious director he inhabits in Paul Thomas Anderson’s latest Licorice Pizza. But when it comes to how he views masculinity, he is old school. He recently told one newspaper: “I am in the club that believes that men in American culture have become wildly feminised… I don’t think that [in order] to be fair to women, we should become them.”

What did he mean by those comments? “I think that men have, in my view, become quite feminised,” he reiterates. “I have these very strong women in my life who do not take masculinity as a sign of oppression toward them. There are a lot of, I think, cowardly genes that lead to people surrendering their jeans and putting on a skirt.”

It’s an answer that suggests he would prefer masculine and feminine traits to remain as such, and one that leaves Dylan quiet, staring into space. I’m left wondering how much their relationship compares to the Vogels? “I think in our own relationship with each other, I’m far more handsome,” he dad-jokes. “Of course, there are parallels. We would run into things that came close to the bone here and there… that was easy for us both to look each other in the eye and go, ‘I remember we’ve been there’ and so on.”

Sean and Dylan in ‘Flag Day' (Vertigo Releasing)

Penn senior, it seems, is granite-carved from another era. He grew up in California, surfing the Pacific waves when he wasn’t making short movies with high school buddies Charlie Sheen and Emilio Estevez. Movies were high art then. Even the very notion of watching Flag Day on digital is hard for Penn to accept. “Going to the theatre and experiencing something in a moment with strangers is the girl I fell in love with,” he says, simply. Dylan, at least, agrees. “The experience of being in a theatre is so different from being in your bed watching it on a laptop,” she says.

When Flag Day was released in America, Penn made it clear that he wanted the film to be seen in cinemas, but only if ticket-buyers were vaccinated against Covid-19. “I mean, what value are we to ask people into a theatre to have a growing experience – or we hope it can be – if their body is being affected in a degraded way?” he tells me. “So yeah, we all have to be thinking about that and in doing so, get through this so that going to the theatre is not a reluctant experience anymore.”

He has “enormous faith in the vaccinations” and speaks witheringly about living in a “privileged country” like America, where there is not only a surplus of vaccine shots but also an ignorance towards the science. “Sometimes people take their privilege and freedom as a right to be anti-citizen, to be failed citizens – those who will search out the kind of bogus science that would give them legitimacy [when it comes to] not being vaccinated.”

His non-profit CORE (Community Organised Relief Effort), which he founded in response to the 2010 earthquake in Haiti, has devoted efforts since the pandemic broke to Covid-19 testing and vaccinations. In the past, the actor has been lampooned for his activism (not least in puppet satire movie Team America), but he’s never relented. “We plug along,” he says, a chink of optimism in his voice. “We continually try to educate and to incentivise more people to accept the vaccine. And we advocate for the distribution of vaccines in places where people are hungry for it.”

Away from this, he’s next set to make a rare appearance in a limited TV series – Gaslit – which deals with the Watergate scandal. Even he has to admit that the small screen has eclipsed the big this century. “I’ve seen such extraordinary things on television,” he says. As for Dylan, she wants to turn this “once-in-a-lifetime experience”, as Sean puts it, into something more regular. “It did feel like going through therapy every single day,” she chuckles, softly. “But it’s definitely made me want to take more chances.” Like father, like daughter, you might say.

‘Flag Day’ is released in cinemas and on digital 28 January