Sean Penn Is Cracking Dad Jokes and Trying to Save the World

"I am a dad who is trying to be a better dad every day."

by Donna Freydkin

Sean Penn. That name represents something very specific if you choose to believe what’s been written about him. A prodigious talent, to be sure. But in his case a rare gift coupled with a famed surliness, an intractability, a disdain for the press that goes hand-in-hand with a mercurial nature that makes interactions with him, shall we say, a bit precarious and unpredictable.

And then, there’s the Sean Penn who’s on Zoom on Saturday night. A deeply thoughtful, deeply polite, deeply curious man who, at heart, is one hell of a proud father who gets all — yes, we said it — mushy when talking about his daughter Dylan, 30, and son Hopper, 28, whom he directed and played opposite in Flag Day.

“I learned that I make some pretty miraculous children,” he says, in response to what he took away from the filming experience. “I always like to say that my kids must have gotten my looks because their mother kept hers.”

Yes, folks, that’s Penn, 60, cracking an actual bonafide joke about his ex, Robin Wright. The two-time Oscar winner often hailed as the best and most effervescent actor of his or any generation, doesn’t suffer fools, or, really, much of anything. One could argue fair play to him, because since 2010, he’s been too busy doing his bit to save the world, through his J/P Haitian Relief Organization, founded after the country’s devastating earthquake. Now known as CORE (Community Organized Relief Effort), its main focus has been on COVID-19 containment through testing and vaccination.

He doesn’t act much these days, but that’s him in Flag Day, in theaters Friday. Based on a true story, it tells the story of a con-man (Penn) who flits in and out of his kids’ lives, a charlatan “entrepreneur” whose emotional transience nearly destroys his daughter Jennifer (Dylan Penn). The movie is an unsettling exploration of what it means to be a parent, versus what it actually means to do the grunt work of parenting one’s children. On a Saturday afternoon, an upbeat Penn talks to Fatherly about being a dad, playing a dad, and directing his daughter.

Sean, I need to ask you first about the scene with your daughter in the diner, where she comes to live with you. It’s a hell of a complex scene, and she nails it. How did it feel, both as her dad and as the director, her boss?

It was the first scene that we did together. I think that in some part of one’s mind, you can’t help but be concerned about, are you setting your child up for failure. I had so much confidence in her, but then it was the extreme relief I had when I realized that she would exceed my confidence in this thing and be thrilling in it. And so it really set us off, I think, on a very good path because it was a very long scene. Right off the bat, she had come in with so much of it, in a way that was just disarming and beautiful.

Did the script just speak to you?

It’s as simple as I read a script I loved and the minute I read that script, I saw my daughter’s face planted squarely on the Jennifer character in a way that was it. I could not part with it.

How did you separate being Dylan’s dad, and being the director, the one who calls the shots?

It is interesting because there were many times where I felt — my running joke is that I felt like calling child protective services on myself when I was encouraging her or asking her by implication of having her do this role to dig into very painful places sometimes. Or even rageful places and things where you’re not seeing your kid look happy, which is all you ever want to do. So it took a little adjusting and recognizing that for her, like for many actors, that this was an outlet of an expression.

There’s an extraordinary power to Dylan. So I got over it. I got over child protective services and just looked forward to coming to work and seeing this young actress who had no contrivance in anything about her.

What kind of dad are you?

The very, very best. I am a dad who is trying to be a better dad every day. I think I was always dug in and had a very clear sense of my kids being my priority. But it is a job that comes without a manual. Especially because each family has its own dynamics. I felt really blessed with my parents, both my mother and my father, and saw a great example, but it didn’t automatically transfer to the dynamics that we had. So I like to think of myself as an improving father — I’m largely not ashamed of where I started.

Your children grew up as the offspring of famous parents. What values was it important for you to impart to your two kids?

There are the classic values and then there’s that they value each other, which I think is probably between their mother and I, the most successful element of what we did. They’re very close to each other. But you know, a pretty standard operating procedure in terms of honesty, manners, humility. And in both the case of my daughter and my son, I think I’ve been able to impart more to them than I myself managed at their age.

I know you’re a reluctant actor, you’ve said so yourself countless times. How was this experience for you?

It was so enriching to do, but I can’t describe it as enjoyment. There’s just no rewriting that. Thank God I got to have that experience, but acting is a struggle for me. I love directing so much that I would not have thought to interrupt that flow by acting, but it came out of practical necessity and some encouragement. I just sort of spontaneously jumped in at the last minute to do it. I’m really glad I did. I had a great time directing this movie. I don’t know if I can say specifically that I loved acting, though. I did love the dance with her, because I don’t have any rhythm in any of my cells for actual dancing, but I’ve got some reasonable amount of rhythm as an actor. And to be able to do that with my daughter was really exciting.

On a different note, you’re also deeply involved in CORE. Has your mission changed since you guys first started in 2010?

Well, certainly in the last year, we’ve become completely occupied with this pandemic as an organization. It’s been heartening to see how many people — we were an organization in the continental United States of seven employees and scaled up to 3,000 in 11 months.

And now we’re in the struggle. Everyone knows we’re in the struggle with vaccine hesitancy. There’s nothing I would like more than to be in the pandemic prevention business and in the programmatic we were involved in before the pandemic. But as long as there’s going to be a kind of arrogant radical libertarianism that’s going to be influencing people’s ignorance, we’re going to be up against it for a while.

And I see that you’re holding a mask. So you don’t feel that the mask is infringing on your personal freedom?

I don’t think that it’s okay to point a loaded gun in somebody’s face and anyone that’s not vaccinated is certainly, and even those of us who are vaccinated, can carry this thing. Until we quell it, it’s a very small price to pay or thing to ask people to do.

What have you learned about humanity since founding and running CORE? Has it made you more upbeat, or more depressed?

Well, the good, the bad and the ugly has all been enhanced in the experiences I’ve had with CORE but I try to keep focused on the good. That’s not always difficult to do. I’ve seen a lot of amazing people push through. Humanity is clearly at its own tipping point, both for the existential aspect of the environmental concerns and also with what this pandemic has come to, you know, be dancing with a kind of division in the country that I suppose existed when I was 11, 12 years old in the United States. There was a lot of division, but certainly, in my adult life, there’s been nothing like this. And it hasn’t hit its worst yet. That’s what’s concerning. I know it can get better if we get through the worst, but I worry about how bad the worst can be.

In terms of films, you’re also attached to Gaslit, opposite Julia Roberts. What’s the status of that?

I was working on a project with Julia Roberts on the Watergate story but I’ve taken a pause from that while they get their ducks in a row. I’ve got to keep focused on that first for when the time comes that the unions show some actual moral leadership and stand up with the studios to demand vaccination protocols.