Sean Penn and Dylan Penn Make ‘Flag Day’ a Family Affair

MALIBU, Calif. — Sure, Sean Penn has two Oscars. But at home, his children Dylan Frances Penn and Hopper Jack Penn wanted to pelt him with tomatoes.

“I tell jokes terribly,” Sean admitted. “They always tell me, ‘You probably should have stopped there.’”

“As you do with your dad,” Dylan added, rolling her eyes affectionately. Despite her father’s failings as a stand-up comic, she trusts him as the director who could kick-start her acting career — if she wants one. “Flag Day,” which premiered in competition at Cannes and is in theaters Aug. 20, stars the two in an adaptation of the journalist Jennifer Vogel’s memoir, “Flim-Flam Man,” about her shaky young adulthood in the orbit of her charismatic con man father, who died following a high-speed police pursuit.

Sean handed Dylan the book when she was a teenager. She passed. Now 30, she took nearly 15 more years to agree to make the film, long enough for her 61-year-old father, Sean, to come around himself to doing double-duty as director and leading man, the first time he’s tried to do both. “I don’t think stereophonically,” Sean said.

He had an easier time convincing his son, Hopper, to sign on to a small role as Vogel’s brother.

“He just asked me to play Nick and that was that,” Hopper said by email.

Sean and Dylan were sitting in their front yard in the shade of an Airstream trailer named Las Vegas, in honor of Sean’s intended elopement to Leila George. (Because of the pandemic, the couple was instead married by a county commissioner over Zoom last summer as Sean’s nonprofit CORE opened a Covid-19 testing site at Dodger Stadium that has since evolved into a fleet of mobile vaccination units.)

Alongside three large dogs continually changing their mind about where to nap, the two talked over each other, and indulgently allowed themselves to be interrupted, as they hashed out their maturing relationship. “I know what the stamps are in her passport — and she knows mine,” Sean said. “And it was thrilling that we were able to transfer it to a movie.” These are edited excerpts from the conversation.

This is a film about finding your own identity apart from your parents. Dylan, you avoided acting. You worked at an ad agency, you helped edit scripts, you delivered pizzas — how were your tips?

DYLAN PENN Terrible.

SEAN PENN That terrified me. All those frat houses around U.C.L.A.

DYLAN I started modeling like six months into being a pizza delivery girl. I would work at night doing pizza deliveries, but during the day, I was doing full hair and makeup for a shoot. So I would show up to these frat houses and they’re like, “Oh, did someone order a stripper?” Nope! Just a pizza. I always thought I would be in the film industry, but I expected to be behind the camera. When I was, like 15, 16, the first time you came to me with this project, I just felt like it was a really silly thing to do.

Acting?

DYLAN Adults dressing up as different people. The real reason that I got into acting in the first place was because I told my parents [her mother is the actor Robin Wright] I wanted to direct eventually, and both of them told me that I should know what it’s like to be an actor before I direct so that I know how to direct an actor.

Was this film always going to be the two of you?

SEAN I was going to be involved in it first as an actor. She didn’t feel ready for it. And then when it came back around, it came to me as a director. So then I was just going to direct it. And then we got into a bind about a month out from shooting, and I had to just jump in and I’m so glad that I did.

DYLAN It was a real shock because we’ve never worked together. The idea of him directing me was already like a big undertaking. The idea of being so vulnerable with your own family in front of 40, 50 crew members is daunting.

SEAN Your dirty laundry is going to be aired on a daily basis. I don’t mean your family history dirty laundry, but I mean that day’s emotional interactions with each other. But on the upside, I’ve never been so excited on any movie set as when I was in a scene with her, or just watching her kill it. In particular, the thing that all actors say, but very few do, is that listening is everything. She listens in a way that I love watching because she doesn’t tell you what she’s thinking. I like putting the camera close on her because she’s not going to wink at you.

What about Sean as a director makes him unique?

DYLAN His vision is so fully realized ahead of time. Even working in a space where, financially, it was a bit of a constraint, there was no limit to making that vision become a reality. A prop, a location, my hair. Literally, the opening where Regina King and I had a scene together. I walked in and he was like, “You would not be wearing mascara.” And I remember being so pissed. It was a fight for 10 minutes to take the mascara off.

SEAN It was a two-and-a-half-hour standoff.

DYLAN I was wrong. But I’m stubborn and it was a fight.

SEAN I will just say on your behalf, a lot of times where she had a different view, more often than not, I came around to thinking that she had the right idea. So I would be very interested in seeing the things that she directs.

Acting dynasties go back to the Barrymores. But it feels like your family is shaping a directing dynasty. Dylan, both of your parents released films in the last year that they directed, and Sean, your father, Leo Penn, was a director.

SEAN I spent a lot of time with him as a kid on sets. TV one-hour dramas. He was much more patient. A gentler sort. But I’m sure that a lot of my general sense of what a director’s job is comes from him.

And he directed you in “Little House on the Prairie”?

SEAN That was summer money as an extra as a kid. I didn’t think I wanted to get involved in film until senior year of high school.

And “Judgment in Berlin” [a 1988 film that featured Sean as a trial witness].

SEAN That was a great experience. We talk about in this story, how much of your parents do you really know? The deceptions in the relationship between John and Jennifer — from John to Jennifer.

Even with a gentle, open, loving man, it took going to Berlin, knowing [that during World War II] he’d flown those low-altitude bombing missions virtually where we were, and walking with him through a square where mothers are pushing strollers. I won’t call it regret by any means, but the humanization of what he’d done from the air had wiped him out.

Getting to know one’s parents makes me think of Dylan’s Instagram post from a couple of years ago of your dad’s first wedding day.

DYLAN It was the first time that I realized, “Oh, my parents are people without me.” And this is like on a deep level, after going through a lot of family therapy. I get asked so much, “Wait, so you’re Madonna’s daughter?” Oh right! He was married to her — they had a life together.

You were 5 when you left Los Angeles and moved to Northern California. Just before, your mother was surprised by people with guns in your driveway. Do you remember that?

DYLAN I remember it vividly. It was me, my mom and my brother in the car. We pulled in around 10 p.m. and these two guys were standing in the driveway. My mom just said, “Don’t get out of the car. Don’t make a sound.” She got out and they pointed a gun at her stomach and she threw the keys in the bushes and yanked us out of the car. That superhero thing that moms take on when their children are in jeopardy.

SEAN And then they took the car.

DYLAN They crashed.

SEAN They finally crashed into a dumpster and took off running. They actually caught the second guy with a heat sensor from the aerial unit. He had gotten into a dumpster himself, but because he’d been running, his body was hot and they were able to see his heat.

DYLAN [This is one] reason my mom has said she didn’t want us growing up in this paparazzi frenzy that L.A. was becoming. Now, it’s beyond what it was in the ’90s.

It’s pretty impossible for anybody not to remark on how much you look like your mom. On the inside, do you see your dad?

DYLAN Oh my God. I feel like we’re both very alpha personalities, but with that, also being introverted in terms of our private life. I think a lot of my strength comes from watching my dad. My mom, as well, but just in different ways. I also think we see things in similar ways and emotionally react similarly, just in terms of, like movies that we watch, that we cry at —

SEAN Everything.

DYLAN It’s like what a lot of people have with their best friends. You both observe the same things.

SEAN Through a similar lens.

DYLAN Yeah, through a similar lens.

Some of these scenes seem like they would have been hard to shoot, really harrowing. You’re recording her as she’s watching you die onscreen.

DYLAN It’s an awful thing to watch. It was the first time that I felt 100 percent like my dad is not there — this is my dad — and I really felt like he was shooting himself in the head. I was crying and I could hear him crying behind the camera.

SEAN Watching you cry over me. [Fake sobbing] It’s so sad to see you lose your father!

You were crying, too?

SEAN She made me cry a lot. She makes me cry a lot. You kind of feel like somebody should call Child Protective Services on you for directing. What are you putting your kid through?

There’s a line in this film: “I think the greatest hope a man can have is to leave something beautiful behind — something he made.” Am I alone in thinking that line had a resonance for you?

SEAN Oh, no. It has resonance for me as you say it. Yes. Listen, I don’t know what else I was doing here. Now with two kids that I feel so proud of who are already accomplishing things out of their own gifts. On a beautiful day, despite a pandemic and everything else, you kind of go, it’s all gravy from here. Knock wood. [Knocks on a palm tree] But no question, I would be lost without ’em.