‘It Just Felt Right’: Actress Dylan Penn On Working With Her Dad in the Cannes Drama ‘Flag Day‘

When Dylan Penn was 15, her father, Sean, gave her the book Flim-Flam Man: The True Story of My Father’s Counterfeit Life, a memoir by journalist Jennifer Vogel chronicling her tumultuous relationship with her father. “I thought the reason he wanted me to read it was to help him figure out who should play Jennifer [in the film adaptation],” Penn explains from the sun-drenched Hôtel Martinez bar in Cannes, where her film, Flag Day, had premiered a couple of nights before. As it turned out, her father, who both directed and co-stars in the film, had his daughter in mind for the role from the get-go. Yet it wasn’t until a decade later—and with encouragement from her mother, Robin Wright—that Penn, now 30, signed on for her first lead role. (Previously, she appeared in the 2015 horror film Condemned and 2016’s Elvis & Nixon.) Flag Day follows the on-again, off-again relationship between Vogel and her erratic, conman father, John (Sean Penn), over the course of two decades. The film also features Penn’s brother, Hopper, as her on-screen brother, and is scored with original music by Cat Power and Eddie Vedder.

Vogue sat down with Penn in Cannes to talk about getting the part, the best advice Sean gave her on set, and channeling her past.

Vogue: I read that you always wanted to be behind the camera rather than in front of it. Is that true?

Dylan Penn: When I was young, I told my parents I wanted to direct. On separate occasions, both of them advised that I should know what it’s like to act before I direct, so I’d know what it’s like to be in the actor’s shoes. So I did a lot of assisting on movie sets for a while [as a production assistant]. I did a lot of music videos and a couple of TV shows and some print shoots. I felt more in it than when I was visiting my parents on set.

So when did you start to consider acting?

I just never thought of myself as an actor, and honestly, from a young age, I always thought it was really silly that adults dressed up and played different people. I have a very different view now, but [at the time] I wasn’t interested in anything in front of the camera.

So how did you end up taking on Flag Day?

When I was 16, my dad came to me with the part of [a young version of Jennifer] because he had an option on the script, and I said no. I was 27 when the script came back around, and I felt like I had more to offer because I could reference my own life experience to develop the character of Jennifer. My mom was the one who told me that working with my dad as the director was the best experience she’s ever had, which was what propelled me into this project.

Penn with her parents, Robin Wright and Sean Penn, c. 1990.

Photo: Michael Tighe/Getty Images

What did your mom say, exactly, that convinced you?

She said he was a really great collaborator and she felt like he created a really safe environment to be vulnerable on set, and that he was a hands-off director. She said you had a lot of space to play around and figure it out on your own. But I was really apprehensive at first. I felt a huge responsibility to Jennifer to portray her in a good light, and it’s a heavy story. I was nervous, and I know professional relationships with family can be really complicated. My dad and I have never worked together. So there was a lot of fear of the unknown going into it. But I also wanted to do it because I hoped it would make me a better director when that day comes, and the role is incredible and her story is so amazing. I feel like it was almost nostalgic because I first read it when I was so young. I related to Jennifer in terms of trying to find her own identity separate from her parents’ and not letting her past define her. I just felt like it was something that I could do.

What kind of conversations did you have with your dad that convinced you to make Flag Day?

He didn’t tell me this when I was 16, but he told me this time around that the first time he read the script, he always saw my face in the character. I felt he wasn’t setting me up to fail because he always has really good instincts, so I felt like I could ride with that. And then from the first day [on set], I knew things were going to go well. It just felt right.

I can’t imagine what it would be like to act on screen with my dad while he’s pretending to be someone else’s dad, and I’m his fictional daughter, because you can’t not see your dad when you look into his eyes, right? It must have been such a head trip.

I know, but it was actually pretty seamless. I do feel like my dad has a lot of attributes that John had. He’s really charming and adventurous and would do anything for his kids. I feel my dad was destined to be a father, so I didn’t feel like it was a real stretch. The only real difference I saw is that I have a really transparent relationship with my father, and Jennifer’s dad never gave that to her. [My dad] was just really fun to act with and gave me so much to work with. He’s really the only light part of this film.

When you were reading the script, were there any particular scenes that you felt might be challenging?

The only scene that I was really scared of was when I see John shooting himself on live TV when I’m watching the car-chase scene in the diner. I was nervous about that because I had been on set that day, so I saw the stunt doubles flipping the car, but I hadn’t seen my dad’s character shoot himself in the head. So that was all live for me. I was scared that I wasn’t going to be able to get that emotion, but it was actually just so shocking and very real to me.

When you saw that, did you see your dad or John Vogel?

I saw my dad.

That must have been really harrowing.

Yeah. He was also crying behind the camera watching me act out the scene. I was a lot—it was a lot.

Was there a piece of advice your dad gave you that stuck with you?

I have to say, he was pretty hands-off for the most part, which was really nice. His one piece of advice that became my mantra throughout the film was: If anything feels false, whether it’s something you’re saying, the way you’re moving, or the prop you’re handling, whatever it is, don’t do it, because it’s going to read false on screen. Every time they would call action, that was what I was saying in my head and I feel that really helped.

Sean and Dylan Penn at the photocall for Flag Day in Cannes.

Photo: Getty Images

Was there a fair amount of improvisation, then? A chance to feel it out?

Yeah, the script was more of a guide. We definitely stayed true to the story, but a lot of the dialogue is improvised. We also had a lot of time to rehearse—a week before we started shooting, we went to every location and rehearsed the scene so that on the day it felt so natural and familiar, and you could really just focus on the emotion. It kind of felt like what I imagine rehearsing for a play would be like—really feeling your set. I’ve never done that in any other movie.

Your character does a kind of 180, in that she goes from struggling with drug abuse to getting sober, getting a job, and generally taking control of her life. Did you go through anything similar in your own life that you could draw from?

There was a period of time right after I stopped modeling when I moved to New York for a guy and I didn’t have a job. I was 25, and I was there for a year, and he was working nonstop and I kind of started living a double life. I was kind of like his—I don’t want to say “arm-candy,” because we had a real relationship, but he just wasn’t really present. When he would go to work, I would go off and do a lot of drugs and drink a lot, and I was out with people that weren’t friends of mine. I ended up getting sober, and I did a 45-day stint in an all women’s group therapy healing center in Arizona, which was really life-changing. And after that I did a year and a half of sobriety just to see how I felt. And I think that really changed who I was at my core. It’s something that I’m really grateful I did at a young age, because it really set me up for the rest of my life.

Did you bring that experience to Jennifer’s character?

Yes, especially when she was younger—doing drugs and partying and trying to escape her reality. I completely remember that. It feels so far removed from me, but I could really tap into that time in my life, especially when she goes to college and tries to find out what her purpose is. I think that really came to me after I did this 45-day stint.

What did you do after the 45-day stint?

I did a halfway program for two months, which was really intense. Then I moved home, and that’s when I decided to continue my sobriety.

Are you still sober?

No. I don’t do drugs anymore—they don’t really interest me. But my relationship to alcohol completely changed after I did a year and a half of sobriety. I never drank or did drugs by myself, but I really missed the social aspect of drinking.

What was the most surprising thing that you found out about yourself on set?

I was really surprised that I could tap into a dark place really easily. I was in a really good place in my life during filming. I became really close with the crew and obviously my brother was there, so to switch from that happy-go-lucky place to a darker place was really easy. I was surprised by that.

Do you think it was because you were in a good place that you were able to access that more freely and not be afraid of it?

Yes, and I think [my dad] created a safe set so it felt okay to be naked.

I’m assuming you’re going to continue to pursue acting after this. You have to have some kind of love for it to give the performance you did.

I definitely want to pursue it further, and I did have a lot of fun, even though the film is a lot of me crying. But I want to continue doing it for sure.

This interview has been edited and condensed.

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