“I really did think that acting was the most ridiculous career choice: dressing up as a different character as an adult,” says Dylan Penn, seated on a striped sofa in the lobby of The Greenwich Hotel, a quilted Chanel bag resting beside her and a large bottle of water between her hands.
The 30-year-old daughter of Robin Wright and Sean Penn is in New York for promotion of her first major leading film role, after premiering the movie at Cannes and with screenings last week in L.A. She’s a long way from her childhood stance on acting — and what an entry into the industry it is. Penn is the lead role of “Flag Day,” directed by her father and co-starring both her father and her brother, Hopper, in the based-on-a-true-story tale of Jennifer Vogel’s life with a secret con man as a father.
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“Flag Day,” released today, is based on Vogel’s memoir “Flim-Flam Man,” about her life growing up in Minnesota with a father who turned out to be a notorious counterfeiter. Vogel has spent 20 years trying to get it made into a movie; Sean Penn has had the option for the script for 15 of those years, and has wanted his daughter to take on the role of Jennifer ever since.
“He originally asked me when I was 15 to do it with him. I said no. Never thought I would act in a million years,” Penn says.
Fifteen years later he again pitched the movie to Penn, though this time he wasn’t planning to play the role of her character’s father but just direct. As it happened, a last-minute change meant the original actor had to drop out, and he was stuck looking for his John Vogel.
“My dad went to I think seven different actors, from Brad Pitt to Michael Fassbender. And then I think Matt Damon was the one that told him, ‘You’re crazy, you should do this,’” Penn says.
As it turned out, working alongside family was the best thing she could’ve asked for — both for the job, and for their father-daughter relationship, to see her dad in that way.
“He’s really casual about it and really human about [directing]. Nothing is technical about the way he prepares,” Penn says. “Being that vulnerable in front of a crew that you don’t know, in the beginning, is something that I thought would be really difficult for me. And instead it was really cathartic. And I think to do it with my family, it was almost being in family therapy because even though it’s not us, there are parallels that I can draw.”
Growing up, Penn was always interested in writing and directing, and though she didn’t seek her parents’ advice on getting into acting, they both knew that ultimately that was an experience she’d need to have.
“I’d expressed that I wanted to direct, at 18, to my parents. And they both, separately, on different occasions, said basically, ‘You should not step foot on a set, as a director, unless you know what it’s like to act.’ It makes so much sense when you think about it. To direct actors you should know what it’s like to be in their shoes,” Penn says. “That’s originally why I started auditioning.”
Their upbringings are certainly dissimilar, yet Penn related to Vogel’s struggle of building a life out from under your parents’ shadow.
“This idea of finding your own identity without your parents’ brand on you. It’s funny because it’s like, I’m in this business. I just did a movie with my dad. I’m Sean’s daughter. But when I was younger, especially just getting out of the house, I felt like I didn’t want that attachment,” Penn says. “I don’t want to just be, ‘The daughter of.’ Especially because I wanted to be in this industry. Jennifer, her past was always going to be a part of her. It’s wanting your own identity, but accepting that that’s a piece of you.”
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