When Dylan Penn was 18, she moved to New York City and began interning in the art department of the Lipman ad agency. “I spent two-and-a-half months sourcing photos of roses that would go next to Natalie Portman’s face for Miss Dior perfume,” she recalls with a laugh. “And I realized, ‘I don’t give a fuck!’ That’s when I decided, ‘OK, I really want to do film.’”
Penn, the daughter of Sean Penn and Robin Wright, always pictured herself in the industry — just not on camera. “I never thought in a million years that I wanted to act,” the 30-year-old says, over the phone from a hotel room in Los Angeles. “I thought it was actually really silly as a profession.” But when the opportunity to star opposite her father in Flag Day came around, she felt differently: “It felt like too good of a role to pass up.”
Flag Day, based off the book Flim-Flam Man: A True Family History, tells the story of Jennifer Vogel and her tumultuous relationship with her con man father, John. The film moves from Jennifer’s Midwestern childhood in the Seventies — where the family dances around to Bob Seger’s “Night Moves” before John burns down their home to escape owing money — to the Nineties, when he’s wanted for counterfeiting $20 million. Through her rebellious teenage years to her career as an investigative reporter, she grapples with their bond, struggling to sever ties.
Penn’s father gave her a copy of Flim-Flam Man when she was 15, encouraging her to play the role of a young Jennifer, but she declined, still hesitant to take on an acting role. Years later, the script came back around, and Penn felt she had gained enough “life experience” to relate to the role.
“I had a lot of parallels to her life,” she says. “The biggest thing for me was this need to detach from her past and her parents and forge her own way into being a real truth seeker as a journalist. I identify with that, because I never really felt like I was my own independent self. I wanted to be in this industry, and I didn’t want to just be ‘the daughter of….’”
Several actors were considered for the role of John Vogel, including Casey Affleck, who dropped out due to scheduling conflicts. Sean took the part 28 days prior to filming — his first time starring and directing in a film. Penn was hesitant to be directed by her dad, let alone acting with him.
“As a director, he’s really incredible because he knows what it’s like to be in your shoes,” she says. “I could fall on my face a million times, and he would be right there to pick me back up. I know that’s also the fact that he’s my dad, but I really did feel like I was in a professional relationship. He was holding my hand throughout. And then as an actor, he’s a powerhouse. He gave me so much to react to.”
One of the most emotional scenes in the film is where Jennifer is conducting an interview at a diner, only to look up to the news on the television and see her father in a police chase. The scene was shot live, so Penn hadn’t seen the news footage prior to filming. “I really just saw my dad,” she says. “It was really meta, but my dad was actually crying behind the camera, watching me cry.”
Penn’s brother Hopper also appears as her sibling on screen, creating a family dynamic that she likened to group therapy. “I’m crying in most of the frames of this movie,” she laughs. Another father-daughter duo — Eddie and Olivia Vedder — also worked on the film, contributing music alongside Glen Hansard and Cat Power. “It’s so crazy, because I’ve known Olivia since she was a baby,” she says, “and obviously they were around a lot when my dad was working on Into the Wild with Eddie. She is her dad as a woman, so deep and so present.”
Penn describes her childhood in Marin County, California as idyllic, a “granola rich hippie” place where she spent most of her time outside, riding bicycles around Phoenix Lake with friends. Named after Bob Dylan, she was often asked if she was a fan. “It took me a long time because it was always brought up,” she says. “But he’s a poet. I definitely respect his music.”
When Penn mentions that her brother introduced her to Jackass and stoner comedies, it’s hard not to ask about the elephant in the room that is Jeff Spicoli. The family owned Fast Times at Ridgemont High in their library, so Penn watched it when she was 13. “It really that age where everyone is experimenting and all the boys were like, ‘Dude, your dad is such a stoner in the movie,” she says. “I love it. It’s the quintessential high school movie.”
Following her stint New York — balancing Lipman’s and waitressing at a restaurant to pay rent — Penn moved to Los Angeles, studying film at University of Southern California before dropping out. “My parents were basically like, ‘You’re cut off if you’re not going to school,’” she says. “So I would model by day, deliver pizza by night. I would come in full hair and makeup to deliver to like, frat houses, so I got misconstrued as a stripper countless times.”
Through her godmother Erin Dignam, Penn edited screenplays as a side gig, never revealing her last name. When she told her parents about her desire to direct and produce, they suggested she try acting first. “Both of them on separate occasions said, ‘You should not try to direct something unless you know what it’s like to act, because you would be a horrible director for actors,’” she says. “That’s originally why I took my first job.”
Penn starred in the 2015 horror comedy film Condemned and had an appearance in Elvis & Nixon, but Flag Day marks her first major role. And though she’s still intent on directing, Dylan’s not quite done with acting yet. “I would really love to do, like, a dark comedy,” she says.” I think that would be really fun. Because I felt very close to Jennifer as a character, so it’d be nice to do something that’s just really out there. I’m really interested in doing something that has nothing to do with me.”
But between being in the spotlight and the amount of press she’s done, it all feels like a blur. “I’ve never worked that much,” Dylan admits, laughing. “It’s been a tough learning curve.”