Dylan Penn, then 18, moved to New York City in order to intern at the Lipman agency’s art department. She chuckles as she recalls how she spent two-and-a-half months looking for rose photos that would be next to Natalie Portman’s face in Miss Dior’s perfume. “And then I realized, ‘I don’t give a damn!’ That’s when I decided, ‘OK, I really want film.’
Penn, the daughter, and son of Robin Wright and Sean Penn, has always imagined herself in the industry, but not on camera. Over the phone, the 30-year old says that she never imagined acting. “I thought it was really silly as an occupation.” But when she got the chance to play opposite her father in Flag Day, she felt different.
Flag Day is based on the book Flim-Flam Man: A True Family History. tells the story of Jennifer Vogel’s turbulent relationship with John, her con-man father. The film follows Jennifer’s Midwestern childhood during the Seventies. There, the family dances to Bob Seger’s “Night Moves”, before John sets fire to their house to pay off a debt. He is then wanted for counterfeiting $20,000,000. She struggles to break the ties between them, from her rebellious teens to her career as an investigative journalist.
When Penn was 15 years old, her father gave her Flim-Flam Man. He encouraged her to portray the role of Jennifer. But she declined and continued to be hesitant about taking on an acting role. Penn was able to relate to the role because she felt that she had enough life experience to be able to read the script again years later.
She says that she saw many parallels in her life. “The most important thing for me was the need to let go of her parents’ past and to forge her own path as a true truth-seeker and journalist. Because I have never felt independent, I can identify with this sentiment. I wanted to work in this industry and not just be ‘the ….'” daughter’.
John Vogel was portrayed by several actors, including Casey Affleck who dropped out because of scheduling conflicts. Sean was cast 28 days before filming began — it was his first film in which he starred or directed. Penn was reluctant to be directed by her father, let alone act with him.
She says, “He’s amazing as a director because he understands what it’s like being in your shoes.” He would pick me up even if I fell a million times. Although he is my dad, I felt like we were in a professional relationship. He held my hand all the time. He’s an actor and a great actor. He gave me so many things to react to.”
Jennifer, who is interviewing at a diner and then seeing her father being chased by police officers is one of the most moving scenes in the film. Penn had not seen any news footage before filming the scene. She says, “I just saw my father.” “It was really meta. My dad was actually crying behind my camera, watching as I cried.”
Penn’s brother Hopper appears on screen as her sibling, creating a family dynamic she likens to group therapy. She laughs, “I’m crying most of the frames in this movie.” Eddie and Olivia Vedder, a father-daughter team, also contributed music to the film alongside Cat Power and Glen Hansard. She says that it’s crazy because she has known Olivia since she was a child. “Obviously they were there a lot when my father was working on Into The Wild with Eddie. She is her father as a woman, so deeply and so present.
Penn describes her childhood in Marin County California, as idyllic. It was a place she called “granola rich hippie,” where she spent most her time riding bikes around Phoenix Lake with her friends. She was often asked about her Bob Dylan fan status. She says, “It took me long because it was always brought up.” He’s a poet. His music is something I respect.”
Penn mentions her brother who introduced her to Jackass and stoner comedy. It’s difficult not to wonder about Jeff Spicoli, the elephant in the room. Penn was 13 when her family had Fast Times in their library. She says, “It was the age when everyone is trying new things and all the boys were like: “Dude, your father is such a stoner in this movie.” It’s a great movie. It’s the perfect high school movie.
After her stint in New York, Penn moved to Los Angeles to study film at the University of Southern California. She says that her parents were basically like “You’re cut off, if you don’t go to school,” she said. “So I would work as a model and deliver pizza at night. I would wear full hair and make-up to deliver pizza to frat houses. I was misinterpreted as a stripper many times.”
Penn was a screenwriter through her godmother Erin Dignam. She never revealed her last name and edited screenplays as an extra gig. She told her parents she wanted to produce and direct, but they suggested that she start acting. She says that her parents, on two separate occasions, said she should not attempt to direct anything unless she has experience acting. “That was why I originally took my first job.”
Penn starred in Condemned (2015), a horror-comedy. She also made an appearance in Elvis & Nixon. Flag Day is her first major role. She’s determined to direct, but Dylan isn’t quite done acting. She says, “I would love to do, like a dark comedy.” That would be great. It was because I was very close to Jennifer, it would be great to do something outlandish. I am interested in doing something completely different from what I do.
It all seems blurred, between the attention she gets and the amount of media coverage she has received. Dylan laughs and admits that she has never worked so hard. It’s been a difficult learning curve.