Dylan Penn welcomes guests high above the Croisette, in a sterile penthouse suite overlooking the ocean. It’s a place befitting of her status as a visiting Hollywood royal, daughter of Sean Penn and Robin Wright, starring alongside her father in this year’s Cannes competition. He’s got a phone and water and a stylist on the wing. He’s been here all day and won’t come down until dusk. He had tickets to see Wes Anderson’s new film.
In fact-based Flag Day, her first leading role, she played Jennifer Vogel, the daughter of a common conman. John Vogel describes himself as a businessman with an extensive portfolio, which is another way of saying he was a bank robber, arsonist and forger; always up to no good, constantly looking over his shoulder. Jennifer wanted to break free but couldn’t cut the cord. “In my dreams, my father has always been a prince,” he explained.
Flag Day was officiated at the festival to highly esteemed reviews. But it’s a film that comes with a built-in honking irony: the story of a woman who succeeds despite her father starring a woman who plays — at least in part — because of hers. Penn Sr directed, played John and said he couldn’t imagine anyone other than Dylan as Jennifer. His daughter, on the other hand, was not at all convinced.
“Oh yes, very doubtful,” he said. “I don’t know if I can come face to face with my father. So it’s always scary – the energy in the room is with him both directing and acting. Because I was very affected by his presence and it was difficult for me to relieve his stress.” He shrugged. “Also I feel he might be arrogant as a director and force his choices on me, leaving me no room. But I couldn’t have been more wrong. We complement each other pretty well, I think.”
Having famous parents definitely helps in business. But it also provides a pressure, feeling of a high bar to go through. “Sometimes I audition and because of my last name there is an added expectation. It can intimidate and hold me back.” another shrugged. “But yeah, in the end, I think that’s an advantage.”
He is named after Bob Dylan, the singer he comes around now that he is older, and has a younger brother, Hopper, named primarily for Dennis but also because he was constantly jumping around in the womb. He explained that the family grew up mostly in Marin County, outside of San Francisco, far from LA. “Very outdoor. Very granola. Basically, it’s full of rich hippies. ”
Penn wasn’t astute enough: she turned 30 this year and worked as a model before returning to film. He took on the lead role of Cursed, the obscure 2015 slasher film described by the Hollywood Reporter as “one of the most horrific horror films ever to come to recent memory” and played a concierge in Elvis and Nixon, alongside Michael Shannon and Kevin Spacey. He liked Gus Van Sant, Greta Gerwig and especially Woody Allen. He says Annie Hall is his favorite movie of all time. One day, ideally, he would like to write and direct his own work.
I don’t think she has the bad luck to compete with Jennifer Vogel, who toyed with poor parents in blue-collar Minnesota and lived a rough life as a teenager before training as a journalist. The closest he got to it was the few years after high school, when he drifted outside of the family orbit and lived on his own dime. “I left home at 18 and didn’t go to college right away,” he recalls. “And my parents were like, ‘Well, we’re not going to pay you for just messing around.’”
During this time Penn worked as a waitress and barista and spent six months as a pizza delivery driver. Sometimes, she said, she was mistaken for a stripper. “Well, what happened was that I started doing test shoots for modeling while working as a pizza delivery guy. So I’d come from a test to deliver pizza with a full face of makeup on and people used to think it was a costume and that they were going to get more than just pizza.”
The hours are awkward. The pay is terrible. But he now looks back on his work with something close to nostalgia. “It’s like a competition. You race against other racers to see who can get the pizza out and get a tip. His gaze leapt to the large and Mediterranean picture window below. “I like it,” he said. “It was a different world.”