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Dylan Penn Doesn't Shy Away From Tough Conversations

by Carrie Wittmer

Dylan Penn
Courtesy of Getty Images.

Dylan Penn never intended to step in front of a camera on a film set. Modeling, writing, and directing felt sensible enough, but growing up, she considered acting a “silly profession,” and specifically did not want to follow in the footsteps of her parents, actors Sean Penn and Robin Wright. After high school, though, Penn began editing scripts and storyboarding with her godmother, a screenwriter. She realized she couldn’t bear the thought of someone else taking over her vision, and so, through learning about the process of filmmaking, she fell in love with writing and directing. But on separate occasions, Penn’s parents told her that if she really wants to direct, she needs to know what it’s like to act first. Now 30, Penn has spent the past several years taking that advice seriously.

I spoke with Penn—a near mirror image of her mother, with the edginess of her dad—over Zoom in the midst of promotion for Flag Day, her first feature film in which she has a starring role. Flag Day, which hits theaters August 20, is directed by her father Sean, who also co-stars with her in the movie, alongside Josh Brolin, Katheryn Winneck, Regina King, and Hopper Penn (her brother). Based on the 2004 memoir Flim-Flam Man: The True Story of My Father’s Counterfeit Life by journalist Jennifer Vogel, Flag Day follows the true story of the tumultuous relationship between Jennifer and her father, the con artist John Vogel. The complex father-daughter dynamic between Jennifer and John guides the story, which spans several decades, from Jennifer’s childhood to her father’s death in her young adulthood, depicting a relationship that would be a daunting emotional experience for any actor to perform on film. In July, Penn attended the Flag Day premiere at Cannes Film Festival. It was a surreal experience for her, as she was there for the first time as a performer, and realized that most of the festival was just a lot of work. “I really imagined going to Cannes and just partying, and having great food, and drinking champagne,” Penn said. “I was in bed at eight every night, so exhausted from working the day.”

Whether romantic or familial, it can sometimes be distracting to watch two actors with a real-life personal relationship perform together on screen. But Penn takes advantage of her real relationship with her father in Flag Day. While the circumstances experienced by the characters are different than in real life, the Penns’ display of emotions feels so strong that the actors practically jump out of the screen. “At the end of the day he's still my dad,” Penn said. “I would say that 80% of the time, I saw my dad rather than John.” She struggled to find the right words to describe the experience of working on the film, not solely because working on the project felt like such a visceral experience, but also because Flag Day filmed in 2019 and wrapped in early 2020, just before the coronavirus pandemic. “It's been funny trying to jog my memory of working with my dad,” she said. “And it feels so distant.”

In nearly every industry, nepotism runs rampant, but the favoring of family is built into the foundation of Hollywood. Every now and then, the Old Hollywood story of a natural, unique talent who moved to Los Angeles with just 20 dollars in their pocket breaks through, but these triumphs occur less frequently the more the industry grows, and more often than not, a rising new talent has some kind of advantage they never want to talk about that helped them get ahead. Most actors who benefit from nepotism might dodge the question or pivot to self-defense mode when they hear the word, but Penn leaned into the camera and admitted straight away: if Sean Penn was not her dad, she probably would not have been cast in Flag Day’s leading role. “I can see being really pissed that I got this role, as someone else,” she said.

Sean Penn and Dylan Penn at the 2021 Cannes Film Festival.

Getty Images

Penn firmly added that although she benefits from nepotism in Hollywood, she has also worked really hard to get where she is today. “'I’ve been auditioning forever. I’ve been rejected forever,” she said. She’s the first to bring up the short film The Rightway, which will star her brother, Hopper, was written by Owen King, the son of horror novelist Stephen King, and will be directed by Destry Spielberg, daughter of Steven Spielberg. “This is the business,” Penn explained. “It is about who you know. Always. Whether you're the son of Sean Penn or not."

Short films rarely make headlines in trade publications, but the celebrity children involved in the project sparked uproar and debate on Twitter about nepotism in Hollywood. (The short film made even more headlines when Ben Stiller, whose father Jerry Stiller paved the way for him to enter the business, defended the industry, calling it a “meritocracy.”) “I don't want to speak for my brother,” Penn said. “[But Destry] wouldn't have picked him if she didn't feel like he was appropriate or talented enough. I guess if you feel like you deserve your place, then yeah, use nepotism.”

Whenever her dream of becoming a director is realized, Penn said she hopes to slow the nepotism cycle by hiring unknown actors from different backgrounds. She wants to work with actors who studied their craft but don’t have agents or any connections in the industry, as well as people “off the street,” something she mentioned her dad has done. The actress has spent the pandemic out of work, but has been auditioning and sending in tapes for roles in addition to working on a concept for a television show with her writing partner that she describes as “Girls meets Requiem for a Dream.” Even with her last name, Penn admitted that she sometimes struggles to get meetings and the right eyes on her work, because she hasn’t directed or written anything that’s been made before. To be hired as a director, you need a reel, and to make a reel you need funding for your films. “My unemployment isn’t going to cover lighting costs,” she said with a laugh.

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