You’re a UCLA freshman who, ever the world-beater, elects to blow off the “Justice For Kale!” class protest, which many are billing as the social event of the fall season, in favor of an afternoon tryst with the Volcano. Putting on pants just wasn’t in the cards. After hours of Snoopifying, that familiar grumble returns, prompting you to pause Netflix and order a pizza. The strident buzzer sounds, shattering the trance, and you mosey over to the door. It opens. And there, standing before you, is one of the most beautiful women you’ve ever seen.“I did that for about seven months,” laughs Dylan Penn. “I dropped out of USC after a semester, and my parents told me I was financially cut off. So my godfather owns a pizza place in Westwood by UCLA, and offered me a job. And I delivered pizzas.”Now, this wouldn’t seem all that odd if not for the fact that Dylan is the daughter of Sean Penn and Robin Wright, aka Spicoli and Buttercup. And she’s the spitting image of her ageless mother, a woman whose looks are so striking they nearly ignited a war with Russia on the most recent season of House of Cards.
For a while, Dylan resisted joining the family business. After graduating from the competitive Marin Academy, a prep school in Northern California, she moved to New York City in order to pursue her dream of working in an ad agency. She interned at a top-level ad firm specializing in luxury brands, and worked as a hostess at The Breslin to make ends meet. But partway through the internship the job lost its luster.
“It was after the second month of meetings of deciding which rose to use in the Dior perfume campaign, which was going to be set next to Natalie Portman for Miss Dior,” she recalls. “I just didn’t give a fuck, but everyone was so serious about it.”
When the money eventually ran out, she moved back to L.A. and attended USC to study film with the aim of becoming a filmmaker—only to drop out over her frustration with the school’s core curriculum.
In 2013, the name “Dylan Penn” began circulating in the tabloids. She’d landed a few modeling gigs, most notably on billboards for the Gap and a sultry spread in GQ, but really garnered some ink when it was rumored that she was seeing Robert Pattinson following his split from Twilight co-star Kristen Stewart (she’s called it a “bullshit lie,” claiming they’re just friends).
The next year brought more modeling gigs, as well as a spread in Elle slapping her with the beaten-to-death “It Girl” label.
“I never thought I would act,” says Dylan. “It was something I stayed away from my whole childhood, and when I moved back to L.A. I was offered to try out for some parts, but I was never interested because they were all dumb blondes with no arc. But after delivering pizzas for that long and not making any money, a friend of mine suggested I try modeling, which led to the acting thing.”
Why did she stay away from acting? “I’m sure that being the daughter of actors was subconsciously a part of it, but I’m also shy and don’t like to be in front of big crowds,” she says. “It didn’t feel like something that would be good for me, or that I would be good at. And I didn’t like the idea of being vulnerable on camera. But I quickly realized that would be something I could get over.”
Indeed, early on during the filming of Eli Morgan Gesner’s Condemned, a horror flick starring Dylan as a spoiled runaway who shacks up in a run-down Lower East Side building only to see its inhabitants transform into bloodthirsty psychopaths, she shared an intense scene with Johnny Messner—a tough-guy character actor best known for playing a thug named Tommy “Tombs” Perello in the batshit crazy action flick Running Scared.
“He’s a sweet guy, but he kind of scares me—just the way he looks,” says Dylan. “Before we shoot the scene he says, ‘Just go with it. I’m going to surprise you,’ so the cameras roll, and during the scene he suddenly grabs my face and bites the shit out of my lip, and it starts bleeding a little bit. It really hurt. But it was exciting because it was real, and I could react in a genuine way.”
On Day 2 of the 24-day shoot, which required Dylan to appear in nearly every scene, her spread for treats! magazine hit the stands. And the NSFW photos, capturing the aspiring actress in next to nada, caught her by surprise.
“I remember this very clearly because the producer came up to me the day that it came out, and I was really unaware that that photo was going to be used,” she says. “I was actually told that I would have control over what would be published, and I wasn’t informed. So I was shocked and… never again will I do that. Lesson learned.”
Condemned was shot in a semi-abandoned building at 79th Street on the Upper East Side of Manhattan, but the exteriors were captured in the decidedly dicier Brownsville section of Brooklyn, where Mike Tyson grew up. On the final day of filming a street fight broke out, with two women beating each other to a pulp. Police were called, and the set had to shut down temporarily.
Despite all this, Dylan says working on her first feature taught her to overcome her stage fright, and finally accept that, while her ultimate dream is to write and direct her own features, the acting thing can be pretty damn fun.
She’s hoping to film a couple of indies—GenRX and Unfiltered—in the next year, and still gets along great with her very famous parents, both of whom are doing just fine.
“My parents split my senior year of high school,” she says, “and I think because I was older it was much easier, and I was out of the house right after the split, so I wasn’t greatly affected by it. I think it was time for them to part ways, and I think they’re both happier, healthier people because of it.”
While she’s dying to work with her mother, her director-father Sean might be first in line. The two are semi-attached to the film Flag Day, an adaptation of Jennifer Vogel’s memoir Flim-Flam Man.
“My dad’s had this script for a while now and it’s this incredible story,” says Dylan. “It’s about a dad who’s a con artist, and it’s a love story between father and daughter. My dad would be playing the father and I’d be playing the daughter. It’s really intense, and it scares me to think of my dad starring in a film with me and directing me—it’s a lot—and I’m scared of people thinking that I just got the part because my dad is directing it.”
She pauses. “Maybe after I get a couple more films under my belt, I’d do it. I want to earn it.”