Dylan Frances Penn — the daughter of Hollywood heavyweights Robin Wright and Sean Penn — is often referred to as an "It girl" in the press. Fans of Penn probably aren’t surprised by this description given that she’s a beautiful and talented kid of Hollywood royalty. Penn, however, isn’t completely sold on this moniker. Although Penn thinks the term is a flattering one, she knows there’s more to her than her cool girl attitude and famous last name. In fact, there are a lot of surprising details most fans don’t know about Penn’s life. For instance, many would be surprised to learn that Penn once worked as a pizza delivery girl, a job that she held during her college days. Yep, Penn was once a college student. That’s pretty unusual consider how many celeb kids forgo a four-year education for the limelight.
So what else is Penn hiding up her sleeve? Let’s take a look at the untold truth of Dylan Frances Penn.
She has a big ego
As low-key as Penn might seem on the surface, the truth is she has a sizable ego. Penn’s candid admission came up during a conversation about her dad, the famous actor Sean Penn. "I’ve always said I’m more like my dad," she revealed in an interview with The New York Post. "We both have an ego. We’re both like very opinionated and, I don’t know, sometimes confident in a way that could be annoying." Hey, at least Penn was honest. It can be a bit irritating when famous people feign total humility, right? Plus, it’s kind of sweet that Penn and her dad are so alike.
Although Penn embraced her confidence for years, she wants to be more humble going forward. And interestingly enough, she is working on this positive change alongside her dad. "Both of us have realized recently we need to kind of chill out. He’s taken a little bit longer than me," Penn added. As for why her father decided to revamp his outlook, Penn told the outlet that in "his his old age he’s come to realize it’s just not very attractive anymore." Well, at least he came to this conclusion eventually.
Her hilarious start as a pizza delivery girl
Imagine opening your door one day to find Penn standing there with a pizza in hand. It sounds like an unbelievable scenario, right? Although it might be difficult to fathom, Penn once worked as a pizza delivery girl in a neighborhood near the University of California in Los Angeles (UCLA). If you’re asking why someone born to ridiculously wealthy parents would ever deliver pizzas, the story is an interesting one.
After Penn dropped out of the University of Southern California, her parents gave her a tough financial ultimatum that forced her to consider some less-than-stellar job opportunities. "I dropped out of USC after a semester, and my parents told me I was financially cut off," Penn recalled to the Daily Beast. "So my godfather owns a pizza place in Westwood by UCLA, and offered me a job. And I delivered pizzas."
Of course, Penn’s delivery days were far from glamorous. Not only did Penn receive bad tips (we’re talking about college students here), but she was repeatedly asked if she moonlighted as an exotic dancer. Yep, that happened. "After I was asked if I was a stripper, like, three times, I was like, ‘I’m done,’" Penn recalled.
The good news is Penn walked away with something valuable from her experience — "humility and patience." All’s well that ends well, folks.
She regrets her racy photos
It’s not uncommon for people in the entertainment industry to have regrets. Want proof? Look no further than Penn’s revelation that she wishes she could take back a racy photoshoot she did for Treats magazine. The 2014 photos, which were published when Penn was 22-years-old, feature her in various states of undress. In one particular snap, Penn poses with nothing but a dangling chain necklace.
Although the photos got a mostly positive response, Penn doesn’t look back on the bold decision fondly. "To be honest, if I could go back, I would not have taken that much clothing off," Penn admitted a few months after the shoot (via E! News). "I was a little naive."
Call us crazy, but we think her parents’ reactions to the photos might have something to do with the regret. Apparently, they were not happy about the spread. What made matters even worse was that Penn didn’t give them a heads up before the photos were published — talk about an awkward situation! "They were a bit surprised because I didn’t warn them," Penn revealed (via E! News). "And my dad said, ‘OK, you reached the limit. You better not go any further.’ I learned my lesson."
Unfortunately for her parents, Penn is a legal adult. There’s not much they can do if she decides to strip down in the future. C’est la vie.
She’s a huge fan of Charlize Theron
Following their acrimonious divorce in July 2010, Dylan Francis Penn’s parents went on to date other people. Although it can be difficult for kids to see their parents moving on, Penn handled the situation pretty well. In fact, Penn truly adored Sean’s ex-fiancée actress Charlize Theron. Penn got to spend a lot of time with the couple during their year-and-a-half relationship, and she often sung Theron’s praises to the press. In a conversation with Us Weekly in October 2014, Penn gushed about Theron: "Well, she’s brilliant for one thing … and she’s the only woman since my mom [Wright] who can shut my dad up. The only woman! That is a f***ing challenge so … She’s a powerhouse." Congrats to Theron on her achievement — we don’t doubt Penn’s claim that shutting up her dad can be a difficult task.
But wait — Penn’s love fest for Theron didn’t end there. Following her father’s breakup with Theron, Penn admitted to keeping in touch with her dad’s ex. "She’s the best. She’s hilarious," Penn told Us Weekly in July 2015. "She’s very bold, in the best way." Aww, it sounds like Theron and Penn really bonded.
She doesn’t understand social media
Many young celebrities are on social media 24/7. Whether it be for marketing purposes (think Kylie Jenner plugging her makeup line) or brand development, most famous twenty-somethings are adept at using social media to their advantage. When it comes to Penn, however, she has a lukewarm relationship with social platforms. Although Penn has both private and public Instagram accounts, she doesn’t buy into the whole sexy selfie thing. Go figure.
"The whole ‘selfie’ thing is not really my vibe I guess," Penn admitted, according to Vogue Australia. "I’m a very private person and I feel like I’m already starting in an industry that’s very public so anything I can keep special or private, to myself, is something that I find is very precious." That’s not all, though. Penn also implied that people who take selfies all the time are a bit strange. "It’s such a part of our culture now," Penn said about the selfie craze. "There’s no shame in getting your camera out and getting your perfect angle. It’s bizarre to me." To each their own, we guess.
She never dated Robert Pattinson
One of the more interesting rumors about Penn’s life is that she once dated Twilight actor Robert Pattinson. Gossip about Penn and Pattinson reached a climax in September 2013 after the two were supposedly spotted at a concert together in Los Angeles. And just a few weeks after the rumored sighting, a source connected to Pattinson told People, "They’ve been dating a month or two. He’s crazy about her."
As any entertainment aficionado knows, however, most celebrity dating rumors often add up to nothing. Just because a celebrity is hanging out with another celebrity, they’re not automatically romantically linked. So, was this the case for Penn and Pattinson? Apparently so. "We’re just friends," Penn said about the relationship gossip in September 2014 (via Hello! magazine). "They photographed us in a place where there were other people and cropped the picture. Silly. I laughed about it."
Hey, at least Penn had a good chuckle about the story.
Her dad’s alleged fight with her ex-boyfriend
It’s never fun to have your love interest and your parent at odds — especially when it plays out in the public eye. Unfortunately, this is a situation Penn had to deal with when her father and mother met up with her then-boyfriend, musician Jimmy Giannopoulos, for dinner in Brooklyn, New York. After the group finished their meal, the paparazzi photographed Sean yelling at Giannopoulos as an exasperated Wright looked on. Although it’s not clear what the trio had been talking about, the conversation became especially tense after Sean shoved a cell phone screen in Giannopoulos’ face. "Sean had his cell phone in his hand and held it up to Jimmy’s face to show him the screen," an eyewitness told Radar Online. "A heated exchange followed, and Sean’s face got redder and redder as he confronted Jimmy with whatever was on the phone." Hmm, we’re dying to know what was on that screen.
Following the heated exchange and a crying spell from Wright, the unlikely group parted ways without further incident. "It wouldn’t have been surprising if things had really gotten out of hand," a source said about the uncomfortable meeting, according to Star magazine. "This confrontation clearly struck close to home and seemed emotionally devastating. Thankfully cooler heads prevailed in the end." Phew, what a relief. We hope whatever happened that day has since been resolved.
She’s happy she didn’t grow up in Los Angeles
It’s extremely common for celebrities to raise their kids in Los Angeles. Other famous parents, however, choose to set up camp outside of the bustling city in hopes that it will keep their kids out of the spotlight. As it turns out, Sean Penn and Robin Wright took this approach with Dylan Frances Penn and her younger brother, Hopper Penn. Instead of raising their kids in Tinseltown, the two actors opted for a low-key area outside of San Francisco — a choice Dylan Frances Penn is thankful for.
"Let’s just say thank god I didn’t grow up in LA. No, in all seriousness though, I was raised outside of San Francisco in Marin County in a small, suburban town called Ross, and I couldn’t have chosen a better, more beautiful place to grow up," she shared about her "normal" upbringing (via Evening Standard). "I don’t deny that I had a very privileged upbringing but my parents and that town maintained a sense of normalcy that I think many people find hard to achieve and I am so grateful for that."
How interesting. One would think that many young teens would love to grow up in a major city!
She’s inspired by her dad’s friendship with Madonna
Throughout the years, many fans have maintained a strong interest in the nature of Madonna and Sean Penn’s lasting friendship. The curiosity makes sense when you consider the two had a very tumultuous marriage that ended in assault allegations against the actor. Understandably, some people don’t understand why the two would remain close when their relationship was incredibly rocky. So, what’s going on here? Are the exes hook-up buddies or something? Or have they buried the hatchet because they value their friendship? As it turns out, the two are just friends. "I think he just really admires her work," Dylan Frances Penn said about her father’s connection to Madonna, according to Entertainment Tonight."They’re just really good friends and [I think] it’s sweet that they can have this relationship."
As for how the celebs’ friendship affects Penn on a deeper level, she said she’s inspired by their camaraderie. Essentially, Penn hopes to model her own relationships after their strong connection. "They are close friends and so cool with each other. It’s nice to see that respect still remains and there is still love for each other there," Penn told FOX411. "It makes me happy. It makes me think I can have that with my ex-boyfriends when we are older."
Although some people might find Penn’s admiration odd, you have to admit that her casual acquaintance with Madonna is pretty cool. Who wouldn’t want to hang out with a music icon?
She’s close with both of her famous parents
One of the most endearing things about Penn is her bond with her mother and father. Unlike some celebrity kids who try to distance themselves from their famous parents, Penn often talks about her admiration for hers in the press. In one particular heartwarming incident, Penn gushed about Wright’s work in the Netflix series House of Cards. "I binge watch House of Cards compulsively, and I think it’s the first time I’ve ever seen one of my mom’s projects and totally forgot she was my mom," Penn told Elle. "She’s honestly that good, and, also, her character is the exact opposite of who she is in real life."
Additionally, Penn isn’t afraid to talk about her parents’ influence on her own acting career. "I think the one piece of general advice that they gave was just to never do something that felt off," Dylan revealed, according to Entertainment Tonight. "Never do something that felt false for me or else that’s going to show up on screen. Which really helped me in the end."
But the most adorable aspect of Penn’s relationship with her parents is that she frequently shows up at their red carpet events. From Penn’s arrival on the 2016 Cannes Film Festival red carpet with her dad to her appearance at the 2017 Primetime Emmy Awards with her mom, she’s clearly her parents’ biggest fan.
Her brother struggles with addiction issues
Addiction is a disease that doesn’t discriminate. Any person — regardless of wealth or status — can be touched by it. One person who knows this reality all too well is Dylan Frances Penn and her brother, Hopper.
Sadly, Hopper suffered from a crystal meth addiction that landed him in the hospital. "I was pretty bad," Hopper said about his tough times in an interview with Evening Standard magazine. "I just got caught a lot doing stuff, you know?" Luckily, Hopper decided to go to rehab after his father delivered him a stern ultimatum. "I went to rehab because I woke up in a hospital and my dad was like, ‘Rehab? Or bus bench?’" Hopper recalled. "I was like, ‘I’ll take the bed. Thank God I got out of that because that was the worst time in my life."
Although Hopper completed rehab, he was arrested in April 2018 on drug possession charges. Hopper and his actress girlfriend, Uma Von Wittkamp, were driving on an interstate in Nebraska when a Nebraska State Patrol trooper pulled the couple over for allegedly failing to signal. When the trooper searched the vehicle, he discovered 14 grams of marijuana, four amphetamine pills, and 3 grams of psilocybin (mushrooms). Hopper was then charged with possession of a controlled substance and possession of marijuana.
As for how Penn is handling Hopper’s issues, one can imagine it hasn’t been easy for her.