The Evolution of Julia Stiles

In 2019, everything is making a comeback, from bubble skirts to French manicures to bellbottoms. And it’s not just fashion trends. Classic animated Disney movies are becoming live-action box office hits. Beloved TV shows like Full House and Gossip Girl are getting the reboot treatment. Even How to Lose a Guy in 10 Days is being reborn as a series.

While the enticing pull of nostalgia seems extra-powerful right now, it’s more like a constant force, and perhaps no one feels it quite as acutely as Julia Stiles.

Despite having a steady, varied career in the years since her debut in the TV series Ghostwriter, Stiles is perhaps best known for iconic roles that are now steeped in our wistfulness for the late-90s/early-2000s era when she made her name. To some fans, she will always be Katarina Stratford from 10 Things I Hate About You, which came out in 1999, or the pre-med student who falls in love with royalty in The Prince and Me. It's two decades later, and she's still being tagged in 10 Things memes on Instagram. Even so, she’s gracious enough not to mind that we’re all so stuck on her past.

“I am really grateful for that experience, and I don't take it for granted that people still care about a movie that came out 20 years ago,” she says. “I see it as a positive thing.”

When 10 Things came out, a remake in its own right loosely based on Shakespeare’s Taming of the Shrew, it was a part of the heydey of teen romantic comedies, along with She’s All That, and Never Been Kissed. But it stood apart from them even then. As Katarina Stratford, Stiles was a rom-com heroine decidedly different from the ones we were used to seeing. The protagonist in 10 Things didn’t have to undergo a makeover to be deemed worthy of love, and she didn’t spend the movie pining after a boy — something that jumped out at Stiles when she first got the script.

“The reason that I wanted that part so badly was because I thought it was so refreshing, seeing a teenage girl be feisty and opinionated and be a fish out of water, but proudly [so],” she says. “I think that I probably wasn't alone, and that's what other girls and women responded to, and the movie had a real bite to it.”

For a generation of women, Kat was, and still is, a feminist hero. She’s witty, independent, feels no need to impress boys (or anyone else, for that matter), and reads The Bell Jar after school for fun.

But in the years since 10 Things was released, Stiles has carved out a career far beyond the role we fell in love with. In 2001, she pulled off the decidedly un-Hollywood move of enrolling at Columbia University and eventually graduating with an English degree. Perhaps even more impressively, Stiles worked steadily through that time, starring in The Bourne Identity, Mona Lisa Smile, and The Prince and Me all while completing her degree. In fact, she’s been actively working since she got her start as a child actress — a glance over her filmography shows nary a break since 1993. After graduating from Columbia, she continued to star in the Bourne franchise; she took the lead in The Omen, a role in Silver Linings Playbook, and had guest spots on Dexter and The Mindy Project.

Since 2017, she’s been leading Riviera, the Sundance Now show on which she stars as Georgina Clios, the art curator whose world is turned upside-down when her husband is killed in a yacht explosion. The show has just aired its second season, and within a few weeks, she will be back in Europe to shoot the third. As Georgina, Stiles embodies an anti-hero who was first pitched to her as a “female Michael Corleone.”

“I held them to that,” Stiles says. “I was like, ‘I do not want her to be the good girl for the whole show because I'm not interested in that.’ In script meetings, I'm always like, ‘Yeah, I'm not interested in if she's likable or not.’ I mean, I want the audience to stick with her and understand her, but I'm not interested in seeing people make the right decisions all the time, you know?”

Michael Corleone, the Godfather trilogy’s anti-hero, goes from being a decorated war hero to a crime boss who organizes brutal slaughter, all in the name of family and loyalty. The character, played by Al Pacino in 1972, cuts a challenging figure for Stiles to use as fodder for hers.

“We judge female characters a lot more harshly, and if you have a female character doing something questionable, immoral, illegal, or unlikable, I find that storytellers have to jump through hoops to explain why she did that,” she says. “If a male character's running around with a gun, it's cool, but if a woman is doing it, we have to have seen her suffer some horrible tragedy in order to justify it.”

Stiles has been examining the concept of likeability since at least 10 Things. After all, Kat Stratford, described by classmates as a ??heinous bitch,” merely curves her lips into a smirk in response, though Stiles is far from the rough-around-the-edges teen character she’s long been associated with. For one, she’s an adult now. And the grumpy aloofness she portrayed as a teen has been swapped for an easygoing, comfortable confidence that’s almost always accrued with age. On the set of our photo shoot, she kicked off her sky-high stilettos halfway through, and joked with the photographer about her angles: “As long as I only have one chin in this shot, it’s fine.”

At 38, with over 50 film and TV credits behind her, Stiles has seen the culture of Hollywood shift for women. And while we’ve been busy reminiscing on the nostalgia of her early-aughts roles, she’s only looking toward the future.

“In my 20s, I might have been worried about anticipating being an actress approaching 40,” she admits. “I wouldn't know where my career was going to go or if there would be opportunities for me beyond an ingenue or a girlfriend role. Now I think that I'm really excited about the opportunities that are out there for me and my peers, and I think the roles that we're playing have gotten so much more interesting than what we were doing in our 20s.”

Take, for example, Hustlers, the upcoming film based on the 2015 New York magazine story, “The Hustlers at Score,” about a crew of former strip-club employees who con their Wall Street clients out of money. The highly anticipated movie has generated so much buzz that its release date was moved up from its 2020 slate to September 13 of this year.

“That's a story that could have been told many, many different ways,” Stiles says of the Lorene Scafaria-directed flick. “It could have been a true-crime story about the victimization of men. But instead it was very much a perspective of focusing on the sisterhood of these women and how they work together.”

With a stacked cast including Stiles, Jennifer Lopez, Constance Wu, Cardi B, Lili Reinhart, Keke Palmer, and Lizzo, the vibe onset was energetic — something Stiles attributes to Lopez, whom she says she was “floored by” during filming.

“She's very, very disciplined,” Stiles says about J.Lo. “She was handed a full-page monologue my first day shooting with her and she just read it a few times, closed her eyes, and then opened them and was like, ‘Okay, let's go.’”

Lopez wasn’t the only appealing aspect of the project. Stiles was so excited by the script when she first got it that she told Scafaria she’d do anything to be a part of the movie. “I didn't care if I had to make sandwiches for everybody or sweep the floors.”

Thankfully for us, the team behind Hustlers opted to use Stiles’ talents in front of the camera, as Elizabeth, the journalist who investigates the women involved, becoming the audience’s eyes and ears into the Hustlers’ world. It's a film that never would've been made in the '90s or early-2000, Stiles says; or if it had, it would have demonized the women in it, treated them as despicable people, or shown them being brutalized in some way out of the belief that an audience couldn’t possibly sympathize with strippers unless we saw them suffer some major tragedy to justify their con.

“I know that the director tried to get that movie made and a lot of studios turned it down and said, ‘No, we can't touch this material,’ until finally they got Jennifer Lopez involved, and then it was off and running and got green-lit,” she says. “That, I think, is due to the cultural shift because of #MeToo.”

With all the opportunities opening up in the wake of Hollywood’s shift, Stiles is also excited to hone her skills behind the camera as a director. “I have had great opportunities as an actress and in life, but I directed a couple of shorts, and I think I'm ready to try something longer,” she says.

It may be a while, she says, until her busy schedule as a working actor and parent calms down a little. She and husband Preston J. Cook welcomed their son, Strummer, in 2017. And though she’s excited about being a mom, she’s private about that part of her life, after she posted a photo of her baby on Instagram in 2017 and her comments were flooded with criticism of how she was holding him. Stiles responded to the backlash in a way that would make Kat Stratford proud (telling haters to get off Instagram and "try dancing around your living room to a Clash record"), but a line had been crossed.

“I can take all the criticism, I can deal with that. I'm an adult,” she says. “But when they started making comments about him, the mama bear kicked in and I was like, ‘Oh, hell no. That's totally off limits, and how dare you?’ I don't really have regrets, but it was a big lesson for me to not share photos with my son.”

Having made a name for herself before social media took hold, Stiles says she’s glad she isn’t becoming famous now, when actors are expected to promote themselves online.

“When I was starting out, becoming more successful and having to promote what I was in, doing an interview like this for instance, I'd still be careful about what I was saying, but I didn't have to worry about something being pulled out of context for clickbait and the Twittersphere,” she says.

Adapting to Hollywood in 2019 hasn’t been without its difficulties, but Stiles makes it look seamless. While nestling into our hearts as a forever teen-rom-com icon, she also established herself as one of the most versatile and hard-working actors out there, going toe-to-toe with Matt Damon in the action-packed Bourne films, giving Shakespeare a modern, cool twist in O and Hamlet, and deftly grappling with grief and murder in Riviera.

Is there anything she hasn’t done that would be on her radar?

“A comedy would be nice,” she says drolly. “When I'm on the set of Riviera and I'm having to cry and scream all the time, I'm like, ‘Note to self: Try to do some more comedy.’”

Photographs by Kyle Dorosz, assisted by James Marquis. Lisa Aharon using Chanel at The Wall Group. Nate Rosenkranz for KMS Hair Care at Honey Artists. Art direction and production by Kelly Chiello.