Julia Stiles, lips glazed mauve, eyes iced blue, is 17 and starring in a movie called 10 Things I Hate About You, a rom-com based on Shakespeare's The Taming of the Shrew, set to the music of Letters to Cleo. It would be a moderate financial success, failing to crack the top 50 highest-grossing films that year, but would eventually become a cultural touchstone. To call it a cult classic would be not only reductive but also incorrect — cults are tiny groups with niche interests; 10 Things is a canonical coming-of-age film, and one that has held up remarkably well over the decades.
2019: Julia Stiles endures interview after interview, at least one with a reporter who is shoveling hummus into his mouth at a desperate pace, about an experience she had for a few months 20 years ago.
"Did you realize it was going to be such a hit?" I ask. "No, I didn't," she says. "And the minute you start thinking that, then it's over." When I ask if she's tired of talking about it, she doesn't smile so much as press her lips together: "No, it's nice when people say that they remember it and that they like it. If I weren't working now, maybe I would be like, 'Hey, can I move on from that?' But I'm happy."
If 10 Things were to be reshot tomorrow, Stiles could swan-dive back into a pair of low-rise jeans and we the people would be none the wiser. The only thing that has changed about her face between now and 1999 is our language to describe it: Her skin no longer shimmers; it glows. Her highlights are no longer chunky, but balayaged in the downtown tradition.
In 1999, Stiles was selected to play the platonic ideal of an American teenager — the intelligent weirdo who is inexplicably gorgeous. Today, she is the platonic ideal of the brownstone-Brooklyn mom, discussing her favorite David Foster Wallace descriptor (“bovine”) and carrying a flimsy but sort of insouciant cotton shopper to and from press appointments. (She asks me to describe it as a Birkin bag in the text, which I will do!)
And her career has weathered two decades of zeitgeists. This fall, she stars with Constance Wu and Cardi B in Hustlers, based on the New York magazine story by Jessica Pressler about a group of exotic dancers and other strip club workers accused of drugging and robbing some of their male patrons in 2013. The film capitalizes on American culture's obsession with female grifters (sparked by Elizabeth Holmes's Theranos).
Stiles mentions that before she knew about Hustlers, she became aware of Pressler through her New York story about Anna Delvey, a SoHo impostor who siphoned off the trust funds of acquaintances to pay for an exorbitant lifestyle and nascent art business. When multimillionaires, especially the ones who seek public office, have emerged as the decade’s most reviled villains, grifter stories aren’t just entertaining — stories like Delvey's are also improbably heroic.
It is not hard to be nostalgic for two decades ago, when the Internet was less of a thing, when our nation's best defense against the sinister forces of capitalism was more than just a merry band of strippers. Unless you're Julia Stiles, who is hardly nostalgic at all.
It is unfortunate for her, then, that just the day before she was asked to revisit the defining beauty looks of the '90s — barrettes, brick red lips, baby blue eye shadow — they, somewhat improbably, resurfaced to haunt her.
"Why are these trends coming back?" she asks either me or God. "I feel like I blocked out so much of the '90s. I don't know why. It was high school [for me]. That's why. There was good music. And I’m glad my eyebrows came back."
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Later, Stiles picks up her Birkin bag, made of the most expensive animal hide available, in a color that is both eye-catching and goes with everything, and leaves the restaurant, returning to 2019.
Fashion stylist, Ye Young Kim. Hair: Rita Marmor. Makeup: Courtney Perkins. Manicure: Geraldine Holford.
A version of this article originally appeared in the October 2019 issue of Allure. To get your copy, head to newsstands or subscribe now.
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