Julia Stiles
Born 1981, she was the teen-Shakespeare queen of the late 90s and early 2000s—flinty and wry where others were bubbly, older-souled than the wave around her. From Kat Stratford's taming to Ophelia to Desdemona to a ballerina's breakthrough, she was the thinking kid's teen-movie star.
Julia Stiles was born March 28, 1981. She broke through on the biggest scale in 1999 as Kat Stratford in 10 Things I Hate About You opposite Heath Ledger, playing the smart, resistant girl who refused to perform femininity for the camera. The role earned her the MTV Movie Award for Breakthrough Female Performance—and positioned her, immediately, as something different from her teen-movie peers. She was flinty. She was wry. She read as older-souled than her years.
She quickly became the era's teen-Shakespeare queen. 10 Things was The Taming of the Shrew; in Michael Almereyda's Hamlet (2000) she played Ophelia opposite Ethan Hawke's prince; and in O (2001) she was Desi Brable—Desdemona in a prep-school Othello. Three Shakespeare adaptations in three years, a run no other star of the wave could match.
Her biggest hit as a lead came on January 12, 2001, when Save the Last Dance opened at #1 with $27.5 million and went on to gross over $131 million worldwide. She played Sara Johnson, an aspiring ballerina rebuilding her life in Chicago, and the film won her MTV Movie Awards for Best Kiss and Best Female Performance. It proved she could carry a hit on her own.
The Bourne Identity (2002) and The Bourne Supremacy (2004) gave her Nicky Parsons, the CIA handler—a supporting role that carried her past the teen era and kept growing with the franchise. In the same stretch she appeared in Mona Lisa Smile (2003) and The Prince and Me (2004). And through all of it she was enrolled at Columbia University, graduating in 2005 with a degree in English literature—the rare teen-wave star who was literally reading the source material between takes. Flinty, wry, and a little older-souled than the movies around her, she remains the era's evidence that a teen-movie breakout could be built on seriousness.
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O
Tim Blake Nelson's modern Othello, relocated to an elite Southern prep school where basketball replaces Venice's wars. Mekhi Phifer as the only Black student and star athlete, Josh Hartnett as the jealous rival, Julia Stiles as Desdemona. It was made to be released in 1999—but held from the world for two years after Columbine.
Freddie Prinze Jr.
Son of the 1970s sitcom legend Freddie Prinze, who died when Freddie Jr. was a baby. He grew up carrying one of television's most poignant legacies—and then became the face of the late-90s teen-movie boom. Dimpled, kind-eyed, and impossibly likable, he was THE heartthrob of an era that believed in nice guys.
10 Things I Hate About You
A witty modernization of Shakespeare's The Taming of the Shrew transplanted to a Seattle-area high school, starring Julia Stiles and Heath Ledger. A modest hit in theaters, it grew into a generational classic and launched the breakout careers of its three young leads.
Adam Sandler
The SNL goofball who became a box-office machine — Billy Madison, Happy Gilmore, The Wedding Singer, The Waterboy. In the '90s his man-child comedies and shouty voices made him one of the most bankable comedians alive.