Winona Ryder (né Horowitz) lives with her family in San Francisco but briefly resides in Colombia at the home of Chilean revolutionists, who were friends of her parents. When Ryder is 7, the clan settles down at a 300-acre commune in Mendocino, Calif. – where beat poet Allen Ginsburg and outspoken psychedelic-drug guru Timothy Leary befriend her parents. Ryder "was an unconventional child," her father Michael tells Newsday in 1993. "She had a flair for style at a young age. And creativity."
Seeking an extra-curricular activity for their loner 11-year-old, who is mistaken for an effeminate male by her classmates, Ryder's parents, Michael and Cynthia, send her to San Francisco's American Conservatory Theatre. Ryder instantly proves to be a natural, eventually catching the eye of a talent scout who sends her to screen-test for a role in Desert Bloom. Although Ryder isn't cast, the screen test leads to her feature debut in Lucas (right).
Director Tim Burton casts Ryder as an outcast, death-obsessed teen in Beetlejuice (left), with Michael Keaton. The quirky film grosses almost $73 million. "I've gone through very dark stages where I would only wear black [as did her character]," she tells the Los Angeles Times. "I went through that stage right before I did that movie, so it was a cinch. I was very dramatic; I was like a living sigh."
The L.A. Times declares that Ryder is "Hollywood's hottest young heartthrob, heiress apparent to Molly Ringwald's teen throne" when she stars in the dark teen film Heathers (right). The movie quickly achieves cult-hit status with Ryder as teen murderess Veronica Sawyer. "As soon as we saw her onscreen, everybody immediately said: 'That girl is a movie star,'" director Michael Lehmann tells Los Angeles Magazine. Ryder confesses of her luck, "I never had to do the Hollywood thing, to move to L.A. and do commercials or sitcoms. That probably pisses people off. But I've worked really hard. I'm not going to apologize for not struggling."
Ryder works with director Tim Burton again as the empathetic Kim Boggs in the box-office hit Edward Scissorhands. While filming, Ryder begins dating costar Johnny Depp (left). "There's been nothing in my 27 years that's comparable to the feeling I have with Winona," Depp tells PEOPLE. The two move in together, become engaged in 1990, and Depp famously has "Winona Forever" tattooed on his upper right arm (he'll later alter it to "Wino Forever" after they call it quits after three years).
After dropping out of Francis Ford Coppola's The Godfather: Part III, Ryder checks into a psychiatric hospital after suffering from exhaustion, anxiety and depression. But she leaves the facility in less than two weeks. "I just realized that no matter how much money you pay," Ryder, who appears on a 1991 cover of Rolling Stone, says, "these places don't have the answers. Because there are no answers. You're just a human being, and you make a choice to go on with your life."
Ryder plays May Welland in Martin Scorsese's adaptation of the novel The Age of Innocence (right). "[Ryder] is unafraid of trying to find the truth of a character or situation," Scorsese tells Vogue in 2007. "Add to that her extraordinary range, warmth and humor, and I believe she's truly one of the best actors of her generation." For Innocence, Ryder wins her first Golden Globe Award and nabs her first Academy Award nomination for Best Supporting Actress.
Ryder briefly slips into jeans for Ben Stiller's Reality Bites, but is soon back in hoopskirts as the feisty Jo March in Little Women with Claire Danes (left) and Kirsten Dunst. Ryder earns another Oscar nod, this time as Best Actress. "I related to [Jo's] passion for the arts and her drive and her stubbornness and her frustration," Ryder says.
After appearing on PEOPLE's 50 Most Beautiful list, Ryder nabs her first action-adventure role alongside Sigourney Weaver (right) in Alien Resurrection. "I didn't care if I died in the first scene," Ryder tells the Chicago Sun-Times. "I just wanted to be in an Alien movie. I've seen all of them hundreds of times. I had Sigourney's poster on my wall for 17 years." Afterward, Ryder opts for a two-year hiatus: "I didn't want to work just for the sake of working. I also wanted to have a life outside of just working."
At a New Year's Eve party, Gwyneth Paltrow, who is dating Ben Affleck, introduces Ryder to Affeck's pal Matt Damon. At the time, Damon is dating Minnie Driver, his Good Will Hunting costar, according to Driver, who claims she only learned about their breakup from Damon's Jan. 12 appearance on The Oprah Winfrey Show. Ryder and Damon date until April 2000.
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