The Timeless Appeal of Winona Ryder, Hollywood's Eternal Outsider

"Have you ever confused a dream with life? Or stolen something when you have the cash? Have you ever been blue?" These lines were uttered by Winona Ryder in the 1999 film Girl, Interrupted, in which she played Susanna Kaysen, the writer of the original memoir. No one could have known that they would become uncomfortably prophetic. Troubled with patches of poor mental health, Ryder would go on to spend the best part of 15 years living with the aftermath of a single unfortunate shoplifting event. To some, it tarnished her identity—an identity trapped in our own dreamlike vision of her as she was in the movies.

When Tim Burton picked Ryder to be in Beetlejuice, he didn't know she'd become the cult face of 90s—but he did know that she was special. She'd only been in a couple of movies before, and her presence meant she was a sure bet for the role of Lydia Deetz. Already, she looked like a gothic icon. "A lot of those clothes were my clothes," Ryder told Vogue in 1989. "My skin was actually that pale." Beetlejuice opened in April 1988, and earned $32 million in its first two weeks. The doors had opened for her. Her working relationship with Tim Burton, the master of weirdo pop-macabre, did what it did for other stars and launched her career. Then she made Heathers, an anti-teen movie, in which she plays sort-of popular girl Veronica Sawyer, who kills off the school's queen bee and frames it as suicide.

She might have been wanted for Beetlejuice, but no one wanted her for Heathers. She wanted the part, badly, however. She knew the meanness of teenagers. She'd been bullied, and at her own high school, a goth had been venerated post-suicide by the same people who had terrorized her in life. There was personal meaning in this story for her. Incomprehensibly, she was not deemed sufficiently attractive for the role of Veronica. So she went to Macy's, had a makeover, and, according to Daniel Waters, the screenwriter, threatened to kill herself or them if she didn't get the part.

Dissecting someone's star quality can feel reductive, but never more so with someone like Ryder, whose appeal can defy definition. Why was she so magnetic from the off? Some experts alluded to her "silent movie quality," an ability to captivate just by being, her ability to act without words. When she does talk, it's rich and slightly nasal, distinctive enough to make you do a double take. Her voice is like no one else's. There are, too, her eyes, striking and beautiful and alien-large. She has an otherworldly presence. She's stunning enough to be "popular," but too much of an outsider to ever be. What young person watching her films at the time didn't want to be that girl? She didn't belong, and neither did you.

Watching Ryder in an interview or reading her quotes in a magazine, it's as if she doesn't realize how individualistic she is. But of course, she's utterly cool and intriguingly strange. A quiet rebel. Her upbringing, with counterculture intellectual parents who raised her in a commune in California, probably ignited that streak. They created the Fitz Hugh Ludlow Memorial Library, the largest collection of psychoactive-drug literature in the world. Ryder worshipped JD Salinger and The Catcher in the Rye growing up, and still does. She felt a fierce connection to the classic of teen angst and alienation. "I think, even, if I ever die, and they stick me in a cemetery, and I have a tombstone and all, it'll say 'Holden Caulfield' on it, and then what year I was born and what year I died, and then right under that it'll say 'Fuck you,'" she once told Vogue.

Throughout her career, Ryder has played meaty, interesting, real women, in a way that made you deeply feel. Kim in Edward Scissorhands, who falls in love with another outsider of a different sort. Abigail Williams in The Crucible, the woman who has an affair with a man and desperately accuses his wife of witchcraft. And beautifully, Susanna Kaysen in Girl, Interrupted, the favorite of every girl or young women who'd had issues with their own mental health.

You could say that Winona Ryder's 2001 "downfall" was near inevitable—she was imperfect in a Hollywood that celebrates and supports Gwyneths, Jennifers, and Sandras. Her anxiety and inability to cope with the oppressive surveillance and commentary on her high-profile relationships garnered little sympathy. She took some designer clothes from Saks Fifth Avenue without paying for them, and was caught in the act. Instead of this inciting a concern for her mental health or well-being, she was vilified. The CCTV footage of her being escorted back in by security guards was shown endlessly on TV and was made a punchline on late-night shows. The angle: Look at these ridiculous celebrities so removed from real life that they decide to steal what they can easily afford.

Male movie stars, of course, can cheat, lie, go on month-long coke binges, crash cars, beat people up, and worse, and still have a career. Other women have managed the transition back to PR-assisted good girl better, but that doesn't fit with the authenticity for which Ryder is loved. For her, this meant a long downturn. She practically disappeared. And now she's back.

Near the end of last year, Vogue declared a "Winonaissance." This is the result of the last few years of 90s nostalgia, sure, but also because we resonate with her again. She spent her 20s coming of age in a similar way to the generation experiencing that right now, in that we can't grow up, and don't know how to. Her struggles with anxiety are familiar to many.

Now she's making up for lost time. She's had a slow but steady flow of minor acting jobs for the last eight years, including a brilliant role as the has-been ballerina in Black Swan , but is back to top billing in the spooky Netflix series Stranger Things. Ryder plays a mother who has to search for her missing child in a small Indiana town in the 80s. Crucially, as critics have pointed out, her casting plays on her enduring appeal, and the nostalgia it evokes. We see her new role, but also feel the presence of all her previous characters. We care about the character, but not as much as we care about Winona Ryder.

So while she'll be Winona Ryder Forever, it seems she's finally escaping the 90s and her—our—extended adolescence.

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