The daughter of hippie writers Cynthia Palmer and Michael Horowitz, Ryder was named after a little town near her family’s Minnesota farmhouse, where they lived before moving to a Northern California commune. It was a time when parents of a gifted child still viewed Hollywood as a ravenous wolf from which to protect their daughter, not an opportunity for a future family reality show. Actors didn’t worry about their platforms, but they still risked burnout or worse from drugs and anxiety—all of which Ryder’s battled, sometimes in painfully public ways. Throughout it all, though, she’s been game to poke fun at herself. Exhibit A: the 2002 W cover on which she wears a “Free Winona” tee. Last year, model Sarah Snyder echoed that cheekiness when she wore a T-shirt featuring her own mug shot to her shoplifting trial. Recalling the media frenzy that surrounded Ryder’s own run-in with the law, it’s not surprising that she’s not interested in returning to that time, or even just before, no matter how much we all might miss the golden era when alternative was queen, quick to serve some jovial side-eye to the Spice Girls, MTV’s Spring Break, and the like. How did she get through it? “You just do,” she says. “In the scheme of things, there are much bigger problems to worry about.”
When asked whether she’s aware that she’s a goth icon, Ryder pauses, momentarily speechless. “I feel kind of proud, I guess, but I can’t take full credit,” she says. She cites The Cure’s Robert Smith, but that’s music; she was the queen purveyor of ’90s goth vibes in film (second place: Christina Ricci, who coincidentally starred with Ryder and Cher in Mermaids, a solid contender for a Heathers: The Musical- or Beetlejuice 2-style treatment). “It’s flattering to me. It was a long time ago, but I’ve always felt sort of attached to that time,” Ryder says. “I was just listening to [The Cure’s] ‘Pictures of You’ because I have these old mixtapes that I don’t know what to do with—I’m like, ‘How do I transfer them?’ I still have a tape deck.”
Countless young actresses working today are indebted to the groundwork Ryder has laid, but one of her most vocal fans, Emma Roberts, brings a similar America’s sweetheart-meets-witchy energy to her roles in Scream Queens and American Horror Story. “She made being strange both beautiful and cool,” says Roberts, who watched the savagely satirical Heathers in preparation for Scream Queens, and claims to have all of Ryder’s lines from Girl, Interrupted memorized. “She’s forever a trendsetter without even trying.”
Dress by Giamba, cuff by Erickson Beamon, Ryder’s own T-shirt.