“What makes someone an icon? Is Nelson Mandela an icon? Is Václav Havel an icon? Is the alien from Alien: Resurrection an icon? I don’t know what the requirements are.” Winona Ryder pauses to consider the well-oiled word from the far reaches of the lobby lounge at the Chateau Marmont in West Hollywood. Her cap is pulled down to hide the face of an Edward Gorey beauty rendered in chalk. She sits on her tiny feet as if to keep them warm.
When our waiter arrives with two blistering cups of English breakfast tea, the green-eyed actress wonders if Philip Roth might fit the part of icon. By the time the tea has cooled into twin lakes of still cream three hours later, she has settled on Empty Nest’s Kristy McNichol. “But,” she says, “I would never consider myself anything like that.”
Two decades into her film career, and two years shy of 40, Ryder has developed from a doe-eyed ingénue into a full-grown, albeit delicate, woman. And after a nine-year retreat from the spotlight, the actress who personified the knowing malaise of the late ’80s and early ’90s—as the beautiful freak in Tim Burton’s Beetlejuice, the homicidal girl-next-door in Michael Lehmann’s Heathers and the idealistic videographer in Ben Stiller’s Gen X-defining classic Reality Bites—finally returns with The Private Lives of Pippa Lee, an impeccable arthouse film starring Robin Wright Penn, Blake Lively and Keanu Reeves.
Whereas the younger, more exposed Ryder was the portrait of a tortured thespian on the verge of a breakdown, the grown Ryder seems comfortable in her own skin. And unlike most teen actors who devolve into twisted shells of their former selves, the bookish star has gracefully matured, despite a journey neither straight nor narrow.
Top Image: Shirt by Gucci. Ryder’s own ring.
Stylist’s own T-Shirt and Crown Necklace. Necklace by David Yurman.
Ryder rarely gives interviews, as if rebelling against—or atoning for—her effusive past. “It’s weird,” she says, “the whole concept of an interview. To hold someone accountable for what they’ve said or done when they were younger is bizarre. We evolve, we change—at least I hope we do.” She seldom attends step-and-repeat Hollywood parties. (“I hosted a benefit for this theater company one night with Courtney Love,” she says. “We got photographed on the way in. It was kind of a nightmare.”) She trails off when discussing her private life. “I’ve just been told that news will break next week that I’m pregnant,” she says laughing, “which is impossible.” And just to make sure she has been understood, Ryder adds, “Because, you know, I’m on my… ” Her left hand circles the air just south of her phantom baby bump.
But a strange thing happens when Ryder tries to censor herself. Instead of stifling her words, she continues in a faint whisper, as if simultaneously trying to withhold and share a story. She does this often with trivial anecdotes. She cringes, for example, when recalling her introduction to rapper Dr. Dre: “I was like, Oh, thank god. I just got off a long flight and my ears are still blocked. Can you help?” The same thing happens later, with weightier issues. When discussing the death of her friend, actor Heath Ledger, she wonders, “What happens to you when you die? Does your energy dissipate? Is there something whole about your soul that keeps going?”
When embarrassed, Ryder’s soft-spoken lilt becomes altogether inaudible. “I was once published under a different name for a short story I’d written,” she says, so shy that it becomes difficult to hear her. “I wanted to know what it felt like to have people enjoy something and not know it had anything to do with me.” But wouldn’t the recognition validate the work? “Well, I can’t listen to Wagner because he hated Jews. I can’t read Émile Zola—I mean, I love Émile Zola, but he had some scandals that were kind of scary—and I worship Woody Allen, but he had his thing, too. I struggle with the age-old question of how to separate the art from the artist.”
Biographies have been written about Ryder’s youth, all of them unauthorized. E! broadcast her True Hollywood Story, which, despite the title, she says, “is just wrong—even the flattering stuff! I didn’t watch the whole thing, but my dad was like, ‘Oh my god, they’re making the commune look like Waco.’” She was raised on 380 acres of deadwood in Mendocino, California, by her mother, Cynthia Palmer, a writer, and her father, Michael Horowitz, an author, editor, antiquarian bookseller and, according to Ryder, cultural Zelig. “He was at Altamont [the music festival organized by the Rolling Stones, now infamous for its violence] and he was at the Last Waltz at the Fillmore [the Band’s final concert]. He took me to my first concert, the last Sex Pistols show, when I was 7.” Ryder grew up in the enlightening company of adults like her godfather, the ’60s counterculture guru Timothy Leary, beat poet Allen Ginsberg and musician Tom Waits, for whom she once babysat.
Bodysuit by American Apparel. Sweater by Obesity and Speed. Ryder’s own rings.
Her first big role came in 1986 with the release of the teenage-love tale Lucas, but it was Beetlejuice and her relationship with actor Johnny Depp, which began when she was 17, that shoved her in front of the flashing lights. For four years, she and Depp swooned over one another while Hollywood swooned over them, a frenzy fed by their co-starring roles as suburban star-crossed lovers in Edward Scissorhands. “Things changed for me when I met Johnny,” she says. “This weird thing happens when you’re written about in magazines, where you start to think, This is who I am. This is how I have to be. I felt restricted and pressured into being the way people perceived me. It was hard for me to find my footing. The Johnny thing made me really afraid of the press because, even though it was about him, I was beside him the entire time.”
She and Depp split in 1992. (Depp, for his part, has a tattoo, now edited to read “Wino Forever,” commemorating the relationship.) Not long after, Ryder began dating a dreadlocked Dave Pirner, lead vocalist of alt-rock band Soul Asylum. “I did a few movies and I felt like I had allowed myself to become a more open person,” she says. Comments like these enforce the sense that Ryder’s life has been a steady negotiation between the desire for genuine human contact and a tireless, self-protective whisper in her head that warns against it. “I hate the thought of having to live my life being skeptical of everyone,” she says. “I’ve just always wanted to find someone who understands what I do, who doesn’t think my life is so glamorous and who doesn’t really care. In a way, actors really do fit that category, but I would want to be with one who had been around a while. Newly successful people are just as scary as non-celebrities.”
Ryder, who also dated actor Matt Damon for two years, gets along, for the most part, with all of her celebrity and non-celebrity exes. “Matt couldn’t be a greater, nicer guy. I’m really lucky that I’m on good terms with him,” she says. “With Johnny, it’s like we’re good, but we lead very different lives.” Ryder adds, “I was out at a bar with a friend who said, ‘Do you realize that in America you’re never going to be able to meet a guy who knows nothing about you? Everyone will have preconceived ideas about who you are.’ I got so bummed out. I’d never really thought about it that way.”
Shirt by Alice + Olivia. Jacket by Hanii Y. Ryder’s Own Rings.
Constant media scrutiny—compounded by exhaustion and the normal anxieties of a woman about to turn 20—convinced Ryder to seek psychological treatment in 1990. “I remember waking up one morning,” she says of her breaking point. “I looked in the mirror and thought, Am I going crazy? So I checked myself into a hospital where I stayed for a few days. I was surrounded by people who had been molested and abused. I felt like they hated me, didn’t know what the fuck I was doing there and wanted me to get the hell out because what the fuck did I have to complain about?” A smile builds across her face when she adds, “When it was my turn to talk in group therapy sessions, I was like, I’m just really tired because it’s hard to be famous.”
Out of her experience at the hospital came an appreciation for the marginalized women she met during her stay. And then Ryder cracked the spine of Girl, Interrupted, Susanna Kaysen’s 1993 memoir about life in a psychiatric institution. “What I found so interesting,” says Ryder, “was that if you did something sort of normal-crazy, like taking a bottle of aspirin, you were locked up for years. Now, they won’t hold you if you say you’re schizophrenic and you’re going to kill yourself or someone else. You can thank Reagan for that one.” In 1999, after years spent trying to adapt the book to film, Ryder starred in and produced Girl, Interrupted, for which Angelina Jolie won the Academy Award for best supporting actress.
It was Ryder’s first serious bid for critical acclaim since her Oscar-nominated turn in Nicholas Hytner’s 1996 version of The Crucible. But members of the press were quick to reduce Ryder to a scorned actress overshadowed by a rebellious, brother-kissing man-eater with chaise-lounge lips. “I never had any bad feelings about Angelina,” she says. “And I was hurt that people thought that. Everyone assumed I was really jealous because I thought this would be my vehicle. We said from the very beginning that the actress who played Lisa would probably win an Oscar, because it was the big, great, showy part. But I always related to Susanna.” In a way, Ryder was responsible for jump-starting Jolie’s career. “I fought very hard for her to have that part, and I never really felt like I got the chance to know her.” Did Jolie ever personally thank her? “I feel like it won’t read in print very nicely if I say that wasn’t really her style,” she says. “But she seems to be a completely different person now.”
Sweater by Zadig & Voltaire. Jeans by J Brand. Shoes by Pour La Victoire.
In December of 2001, Ryder was arrested for shoplifting at Saks Fifth Avenue in Beverly Hills. Ryder won’t talk about it. We move on, but before doing so, she touches my arm and, as though forgiving me for asking, says, “I understand. I’m curious about other people, so I have to understand when people are curious about me.”
Despite whispers to the contrary, Ryder insists it was her aversion to shoddy filmmaking that has slowed down her career. “One of the worst things you can be is mediocre,” she says. “I get offered a lot of studio things—you wouldn’t believe some of the stuff I turn down that then gets packaged with two movie stars. I’m getting a lot of horror movie offers, too, but I just don’t like the ones where you have to cut off your own arm to escape the killer. Or,” and here she imitates the nicotine-soaked baritone that plays over trailers for budget slashers, “What if people did horrific things to your daughter and then they were trapped inside your house?”
One of Ryder’s many delightful quirks is her odd out-of-time sensibility. She groans, for example, when discussing “TZM” cameras. She swears she can’t understand the allure of “Facehook.” And while she thinks tweeting sounds funny, she has yet to do so because she doesn’t “have a MySpace account.” Her disdain palpable, Ryder says, “I don’t know what the future holds for the Internet.” Not wholly unaware of how charmingly anachronistic she sounds, Ryder adds, “I don’t know if it’s because of my love of books and the pages and the print—there’s just so much romance in them—but I hate all these doublespeak abbreviations like ‘OMG’ and ‘LOL.’ I still don’t know if that means ‘Laugh Out Loud’ or ‘Lots of Love.’”
This may explain her appreciation for Pippa Lee, a thoughtful, character-driven ensemble drama about women in the lives of successful male publishers—worlds apart from the Saw franchise. “Most actors only agree to work on films for a specific amount of time,” Ryder says. “But I was like, Keep me up there the whole time. Little did I know it would be in Danbury, Connecticut, without a rental car, living off of a highway. I had to rely on Keanu, who had the car he drives in the film, to get me to Starbucks—that’s how low-budget it was.”
Ryder’s part is small but pivotal, and in only a few scenes she dares the camera to pan away from her quirky brand of crazy as Sandra Dulles, an adulterous mess of insecurity and self-interest. “I loved the idea of playing an egomaniac,” she says smiling. “My character doesn’t do anything for anyone but herself. She wants to be amazing and so she latches on to anyone she can.”
Shirt by Marc Jacobs.
Written and directed by Rebecca Miller—wife of Daniel Day-Lewis as well as the daughter of playwright Arthur Miller and photographer Inge Morath—Pippa Lee felt like a homecoming for Ryder. “I’ve known Keanu since I was 16, so he’s sort of like a brother to me. I know Robin from when I used to live in San Francisco. I know and love Rebecca through Daniel [with whom Ryder starred in The Crucible and The Age of Innocence] and Arthur [who wrote The Crucible and its screenplay].”
Sandra might not be richest role of Winona Ryder’s career, nor will it be her crowning achievement. But after all of the good, all of the bad and, yes, a touch of ugly, Ryder has finally gotten to the point in her life where acclaim and validation are no longer necessary. She leans in as if to reveal her greatest secret yet: “I’m the happiest I’ve ever been. I’m not going to turn into Gloria Swanson and sit in my mansion watching my movies, with a crazy cigarette holder,” she says. “But I feel so blessed to have done the things that I’ve done.”
Back when she was still a teenager, her friend Sean Penn wagered $500 that she would tire of acting by her 30th birthday. “But that hasn’t happened yet,” she says as the sun sets on Hollywood. “I still don’t sleep the night before my first day on set. It’s a struggle to make good movies today, and I’ve certainly been in films I’m not thrilled with. I just have to be patient and good in my own life, and know that if I never work again, I still had a great career.”
WINONA’S FAVORITE HOTEL: CHATEAU MARMONT, LOS ANGELES.
[Photography by Andrew MacPherson, Styling by Anda & Masha. Hair by Yiotis Panayiotou @ Celestine. Makeup by Monica Blunder @ The Wall Group. Manicurist: Jenna Hipp @ Celestine. Digital Tech: Nate Caswell @ Industrial Color. Photographer's Assistant: Alex Almeida]