Winona Ryder has this problem, and as problems go it's pretty solidly in the first-world category, she knows, but it's a problem, still: She'll be having a conversation with somebody—an interesting conversation, the kind two regular people have when they discover a mutual admiration for, like, Philip Roth's American Pastoral or something. And then suddenly the person she's having the conversation with will say something to her that reminds her that (a) she is Winona Ryder, the famous actress, and (b) nearly everyone she meets already has "this whole idea" of who she is, already thinks they know everything there is to know about her, more or less. And inevitably when this happens, she starts thinking about what it is people think they know about her, which is never a good idea, and the conversation never really recovers.
And it's interesting that we're talking about this right now, Ryder and I, because for an hour or so we've been sitting in a booth in the ground-floor restaurant of a hotel in Manhattan, one of those almost purgatorially anonymous luxury filing cabinets uptown by the park, and we've been having the Philip Roth conversation, metaphorically speaking. Ryder—tiny, in a newsboy cap and a City Lights Bookstore T-shirt and a tangle of gold necklaces—has been talking about the Saw franchise and Michelle Pfeiffer and Alice Doesn't Live Here Anymore and the reason the chaise longue was invented (corsets, fainting) and melatonin and her crush on the young Anthony Hopkins circa 1977's Audrey Rose. She's told me embarrassing stories about famous people who deserve to have embarrassing stories told about them.
(A Mel Gibson anecdote: "I remember, like, fifteen years ago, I was at one of those big Hollywood parties. And he was really drunk. I was with my friend, who's gay. He made a really horrible gay joke. And somehow it came up that I was Jewish. He said something about 'oven dodgers,' but I didn't get it. I'd never heard that before. It was just this weird, weird moment. I was like, 'He's anti-Semitic and he's homophobic.' No one believed me!")
It's been great, really. But everything I think I know about Winona Ryder, famous actress, is sort of burning a hole in my pocket, and I'm starting to wonder if she's doing this on purpose, trying to blow past that moment where we acknowledge the room's considerable elephant population. When she does allude to the elephants, it's in passing, as if I wouldn't know they're there—she says things like "My first relationship was very public" (you don't say!) and bats a set of eyelashes as dark and lush as marabou dipped in squid ink, then moves on, and if it's a gambit it's working pretty well so far, honestly.
We do get to talk about Darren Aronofsky's movie Black Swan, an arty-pervy head-wrecker that might be Aronofsky's best film, or 2010's, or the most delu-classy exploitation film released by a major studio since Showgirls, or all of the above. It's basically a girl-world version of Aronofsky's The Wrestler—instead of waiting for Randy the Ram's heart to explode, we're waiting for Natalie Portman, as a ballerina driven to the edge by her boundary-defying mom (Barbara Hershey) and a preening evil-Balanchine type (Vincent Cassel), to go crazy or break a leg, and feminine signifiers like lipstick, ribbons, feathers, toe shoes, cake, tulle, blood, and orchids stand in for 'roids and staples, but the awful anticipation is the same. Ryder's in it for maybe ten minutes, and all of them are crazy and important. She's the former ingenue who refuses to go quietly when Cassel pushes her aside in favor of Portman. The character is a raging mascara-smeared wreck who embodies, in a Ghost of Christmas Future kind of way, everything the movie has to say about the terrible toll performance extracts from young women.
It's about ballerinas, but it could just as easily be about actresses. And maybe it is, really. Ryder's 39, a former ingenue herself, and casting her as the cracked-mirror version of Portman, who's ten years younger and an emplar of a breed of actress that essentially didn't exist as a Hollywood commodity pre-Winona, opens up all kinds of meta-resonances. It's the best role Ryder has had in years, but you could imagine some actresses having second thoughts about steering straight into that subtext.
Ryder didn't, though. "I thought it was a cool parallel," she says. "Being replaced by the young thing. I know that definitely happens in Hollywood. It's harder to find good roles, and suddenly there's new girls. I'm at that age I've been warned my whole life about."
Think about J. J. Abrams's Star Trek reboot last year, where Zachary Quinto, just six years younger than Ryder, played Spock, and Ryder, in a weird Grey Gardens head scarf, played his mom, and how weird that was, even in the context of a movie involving time travel. Ryder made her name in a series of coming-of-age, losing-of-virginity kind of roles; she's outgrown that slot without quite growing into another one. To put it in merciless Hollywood-math terms, she's too old to coquette and too young to cougar. That's one reason she's in an odd place at the moment. That's the simple answer. There are other answers, but it'll take us a minute to get there.
She was born in 1971, in a farmhouse somewhere outside Winona, Minnesota, to writer Cynthia Palmer Horowitz and writer/rare-book dealer Michael Horowitz, who tied off her umbilical cord with a sterilized shoelace. She spent a few years of her life on a commune before fifth columning into small-town Petaluma in junior high, grew up with Timothy Leary as her godfather, knew Ginsberg and Ferlinghetti as friends of her parents. Read The Catcher in the Rye and developed a lifelong Salinger obsession. Took acting classes. Got cast in 1986's Lucas, playing a friend of Corey Haim's. ("There was Winona, this little frail bird," the film's director, David Seltzer, told Rolling Stone in 1989, in Ryder's "Hot Actress" cover story. "She had the kind of presence I had never seen—an inner life. Whatever message was being said by her mouth was being contradicted by the eyes.")
Her parents worried. "They'd heard all the Judy Garland stories," she says. She had to beg them to let her do Lucas. One of them always came to the set with her, and to other sets thereafter. It kept her together, or at least together-er, as a lot of her peers, stage-parented less conscientiously, spun off into Judy Garland stories of their own.
Her dream was to become a weird character actress, like Ruth Gordon from Harold and Maude. She was drawn to roles that get introduced in screenplays as follows:
That's from the screenplay for 1988's Beetlejuice, by Michael McDowell and Warren Skaaren; she got that part, despite mistaking Tim Burton for a prop guy at her audition. So began a streak where—even though she never became a huge box-office draw—every project she touched had a pop life. Or maybe she brought the pop life with her wherever she went. Lydia Deetz basically pioneered the whole sullen-goth-chick thing in mainstream culture. (The first Hot Topic store opened the following year, in a mall just off the 405 freeway.) Heathers flopped but invented a genre—you don't get Buffy, Mean Girls, or Blair Waldorf without Ryder's teen-angst body count.
She was working too hard. She had to drop out of The Godfather Part III at the last minute; Sofia Coppola stepped in. But by then it was the turn of the '90s, Nirvana was tuning up somewhere out in Washington, and quirkyindiewhateverism was about to have a moment in the spotlight, a moment for which Winona—luminous and vulnerable and well-read and skeptical in fundamental ways about all this attention—is sort of the perfect movie star. Hip musicians named songs after her—countrified sad-boy ballads, sarcastic feedback mash notes. Later on, she returned the favor by dating a bunch of hip musicians. Not as many, she says, as everybody thinks. But after she went out with Dave Pirner from Soul Asylum, she was linked to a vanload of indie frontdudes; a Winona rumor regarding the lead singer became one of the ways we knew a band had both arrived and sold out. Hence the quote, commonly attributed to Courtney Love: "You're no one in the rock industry unless you've feuded with me or slept with Winona Ryder."
She met Johnny Depp at a premiere; they experienced what, in retrospect, seems like a gentler, bygone-age version of hyper-public tabloid-hounded courtship; they got engaged; he got a new tattoo.
For an actress so indelibly associated with Generation X, Ryder's '90s filmography was heavier on corset-and-fainting-couch stuff than you remember. Still—she owned the decade, Zeitgeist-wise.
Three Winona Ryder movies from the '90s, in which the essence of Winona Ryder and/or the dominant sensibility of the '90s is encapsulated:
Night on Earth, directed by Jim Jarmusch, 1991. Ryder as a scrappy L.A. cabdriver who picks up a casting agent (Gena Rowlands) at the airport. Her tough-cookie line readings don't really play; Ryder the actress is too visibly gaga for Rowlands. They talk past each other, like people do in Jim Jarmusch movies, and then Rowlands offers Ryder a part in a movie. She declines; her goal is to become a mechanic. "Are you saying you just wouldn't be interested in being a movie star?" Rowlands asks. "Nah," Ryder says. "Look, lady, I like the movies and all... but that's not a real life for me, y'know? I'm sure there's tons of girls who want to be in movies... " She stops, frustrated—it's not coming out right. "I have everything planned out. Everything's going just right for me now.... But, y'know, I mean, I appreciate it." This is the key to the whole thing—like all the great rock stars of her era, Winona made you think she could take or leave it, that she'd be just as happy going off somewhere and rereading Raise High the Roof Beam, Carpenters for the thirty-seventh time, whether or not this was an illusion.
Reality Bites, directed by Ben Stiller, 1994. The movie is Gen X halfheartedly pleading its case to history; the only jokes that really land are the ones Stiller aims at MTV-sanctioned faux-alternative culture, because as the former star and co-creator of MTV's Ben Stiller Show he's biting a hand that's fed him. But there's one scene in which Ethan Hawke, as Ryder's asshole-sage roommate–love interest, puts down the Pringles and his copy of Being and Time long enough to tell her, "All you have to be by the age of 23 is yourself." Ryder was about that age here, and had already checked herself into a psychiatric clinic, for anxiety and depression. ("I got really wiped out, and I had a semi-breakdown. I wasn't sleeping, I didn't know who I was because of different roles," she says.) She whispers back, "I don't know who that is anymore," and for a minute it's not the character talking, it's Ryder, and a gulf opens up in the story and threatens to swallow her. Bonus: Around the fifty-nine-minute mark, in the diner scene, Winona totally invents that face Kristen Stewart makes at every awards show.
Girl, Interrupted, directed by James Mangold, 1999. It took Ryder six years to get this adaptation of Susanna Kaysen's mental-hospital memoir made; it took Angelina Jolie less than two minutes to walk off with it, with a fearless, braless, carnivorous performance that got her an Oscar/created a monster. But as Kaysen, in a role that requires a lot of observing and smoking and furious journaling and offers fewer opportunities to go all Randle McMurphy than Jolie's does, Ryder does deeper, trickier work. She's incredibly cool in this movie, the female neurotic as James Dean rebel, wearing her false bravado like a sidearm. Watch the flashback: Winona, with a cigarette and a leather jacket, dancing to the Chambers Brothers at a frat party, too cool to be there but there nonetheless. Some dork asks her what she's going to do after graduation. "I'm going to join the Krishnas," she says, and rolls her eyes. That frail bird from Lucas has left the building.
She'd mastered something, in that last one, but nobody really noticed. After that there was Autumn in New York, where she dated Richard Gere's old ass, and then her arrest, in December 2001, for shoplifting about $6,000 worth of Gucci and Marc Jacobs merchandise from Saks Fifth Avenue in Beverly Hills. (Historians will remember it as the first major celebrity-bad-behavior story of the post-9/11 era, a sign that it was okay for us, as a society, to be preoccupied with stupid bullshit again—and, as a bonus, since it was a story about a famous actress getting popped for stealing clothes she could probably have gotten for free just by making a phone call, a rebuke to that whole death-of-irony thing.)
This is where our conversation sort of gets weird. Ryder has been talking about certain aspects of contemporary culture that confuse her, as if she's a time traveler—which she kind of is! From the last century! She's still figuring out how to work her iPhone. She talks about TMZ but calls it TZM. She doesn't know who Justin Bieber is. She says she's never seen a reality-TV show, and she seems genuinely puzzled and horrified by the existence of Celebrity Rehab.
"I mean, who would want to go through that, on TV?" she says.
We spend a few surreal minutes explaining Celebrity Rehab to Winona; the paradoxical way Dr. Drew helps patients mind-warped by fame with everything that's wrong with them except their desire to be famous; the ongoing struggles of Jeff Conaway, who played Kenickie in Grease, then resurfaced in Dr. Drew's clinic, undergoing chew-your-arm-off withdrawal from painkillers in front of VH1's cameras.
"Yeah," Winona says, "those things. I think they're more powerful than people think. People think, 'Oh, heroin's the hardest,' but pills can be..."
Didn't you have sort of a moment with those?
"I did," she says, "but it was—I broke my arm in two places." (This was in 2001, on the set of the Adam Sandler movie Mr. Deeds.) "For about a month, I had to take it. But then I just kept taking it for, like... maybe three more weeks. But the thing I do remember is that once my arm was okay and they were still there, you kind of like... "
What I want to say is, Wait a minute. According to a probation report archived at the Smoking Gun's Web site, when Ryder was arrested, police found a syringe, bottles of Demerol and diazepam, six Valiums, forty Vicoprofens, two Vicodins, two Percocets, a Percodan, and a morphine-sulfate capsule in her purse. In 2002, a Dr. Feelgood type named Jules Lusman had his license pulled by the Medical Board of California after an investigation determined that he'd "prescribed or administered controlled substances without good faith exams" to clients like Courtney Love and "E. T.," which was short for "Emily Thompson," Ryder's prescription-pad alias. In an August 2007 Vogue cover story, Ryder actually blamed the whole shoplifting situation on pill-related "confusion."
I'm sort of staggered by the way she blows by the shoplifting thing without talking about it, and before I recover she's off in another direction, talking about her parents again, how they always told her to come to them if she was thinking about experimenting with drugs, how they talked to her about the importance of set and setting, a phrase coined by Leary, who used to take her to baseball games and help her with her homework. She was telling us about how it's hard to rebel when you grow up in a world like that.
"I went through this stage where I was really square," she says. "We lived on this commune, and there was this beautiful waterfall. And there'd be a lot of kids that were naked. But I was in a bathing suit."
Honestly, there's something cool about her unwillingness to serve up the shoplifting story as a celebrity-profile data point; it indicates that she's still embarrassed by what happened, like any normal human would be. A few weeks later, when we ask her about the incident directly in a follow-up phone call, she says she tries not to talk about it when she does things like this, that she's been told that if she talks about it once she'll have to talk about it again and again, with everybody, and it's clear from the way her sentences start trailing off into false starts that she doesn't like revisiting it herself: "It's just like, nothing... I don't, like, even... I mean, I know people still... I apologize, 'cause I understand the curiosity. I just don't really want to go there." She then apologizes, which makes me feel like a creep for asking.
Still, the pill thing matters, because she basically dropped out of sight for four years after it happened, effectively putting an end to the Winona Era. Fun movie-dork party game: Imagine a parallel universe where there is not this Winona-shaped hole in recent cool-movie history. She'd have been one of the Dylans in Todd Haynes's I'm Not There, for sure. Maybe the object of Jim Carrey's amnesia in Eternal Sunshine of the Spotless Mind. She could have been a Tenenbaum.* Maybe even a Cullen.
* Yes, Wes Anderson shot The Royal Tenenbaums before her arrest. But let's say, in this parallel universe, Winona doesn't drop out of Godfather III, which creates a butterfly-effect ripple across the space-time continuum: Sofia Coppola doesn't replace her, which means Sofia Coppola's performance isn't eviscerated by the press, which means she continues to act instead of pursuing a career behind the camera, and the adaptation of Jeffrey Eugenides's novel The Virgin Suicides falls to a fresh-off-Rushmore Wes Anderson, delaying Tenenbaums by two years. Winona plays Margot, obviously. During the film's opening weekend, syndicated radio personality Glenn Beck is mauled by a tiger.
Instead she resurfaced in 2006 as an occasionally topless rotoscoped cartoon in Richard Linklater's A Scanner Darkly. Aside from that movie and Star Trek, she's been in limbo. It's hard not to look at her arc and the arc of somebody like Robert Downey Jr., who starred with Ryder in 1988's 1969 and then again in Scanner, and was a far bigger mess than Ryder before he became a superhero, and wonder if Hollywood and/or the American viewing public has different rules for fallen women and fallen men. But maybe she would have wound up here anyway.
"It's hard to imagine a time where Meryl Streep wasn't the first choice for everything," Ryder says, "but I was reading some article, and she said something like, 'Yeah, when I was around 38, 39, I turned to my husband and said, "Should we just call it a day, or should we try to kick the can down the road?" ' It was so weird to me to think about movies without her in them. But a lot of great actresses have chosen that."
She's thought about it. She wants to have kids. It's the only thing that scares her about getting older, the thought of missing that window, and the other side of it: "If I wanted to have a family now, would I be able to come back to work in a couple of years?"
Circling back around to Black Swan, I ask her if, beyond the obvious ingenue-succession angle, she saw anything of herself in Portman's character, who is young, and who is forced, via this weird predatory-mentor thing she has with Cassel, to dig into her dark side. Ryder once said that a big part of her early-twenties breakdown had to do with the stress of acting itself, how the reach for emotional truth often involves dredging up stuff you shouldn't be made to dredge up without the guidance of a licensed therapist.
"I did, definitely, but I also loved it.
"I think, yeah, there's a lot of danger in that," she says. "And I think that made me freak out a little bit. I think I was playing with fire there, for a while."
Alex Pappademas is GQ’s staff writer.
A version of this story originally appeared in the January 2011 issue with the title "Winona Forever."
