Winona Ryder Forever: How the Gen-X Icon Kept Her Cool


“I’m so sick of people shaming women for being sensitive or vulnerable. It’s so bizarre to me.” Winona Ryder is talking about the press and its tendency to pathologize female emotions, but she could also be talking about her lead role in Netflix’s Stranger Things playing a frantic mother whose child has mysteriously disappeared. The supernatural, Spielbergian ’80s-era drama, created by newcomers Matt and Ross Duffer, has attracted an enthusiastic and vocal viewership, but Ryder seems almost confused by some of the questions she’s been asked while promoting the show. “They use the word passion. ‘Did you feel passionate about it? Is it a passion project?’ ”

This isn’t the only time I’ll be treated to her strangely charming “I just got here from another planet” tone. Ryder seems more comfortable with discussions that exist one meta-level up, analyzing the perplexing ways of the press — even as we sit for two hours talking at the white-hot center of celebrity-interview clichés, the lounge of the Chateau Marmont, where several different waiters hover over our table, more attentive and slow to exit than nurses in a nicu ward.

“I’m getting asked a lot, ‘You don’t have kids, so how do you know how to act like a mother?’ I know nothing could compare, and I haven’t had that experience, but when my niece was born, I felt like I would jump in front of a car and die for this little person I didn’t even know yet.” Ryder pauses, then returns to talking about her character, Joyce Byers, a store clerk with a deadbeat ex who’s unraveling from frustration and grief. “I actually felt tremendous compassion for her. I feel like she was one of these people that had dreams [for her life]. But she had kids. And it made me think of all the women that I know who have kids, who when they talk about [anything negative about their lives as mothers], they always say, ‘But I love my kids, I wouldn’t trade them for the world.’ Like they feel guilty for even hinting that they’d want something outside of kids! It’s a weird thing.”

Ryder is dressed exactly the way I remember lots of brainy-but-cool girls dressing in the late ’80s (possibly in an effort to look just like Winona Ryder): white T-shirt with an abstract design on it, red cardigan, tangled jeweled necklaces, old jeans, maroon men’s shoes. This is the Gen-X-star-who-hangs-with-indie-film-and-rock-gods uniform, but somehow, on Ryder, it doesn’t look dated. At 44, she can say “weird” and “like” and stare into the middle distance with those big brown eyes straight out of a Keane painting and sound just like an appealing hybrid of enthusiastic teenager and world-weary adult.

But then Ryder’s odd blend of innocence and sarcasm has always been central to her appeal among Gen-Xers. She was America’s original Manic Pixie Dream Girl, one far more brooding than the smoother, more cheerful Natalie Portman version of Zach Braff’s fever dreams. From her first appearance at age 14 as a tomboy in the film Lucas to her unforgettable eye roll in Heathers, Ryder seemed to give shape to all the strengths and flaws of an entire generation. She was hip and alternative well before those words became just another way to sell cola and all-wheel-drive hatchbacks, which was also well before most high-school kids understood that they had fashion choices beyond bright-colored clothing and hair permed to look like Jennifer Grey’s in Dirty Dancing. While most of our so-called style icons were parading around in sequined blouses and tying scrunchies into their Sun-In-ravaged hair, Ryder dyed her hair dark brown and wore red lipstick and men’s suit jackets. She name-dropped authors and favored vintage gowns and dated Johnny Depp, for Chrissake, who’d just been crowned the boy king of the realm. But she also had a self-conscious, almost apologetic way of holding herself, like she wasn’t entirely comfortable in her own skin.

In rewatching Ryder’s most notable films from the late ’80s and early ’90s, her self-aware, jittery demeanor reveals itself as a big part of what made her so transfixing. Young Gen-Xers were nothing if not overly self-conscious and awkward, and Ryder personified that romantic unease. In her most memorable roles — in Beetlejuice, Heathers, Edward Scissorhands, Reality Bites — her characters are contradictions, open but self-protective, emotional but cynical, naïve but edging toward ennui. In Reality Bites in particular, a film awash in Gen-X clichés (some accurate, some cartoonish), Ryder toggles between knowing sophistication and childlike goofiness. One minute she’s rolling her eyes, the next she’s aw-shucks-ing along to Ethan Hawke’s scatted monologues about the virtues of slacker idealism.

In one memorable scene, Ryder’s character asks Hawke’s for a definition of irony, and he replies, “It’s when the actual meaning is the complete opposite from the literal meaning.” It makes perfect sense that irony would be the reigning principle of Ryder’s rise to fame. Born in Minnesota and raised in part on a commune in California, she developed an interest in acting after watching old films her mother would play in the family’s barn, a quirky pursuit that landed her at the center of the most scrutinized, unique-snowflake-melting industry on the planet. Her parents moved to Petaluma, California, when she was 11, and even while they supported her desire to become an actress, they did their best to shield her from Hollywood’s influence (“They had the whole Judy Garland thing stuck in their minds,” she says). But she still had to contend with what she calls Petaluma’s “hicks who were also stoners,” who didn’t think she was all that. “I did Beetlejuice, and it was a big movie, but it didn’t help my high-school experience. In fact it made it worse. I was a freak and a witch.”

But what about Heathers? Ryder was 17 when that movie came out. “Even Heathers, which was, like, not a hit at all — I mean over the years it became one, but no. That was the first time I was even described in the script as attractive in any way — ”

“You are very attractive,” our waiter interrupts. (Side note: How do you get a job at the Chateau Marmont if you’re this guy?) Ryder quickly blurts out a surprised “Thank you!” and keeps talking.

The most obvious way that a lifetime of scrutiny reveals itself in Ryder: She doesn’t finish many of her sentences. This trait has been cast as “spacey,” but it appears to me that Ryder has a very expansive way of thinking where several paths open up at once and she can’t decide which one to take. She learned long ago that there were a million things she shouldn’t say — and relearned this more recently when she was promoting the indie film Experimenter last year: “I talked about all this stuff, Stanley Milgram and ‘the banality of evil,’ and they didn’t print a word of it. It was all just ‘Rise to fame! Fall! Scandal! Johnny Depp!’ ” It’s not surprising, then, that Ryder might decide against saying most of the things she thinks to say. But as a result, talking to her can feel like watching someone try to drive when every single road has been closed. What’s fascinating is not that she stops in the middle of the road but that she keeps trying to get somewhere at all. Somehow she never comes across as closed or unfriendly or robotic in the slightest.

“I wish I could unknow this, but there is a perception of me that I’m supersensitive and fragile. And I am supersensitive, and I don’t think that that’s a bad thing. To do what I do, I have to remain open.” She says that sensitive is so often used as a bad word — a euphemism for weak or crazy. “There’s a line in the show where someone says [of her Stranger Things character], ‘She’s had anxiety problems in the past.’ A lot of people have picked up on that, like, ‘Oh, you know, she’s crazy.’ And I’m like, ‘Okay, wait a second, she’s struggling.’ Two kids, deadbeat dad, working her ass off. Who wouldn’t be anxious?

“Even that word, anxious. It’s a bad word. And so like all of these words — it’s kind of what I tried to do with Girl, Interrupted, and why I was so invested in that book and trying to get it made [as a movie]. My whole point was, this happens to every girl, almost.” Yet in trying to remove the stigma our culture places on common emotional challenges by talking about them, Ryder only stigmatized herself more. “I remember I did Diane Sawyer, and I talked about my experiences with anxiety and depression when I was that age. And I think by doing that, maybe coupled with my physical size, there’s this ‘crazy’ thing. And I’ve realized recently it’s literally impossible to try to change that story.”

What’s remarkable about that Diane Sawyer interview, which took place in 1999, is how completely ordinary the feelings of depression and loneliness Ryder describes are. It’s a sign of how dramatically our cultural discussion about emotional experiences has shifted that such mundane revelations could ever be treated as shocking. Toward the end of the interview, Ryder tells Sawyer she feels ashamed that she could’ve ever felt depressed, given all of her advantages. “One of my worst fears is being a self-indulgent person,” she explains, addressing the widely held misconception that somehow money and fame equal happiness. But even these days, when women who talk openly about their struggles still work very hard to project that flavor of sunny, upbeat optimism our culture prefers, Ryder offers us a helpful reminder that feeling conflicted, confused, or just ambivalent is a feature of being alive and not a bug. Emotional intensity, contradiction — these aren’t signs of instability or immaturity; they’re the sophisticated processing of an intelligent, mature adult. In this way, Ryder may just present a powerful talisman of complexity to a culture that embraces knee-jerk optimism, an inadequate guard against darkness or self-doubt.

“I’ve always been super-private and protective of certain experiences and certain friends,” she says. “I don’t regret opening up about what I went through [with depression], because, it sounds really cliché, but I have had women come up to me and say, ‘It meant so much to me.’ It means so much when you realize that someone was having a really hard time and feeling shame and was trying to hide this whole thing … And even the whole, like, sensitive, fragile thing. I do have those qualities, and I just don’t think there’s anything wrong with them. There were times when I let it feel too overwhelming and almost, like, shamed, but I had to just get over that.”

She says that taking a break from Hollywood helped. “I did get a chance to explore during my ‘hiatus.’ I was really lucky, because when all you’ve done is this one thing, you become sort of insecure because this town can be isolating and you don’t feel like you’re capable of doing other things.” She says she got “really into constitutional law for a while and really into linguistics and etymology for a while.” Even when she wasn’t on the public’s radar, anonymity was never easy. In the old days, she says, you could ride the subway and maybe occasionally someone happened to have a camera with them. These days, people are shooting footage of you everywhere you go, and if they ask and you say no … “I’ve been called a cunt to my face by someone who was just saying they were a fan. I was with my parents having dinner. It was actually kind of upsetting, because it upset my parents, and then I got upset. You know that scene in The King of Comedy where Jerry Lewis is at a pay phone? ‘Will you sign the thing, will you sign the thing?’ ‘I hope you get cancer!’ 

“I’m not on social media. I don’t actually know how to use it. And I hear that awful people could then — I say that, and it makes me sound too sensitive.” That’s when I remember that Ryder hit her peak of popularity at a time when people couldn’t come at you on the internet. “I guess you wouldn’t even know how it feels to confront a whole mob of haters,” I told her. “I mean, unless you had a stalker.” Now I’m the one trailing off. Of course Winona Ryder, of all people, had more than one stalker. But she takes it in stride. “Yeah. I did. I had a few. One was really nice. He kept showing up as an extra on movies, and you don’t know. You have to be careful. So I told the director, because he was kinda creepy. And I got this letter in my trailer the next day that was like, ‘I was just trying to get work as an extra! Just so you know, I’m not even obsessed with you anymore, I’m obsessed with Alyssa Milano now!’ So he kind of left me for Alyssa Milano.”

Somehow Ryder has maintained a sense of humor about herself. But between the steady flow of references (Philip Roth, Veep, Marsha Mason movies, Bastard Out of Carolina, Oliver Wendell Holmes) and the wide-eyed mannerisms, she seems like someone who spends a lot of time in her own head. “I have that weird archivist gene–slash–hoarder gene where I keep everything, like every journal. And I think, Do I even want this to exist? But it is sort of interesting to go back and read them. And then all my books …” That sounds a little solitary, I tell her. “Yeah. It’s a struggle because it can get — I can overdo it. Between books and then great shows and nowadays you can watch films instantly — I just discovered that same-day-release thing. But I’ve always been that way. Both of my parents are kind of like that, I don’t know. I’ve always been very nocturnal.”

So this is how we might picture Winona Ryder, after all these years: the former cool girl in repose, grown into a comfortably complicated adult, not in search of a comeback so much as another great book to read. That doesn’t mean her life is simple or easy, of course. “It’s almost like that Twilight Zone episode where that guy says, ‘I just want to be left alone so I can read my books,’ ” she says with a smile. “And then he ends up being sent to a planet where it’s just him and his books, and he’s so happy, and then his glasses fall off and they break.”

Styling By Victoria Bartlett at Management Artists Organization; Makeup by Gianpaolo Ceciliato for Marc Jacobs Beauty at Bergdorf Goodman; Hair by Holly Mills for Tim Howard Management; nails by Casey Herman for Dior Vernis at The Wall Group.

*This article appears in the August 8, 2016 issue of New York Magazine.