“It’s just kind of epic how wild her mind is and how it goes to all these different corners,” marvels David Harbour, who plays former police chief Jim Hopper, Ryder’s would-be love interest on Stranger Things, the nostalgic sci-fi series set in the ’80s that returned to Netflix for its fourth season on May 27. Harbour says that Ryder sometimes points out minor historical mistakes that series creators Matt and Ross Duffer and the writers have made while they’re shooting. “She’d tell them, ‘This song actually came out in ’85, and you have it in ’83.’ She knew all of these minute, tiny details they didn’t even know, and they had to change things in the script based on that.”
MY OWN ENCOUNTER with Ryder’s wild and curious mind begins when she emerges from a car driven by her boyfriend of over a decade, the fashion designer Scott Mackinlay Hahn, 51.Dressed in a low-key white T-shirt and black overalls, Ryder, who turned 50 last October, looks innocent and nervous, like a kid being dropped off for her first day of school. After locating a relatively private table on the patio at the Four Seasons in Beverly Hills, we settle into a conversation that lasts four hours and covers everything from The Americans (“I still haven’t finished the last season because I don’t want it to end. So I’ve saved it.”) to the paintings of a South Carolina artist named Ment Nelson (“He paints with rainwater. He’s so talented!”) to Laura Dern (“She’s so grounded and smart”) to Australian filmmaker Jennifer Kent (“I really want to work with her”).
The one subject Winona Ryder doesn’t want to talk about is Winona Ryder. Every time I bring up some aspect of her career, she says a few words and then diverts to some other artist or actor or writer she loves. This seems less like a self-protective defense than a genuine interest in a wide range of people and things.
When we finally land on the high-pressure zones of her career, Ryder becomes quieter. “Being talked about, being reviewed … realizing that someone could pause you, could rewind you? It was so overwhelming,” she says.
Ryder landed her first movie role, in the 1986 adolescent rom-com Lucas, at age 13. By the time she was 18, she was a household name. An intensely scrutinizing, particularly nasty brand of tabloid culture sprang up in the early ’90s. The prevailing notion then was that fame and money insulated one from emotional hardship.“I know it’s kind of like ‘Oh, poor Winona,’ ” she says. “But when you’re in pain, pain is pain. But that [realization] took me a while.”
The pressure on young movie stars—and young women in particular—to cement their place in the firmament, against the backdrop of an era when leading men were routinely cast with love interests two decades younger, had to have been crushing. “This business is brutal,” Ryder says. “You’re working constantly, but if you want to take a break, they tell you, ‘If you slow down, it’s going to stop.’ ”
She pauses. “And then it did slow down. So then you’re hearing,‘It’s going to be impossible to come back.’ And then that changes to ‘You’re not even part of the conversation.’ Like, it was brutal.”
Nevertheless, many of us haven’t forgotten that in the late ’80s and early ’90s, Winona Ryder was the conversation. Her porcelain-doll features and half-innocent, half-disenchanted demeanor seemed to embody the essential spirit of Generation X, an unruly mob of idealistic slackers and secretly starry-eyed cynics. No one captured the troubled-but-hopeful vibe of the child of the ’70s like Ryder. Her most memorable roles back then—in Beetlejuice, Heathers, Edward Scissorhands, Reality Bites—share the same tensions between disillusionment and exuberance, eye-rolling and open longing, fierce independence and raw emotional need. Ryder’s extra-large eyes and expressive, silent-film-star face telegraphed one part lost girl, two parts blasé teenager. She managed to appear at once vulnerable and completely over it.
And when Ryder fell in love with Johnny Depp in 1989, they were like a dark fairy tale come to life: two moody, exquisitely beautiful young people haunting the red carpet with the graceful nonchalance of Old Hollywood movie stars. The pair got engaged after just five months and broke up after four years. Depp’s “Winona forever” tattoo eventually crumpled into the far less romantic “Wino forever,” echoing the dissolution of an entire generation’s swagger.
Ryder has kept her own personal life mostly out of view. But she does hint that her breakup with Depp in the early ’90s and the ferociousness of Hollywood culture at the time made life far darker for her than anyone knew. “That was my Girl, Interrupted real life,” Ryder says, referring to the 1999 film she executive produced and starred in about a young woman in a psychiatric hospital, for which Angelina Jolie won the Best Supporting Actress Oscar. “I remember, I was playing this character who ends up getting tortured in a Chilean prison [in the 1994 drama The House of the Spirits],” says Ryder, who credits “an incredible therapist” for encouraging her to imagine being gentle to a younger version of herself. “I would look at these fake bruises and cuts on my face [from the shoot], and I would struggle to see myself as this little girl. ‘Would you be treating this girl like you’re treating yourself?’ I remember looking at myself and saying, ‘This is what I’m doing to myself inside.’ Because I just wasn’t taking care of myself.”
Ryder says that one of her costars in 1993’s The Age of Innocence, Michelle Pfeiffer, supported her when she was struggling, reminding her that everything confusing and unhinged about her reality would fade away and life would eventually feel normal again. “I remember Michelle being like, ‘This is going to pass.’ But I couldn’t hear it.”
“I’ve never talked about it,” Ryder says. “There’s this part of me that’s very private. I have such, like, a place in my heart for those days. But for someone younger who grew up with social media, it’s hard to describe.”
But the cruelest tabloid circus descended in 2001, after Ryder was arrested for shoplifting at Saks Fifth Avenue in Beverly Hills.(She has since explained that after breaking her arm, she was overprescribed painkillers, which rendered her disoriented. That doctor’s medical license was subsequently revoked.)
And then she disappeared. “I definitely retreated,” Ryder explains. “I was in San Francisco. But I also wasn’t getting offers. I think it was a very mutual break.”
“It’s so interesting when you look at the early aughts,” she says. “It was a kind of cruel time. There was a lot of meanness out there…. And then I remember coming back to L.A. and—it was a rough time. And I didn’t know if that part of my life was over.”
Because of these experiences, Ryder has been mindful of how her younger costars on Stranger Things are coping with the attention the show has brought them and how they’ll adjust once it wraps. (The show will end after a fifth season, set to air in the next year or so.) “I want the kids to understand, this does not happen,” she says of being on a show so zeitgeisty that people are clamoring for your attention. “This is really unusual. And I’m always telling them, ‘The work is the reward!’ Because when I was that age, it was so hard to enjoy the fruits of my labor.”
The Duffer brothers think Ryder’s guidance has been incredibly useful to her younger costars. “She’s talked to the kids about what celebrity is like and how the press can be and the anxiety and confusion that comes along with celebrity,” says Ross Duffer.“I think she’s really helped them. I know she’s specifically helpedMillie [Bobby Brown, who plays Eleven on the show] a lot to work through that. And that’s something that no one else can help with, really, because so few people have experienced it. It’s not something I understand. It’s not something that, you know, even a parent would understand.”
THE SENSITIVITY THAT MADE Ryder’s Hollywood trajectory so painful also seems to be her superpower as an actor. Harbour recalls that while they were filming a scene in season three of Stranger Things where Hopper is shooting at Soviet guards, Ryder “started talking about what these normal Russians would enjoy, saying that these people aren’t in control of their lives. And I was like, they’re just the bad guys.”
“She is just nothing but empathy,” Harbour adds. “I think her vulnerability and her big heart is really an anomaly in this business. We all as artists have a certain sensitivity. But to rise in the ranks of the film industry? She just doesn’t have any of those shells.”
“She’ll connect with anyone on set,” offers Ross Duffer. “She loves just getting to know people and talking to them. So it doesn’t matter whether it’s another actor who’s number two on the call sheet or it’s a PA who happens to be handing her water.”
The Duffers say Ryder’s input indelibly shaped the role of Joyce Byers. “We originally just thought of Joyce as this strong, devoted, worried mother,” Ross Duffer explains. “But then suddenly Winona brings an entirely new flavor to it, and we just thought about how much fun we could have with her, getting involved in the supernatural.” Ryder and the Duffers talked about their favorite childhood movies, he continues, including Close Encounters of the Third Kind, “when Richard Dreyfuss’s character gets obsessed and makes a mound out of his mashed potatoes.” Soon Joyce became a multidimensional character, not just pivotal to the central plot but also helpful in drawing great performances out of the younger actors. “Winona brings it 100 percent every time,” says Matt Duffer.“I think that makes a big difference to the other actors, especially when she’s working with the kids.”
“It’s always been about the craft with Winona,” says longtime friend Keanu Reeves, who met Ryder in L.A. in the late ’80s and worked with her several times, including on Bram Stoker’s Dracula and A Scanner Darkly. Reeves was struck by Ryder’s intelligence and her sense of humor, but he says what sets her apart is that she “embodies a kind of vulnerability and a backbone at the same time. You believe her. She’s grounded. You feel the wholeness of her characters.”
In Stranger Things, Ryder adds a new layer to her usual authenticity and emotional presence: great comedic timing. “The more we’ve worked with her, we’ve discovered how funny she can be,”says Ross Duffer. “I mean, she’s really, really funny.”
It’s almost as if Gen X’s favorite gloomy teen has grown into a secure adult, finally comfortable enough in her own skin to share her wisdom and sense of humor with the world. When Ryder’s boyfriend, Hahn, shows up to drive her home, we all end up chatting amiably for almost another hour. It’s easy to imagine that he’s partly responsible for her newfound ease and confidence.
“I was just telling her about that interview we saw with Harvey Fierstein…” Ryder says to Hahn, then she turns to me. “He grew up on Fire Island.”
“Yeah, I grew up in Harvey’s prime, when those guys were truly trying to have a normalized voice and piece of the world. And they had to hide everything,” says Hahn.
Having mentioned that she cried at the end of Fierstein’s interview, Ryder says to Hahn, “You were emotional too!”
Witnessing Gen X’s moody, daydreaming heroine wind up with another empathic, romantic soul feels like a kind of closure, the inverse of the gloomy generational vertigo incited by the way things have gone for so many of Ryder’s contemporaries. “We have so much in common,” Ryder says of Hahn. “We connected on so many levels. But it was amazing that he’s not in this business…. I really did try to keep it quiet.” (Hahn is so far removed from showbiz that when he first met Ryder, he didn’t even recognize her. “He thought I was Milla Jovovich,” Ryder says, laughing. “He told me I was great in The Fifth Element.”)
The quiet life is, after all, Ryder’s version of a best life. That’s where the fierce independence and raw emotional need of youth tend to balance themselves out in maturity: far from the spotlight, among old movies, old books, and old friends—the emotional equivalent of an old theater with just a bed, a bathtub, and a bike in it.
Hair: Edward Lampley for Oribe; Makeup: Maki Ryoke for Chanel Beauty; Manicure: Olivia de Montagnac; Production: Nicole Tondre at Hen’s tooth Productions; Set Design: Heath Mattiolo. See The Directory For Shopping Details.
Video: Producer: Amanda DiMartino; Director of Photography: Jean Denegar; Editor: Shirley Cheng
‘Do You Know Her’: Director/Producer: Amanda DiMartino; Director of Photography: Ryan DeVita; Gaffer: Shaleyn McGovern; Sound: Xiao Han; Production Assistant: Alana DiMartino; Editor: Chris Davies; Motion Designer: Josh Walker; Entertainment Director: Andrea Cuttler.