Winona Ryder has always challenged authority—whether onscreen, playing characters like her vengeance-seeking outsider who offs all the popular kids in Heathers, or off, with that notoriously overblown shoplifting incident, for which she was pilloried by the tabloid press.
Perhaps this sense of rebellion, of not playing by the rules, runs in the family. She is, after all, the goddaughter of activist and psychedelic guru Dr. Timothy Leary, who, in his self-described “user manual” How to Operate Your Brain, wrote, “To think for yourself you must question authority and learn how to put yourself in a state of vulnerable open-mindedness, chaotic, confused vulnerability to inform yourself.”
“Question Authority,” Ryder says, repeating her godfather’s mantra to me at a hotel suite in Downtown Manhattan in her unmistakably fragile, forever-adolescent voice. “This is his watch,” she says, extending her left arm to me and revealing an old black-and-gold timepiece on her wrist. “It’s pretty cool. It’s very Tim.”
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Ryder remembers being 9 years old and watching Leary engage in a fiery debate with G. Gordon Liddy, as well as the days in his latter years, when he’d still dazzle her with his witty anecdotes and rejoinders.“We were very, very close, but in a way that people don’t expect,” she recalls. “He was very much a godfather to me. He helped me with my homework, took me to ballgames. I was never around any drug-taking. In fact, I do remember a few times where people would get kicked out of the house for doing that sort of thing, so he was very protective. He’s one of the most inspiring people that I’ve ever met. I miss him every day.”
Besides the guidance of her influential godfather and her hippie parents, Ryder’s innate sense of distrust and rebellion was amplified by a traumatic incident that befell her in the seventh grade. From the ages of 7 to 10, Ryder grew up on a remote commune—sans electricity—in Northern California with seven other families. At 10, her family moved to Petaluma, California, and in her first week of junior high, Ryder, who back then was a punk rock kid that sported a short haircut in tribute, she says, to Bugsy Malone, was jumped by a group of fellow students.
“I wasn’t just bullied—I was straight-up beat up,” she says. “It was my third day of school in seventh grade in a brand new town, and I had the short hair. I had a hall pass, and there was this gang of kids behind me, both guys and girls, and they were yelling ‘faggot’ at me. I didn’t think they were talking to me, and also, having come from the Bay Area and being around the gay community there, I thought that word was really fucked up. But I really didn’t think they were yelling it at me, and then all of a sudden they came at me. I had six stitches and a fractured rib, and then I got put on home study that year and went to a different school in eighth grade.”There is a silver lining in all of this, of course. “Because of that I’m an actress,” Ryder says. “When you get put on home study you get your week’s worth of work on Monday, and I was a pretty good student—I got straight A’s—so I’d do my week’s worth of work on Monday and then have nothing to do. And my parents, god bless them because we were very poor, they saved up and sent me to ACT [American Conservatory Theater], which I never would’ve been able to attend had I been in school because it was a 45-minute drive, and that’s where I was discovered. So if those kids hadn’t beaten me up I’d have stayed through seventh grade, never gone to ACT, and gotten discovered. It’s kind of crazy.”
It makes perfect sense, then, that Ryder would be starring in Experimenter, an artsy biopic of renowned social psychologist Stanley Milgram (played by Peter Sarsgaard), who conducted a controversial experiment on obedience in the 1960s at Yale. Milgram, who was Jewish, wanted to understand why so many Nazis complied with their horrific orders during the Holocaust, and analyze how far people would go when complying with authority. Ryder, who is excellent in the film, plays Milgram’s devoted wife and secretary, Alexandra.
And the film, directed by Michael Almereyda, holds a special place for the actress formerly known as Winona Horowitz, since many of her father’s relatives were killed during the Holocaust.
“It was a direct response from Nazi Germany, just following orders, and it’s fascinating because one of my grandfathers died in Guadalcanal, and another died in the [concentration] camps,” she says. “So to me, it’s always been a very personal thing. But I think Michael did something amazing in turning the biopic on its head. It’s a true art film, and there are not a lot of filmmakers who can pull that off these days because you have to make compromises.”
I ask her if she was ever in a situation in Hollywood in which she felt like she was complying.
“I’ve been very lucky to not deal with a lot of the Hollywood stuff, and I think a lot of it was not living in L.A. and staying up in San Francisco,” says Ryder. “I wasn’t sexualized as a teenager—not that there’s anything wrong with doing nudity—but I was very protected. A lot of young actors didn’t make it. It’s really sad. I remember I wanted to audition for River’s Edge because I loved Keanu so much—”
“He was pretty dreamy back then,” I interrupt.
“He still is,” she says, visibly swooning. “But there was a sex scene and my parents wouldn’t let me audition for it. So I wasn’t this weird, sexualized being. I was kind of considered in Hollywood to be a bit of a nerd. I just loved to read and watched movies. I never really went out a lot, and just worked. Even if there was anything inappropriate, I wouldn’t have noticed.”
In order to get into the American Conservatory Theater’s youth program, kids had to pick and perform a monologue on tape. Ryder chose her favorite author J.D. Salinger’s Franny and Zooey, adapting it into a scene in which Franny is trapped in a bathroom stall and freaking out. A casting director who was scouting the ACT caught wind of Ryder’s tape, and she was cast as a high school band geek in her feature film debut, 1986’s Lucas.
The indie Square Dance followed, where, Ryder says, she met her “longtime mentors” Jane Alexander and Jason Robards. But it was the next film, as the goth teen Lydia Deetz in Tim Burton’s Beetlejuice, that made her a star—even if it didn’t win her the respect of her classmates.
“Beetlejuice was big,” she says. “It was almost pre-goth, in a way. But we didn’t know that was going to be a big movie at all. And I was in high school when it came out, so I thought I was in this movie and it’s doing things and people are going to be nicer, and they were calling me a ‘witch’ and ‘a weirdo’ and throwing candy corns at my head! It was like I couldn’t win.”
Then she got her revenge in the next film, 1988’s Heathers, a risqué satire on teenage suicide in which she plays a reformed popular girl who, with the help of sociopathic new kid J.D. (Christian Slater), begins offing her popular classmates and framing them as suicides.“I did get my revenge,” she says with a chuckle. “And that was a weird one, too. With Heathers, if you ever watch the DVD commentary, they say, ‘Remember? We didn’t think she was pretty enough.’ I wanted it so bad. I got the script from Michael McDowell, who wrote Beetlejuice, and I’d been calling them all the time. I went to see the filmmakers and they were like, ‘Ehhhh,’ so I went to the Beverly Center Macy’s, got a free makeover, and came back and said, ‘Look—you don’t have to pay me. I don’t care. You just have to cast me in this.’” She laughs. “That was the first time I played a semi-attractive character.”
In Edward Scissorhands, however, she played the town beauty.
“Yeah,” she says, with a shrug and a smile, “although it was such an ongoing joke between me and Tim [Burton] that to put me in a cheerleader outfit and a blond wig was just… I don’t know what I did to deserve that!”
As for Burton’s highly anticipated sequel Beetlejuice 2, which will bring back original stars Ryder and Michael Keaton, the actress says it’s still hopefully happening, but nothing is set in stone. “Tim talked about it finally, but then every time I say something it gets blown up and I feel bad, because the truth is I don’t know where it stands,” she says. “I’m pretty sure it’s happening, but nothing’s official—even just the deals being done. And Tim is such a perfectionist so he wants the script to be perfect, so he may even take another movie before, although I hope he doesn’t!”
For those of us who brave the social media waters, every Thursday, people—mostly younger, some older—share old photos as part of the hashtag #TBT, signifying “Throwback Thursday.” And for a lot of millennials, this means sharing old photos of Gen X icon Ryder, now 43, whether in real life, or in her iconic roles in films like Heathers and Reality Bites.
When I mention the phenomenon to her, she laughs. “Woof! The golden oldies,” she says with a chuckle. “Oh, is that what a ‘Throwback Thursday’ is? I’m not on the social media thing. But people have shown me and I’m like, ‘Oh man, those are old pictures.’”She pauses, losing herself in thought for a moment. “I want to be allowed to get older, but people are very attached to me at this certain time. So with Experimenter and Show Me a Hero, I’ve started to feel more liberated to play my own age—which was tough for me for a while because I sort of look too young, and I’m sure there were other factors involved, but your thirties are tough when you’ve had so much success in your teens and twenties, and people have this idea of you as the girl from Reality Bites, you know? So then people are like, ‘What? She’s a lawyer?!’ Even though I clearly could’ve gone to law school or something like that.”
Another slice of the halcyon ’90s that people are attached to is her tumultuous, intense relationship with ex Johnny Depp. The two met at the 1989 premiere of Great Balls of Fire!, and were engaged from 1990 to 1993. Depp was so in love with her that he had “Winona Forever” tattooed on his arm, and following their split had it altered to say “Wino Forever.”
When I bring up the public’s ongoing fascination with that relationship—as well as the social media sharing of the couple’s photos as a sign of a bygone era—she smiles, and seems to be at peace with it.
“It’s gotta just be the nostalgia, I guess,” says Ryder. “Honestly, I think there were six pictures of us taken and they probably just do the filter thing. I’ve heard that but I can only guess that it’s nostalgia. We were both very young and pretty open about our feelings. We hadn’t learned yet to not share everything with everyone. But now, it’s as if it happened yesterday. I don’t know. With all the social media, it’s a totally different world now.”
