Winona at 50

On October 29, Winona Ryder turns 50 years old. (Fifty!!) To anyone who was a teen or older in the late ’80s and early ’90s this seems unfathomable. Winona couldn’t possibly be the age our mothers were when we were living in her world. It feels wrong. Winona was always the young girl with the old soul. The cool kid everyone wanted to hang out with but who preferred to hang out with the bullied, the weird, the strange and unusual. The girl who probably knew more than you did, but didn’t rub it in. Even her name was out of the ordinary: Winona (after the city she was born in), Ryder (picked as her stage name because her father liked the singer Mitch Ryder). An instantly recognizable single name. Garbo. Marilyn. Winona. Then there was her background: the commune without television. The 4.0 GPA. Timothy Leary as her godfather. Family friends Allen Ginsberg and Philip K. Dick. Aldous Huxley’s wife. Winona was always going to be something unique. A once in a lifetime star, destined to burn out in a blaze of glory.

And what a blaze! I can’t think of any other living actor who managed to churn out so many iconic roles and films at such a young age and in such a short time. In only six years, from 1988 to 1994, Winona starred in a deluge of greatest hits which generations to come would worship—often at the Instagram altar of throwback photos, wardrobe, quotes and attitude. Beetlejuice, Heathers, Mermaids, Edward Scissorhands, Night on Earth, Bram Stoker’s Dracula, The Age of Innocence, Little Women and Reality Bites—by which time, She had worked with such luminaries as Tim Burton, Jim Jarmusch, Francis Ford Coppola and Martin Scorsese; gotten top billing over the likes of Ethan Hawke and Ben Stiller; proven herself to be a good dramatic actress—going so far as to give the best performance of anyone involved in The Age of Innocence including, yes, Daniel Day-Lewis and Michelle Pfeiffer (not exactly featherweights); and earned herself two Oscar nominations. And she was still only 22 years old. TWENTY-TWO! 

“In only six years, Winona starred in a deluge of greatest hits which generations to come would worship.”

Winona was a bona-fide bankable movie star in an era when that actually meant something. Helen Childress, screenwriter of Reality Bites, which, love it or loathe it, is the most quintessential Gen X movie ever made, once said she had written the role specifically with her in mind—because there simply were no other actress at that moment in time; there was only Winona. As the old adage goes: girls wanted to be her (and dress like her, hang out with her) and men wanted to be with her (and sometimes dress like her and hang out with her). She was exceptionally beautiful, had great comic timing, and incredible style in an era before stylists. She could be goth and a little punk; simultaneously old-fashioned and incredibly modern; and looked just as much at home in jeans and a tee-shirt as she did in a full-blown Victorian corset. Yet, through it all, she seemed unaffected and oddly approachable. 

Maybe it was that blatant no-fucks-given attitude that made her so cool. In an era where everyone was cloying over Carson, Letterman, and Leno, Winona chose not to appear on talk shows. When every actress was being asked to gratuitously take off their clothes, she didn’t do nudity. She didn’t revel in celebrity and tell gossipy anecdotes, have public feuds, or reveal tidbits about her private life. She never came off as hungry. Of course, she was young and couldn’t run from her fame completely—dating Johnny Depp was certainly tinder to the tabloid spark, but never enough to distract from her memorable characters. Think of the stars, male or female, from that period—and now think of how many of their performances are still a part of the culture the way Veronica Sawyer and Lydia Deetz are. Tough to do, isn’t it?

Winona continued to work consistently through the rest of the decade, but her choices somewhat plateaued before dropping out of sight. Even 1999’s Girl, Interrupted, which could be marked as the last film of the true Winona Era, doesn’t hold up to her earlier films. It was around this time things started to change. Winona had optioned the Susanna Kaysen memoir herself, championing it as her ultimate passion project, and even coming on as Executive Producer. Although reviews were decent, it was relative unknown Angelina Jolie who stole the show and swooped up an Oscar, ushering into the world a new rebel—this one much more of an enfant terrible (tattoos, vials of blood, et al.) than Winona ever was —and with it, a new era.

“How many performances are still a part of the culture the way Veronica Sawyer and Lydia Deetz are..?”

Maybe it was the times, maybe it was her battle with depression and insomnia and other ailments which come with being too famous too young. Maybe she was just burnt out. In 2001, Winona was caught shoplifting from Saks Fifth Avenue, and thereafter, seemed relegated to small roles and even smaller indie movies. It wasn’t quite “movie jail,” where Demi Moore and Meg Ryan have been languishing with life sentences (indeed, the world is cruel to actresses of yore)—but she didn’t seem to have a place in this new millennium. How could she have? How could anyone who didn’t even stoop to go on chat shows navigate this world of Facebook, Twitter, and Instagram? (To this day, Winona has no social media accounts.) With constant access to celebrities and their everyday lives, the magic of stars is forever diminished. And what would Winona be if not for a little touch of magic, singing Harry Belafonte, floating at the top of the stairs? 

Had she retired back in ’94 (or even ’99 when she was still only 27), Winona Ryder would probably be remembered as the greatest star of her generation, bar none—which she probably is. But Winona didn’t die young on the steps of The Viper Room and guarantee herself a place on the legends table; or become a recluse and disappear into seclusion, as seemed her fate. Instead, she went against the obvious as she always had, and continued to work and live and do normal things. And it turned out she WAS human after all, aging like the rest of us and making mistakes and questionable choices and trying to adapt to the new world of instant gratification and streaming services. And suddenly, it was fifteen years later, Beetlejuice and Heathers were both being turned into stage musicals, and Winona was making a comeback on Netflix’s hit series Stranger Things. Admittedly, it felt odd to see Winona playing a mom to two teenage boys, in a period piece set in the era when she herself was making her debut as a teen in love with Corey Haim in Lucas, but it did feel good to have her back. 

Winona, like her characters, has always done things her own way, on her own terms—strange or quirky or not. That’s what made her cool. That’s what made her unique. That’s what made her feel like one of us. Yes, Winona turning 50 feels jarring, but only because it means that we, too, are getting old—and that it really has been 30 plus years since Veronica Sawyer stood at the entrance of Westerburg High and lit a cigarette off the explosion of a suicide bomb (The ’80s, am I right?).

But that’s on us. Mortality is a terrible thing to face, but Winona Ryder is an icon. And icons are immortal.