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EVERY GIRL WANTED TO BE HER AND EVERY BOY WITH HER. THE ELFIN BEAUTY REIGNED SUPREME – THE BEST ROLES, THE BEST MEN AND A STYLE ALL HER OWN...
Winona Ryder embodied a generation. In an era saturated with Boys II Men lyrics, Brendan Walsh life lessons, Baywatch tans and Steve Erkel comedy she presented a glimpse of reality. Ryder fused the beauty of Audrey Hepburn with the angst of Kurt Cobain. She rebelled against the Hollywood starlet ideal, donning her alabaster skin, vintage threads, pixie haircuts and matt-red lipstick. A beacon of cool long before magazine journalists knew how to spell Chloë Sevigny, Lou Doillon or Karen Orzolek, Ryder became the girl every teenager in the ‘90s wanted to be. Choosing protests over Prada, Chaucer over Cosmopolitan and merit over money she made intelligence sexy and being awkward, beautiful.
“I’m not going to think about my future, because it’s just going to stress me out”, (Winona Ryder, 1987). While Ryder’s elfin-like face initially landed in our living rooms via the unforgettable Beetle Juice in 1988, her film career actually began two years earlier when the then 14-year-old won the part of Rina in Lucas. Against the where-are-you-now collective of Corey Haim, Charlie Sheen and Courtney Thorne-Smith, Ryder shined as the unrequited love interest of Haim’s character, Lucas. Interviewed for the San Francisco Chronicle in 1986 Ryder brazenly suggested, “[Lucas] is about real stuff. I think that’s why people like it. I mean, hasn’t everybody at some time fallen in love with a person who doesn’t even acknowledge their existence?”
Failing to acknowledge Ryder’s existence was virtually impossible by the start of the ‘90s following the release of cult classic, Heathers, in 1989. The original Mean Girls, Heathers crossed into previously un-chartered territory, merging the genres of suspense, comedy and drama to create a high school flick that attracted as much controversy as it did praise. With such memorable lines as “Fuck me slowly with a chainsaw” and “Grow up Heather, bulimia’s so ‘87”, Heathers instantly attracted an audience of disengaged youth and, not surprisingly, an onslaught of protests from religious and parental factions. Disobeying the orders of her own parents as well as her agent, Ryder chose to partake in the film, uncannily predicting its future cult status.
“[My character] Veronica Sawyer became my new role model,” admitted Ryder in an interview with the Los Angeles Times. “I felt like – if I don’t do this movie – I’ll never be able to live with myself and I’ll ‘kill’ whoever does do it!” Joining forces with J.D. (played by ‘80s heart-throb Christian Slater) Ryder’s character is responsible for knocking off, one by one, a clique of rich girls named Heather, masking each crime as suicide. Highlighting previously taboo subjects such as bulimia, suicide and rape within the course of a comic teen-flick resulted in public outcry upon its release. “Of course [the script] was exaggerated, but it did ring true. There are sadistic cliques that thrive on humiliating other people,” Ryder said in an interview with The Face. “Kids are weird, they’re wacked, but it’s not their fault, it’s society. They think the ultimate thing you can be is a movie star... it’s just total bullshit. Most movie stars - especially the young ones – are just fucked up... it bums me out...”
The daughter of intellectuals Michael and Cindy Horowitz, and god-daughter of LSD king Timothy Leary, Ryder was well informed on where and how to draw the line. Despite starring alongside a plethora of coke-snorting child actors Ryder saw no appeal in signing up to the pre-rehab lifestyle. “I don’t do things that are harmful to me,” Ryder told The Los Angeles Times at age 17. “I’ve experimented with stuff... But curiosity is one thing. Destroying yourself is something else.” Rather than shove something up her nose, Ryder put her nose into books, art, music and scripts that offered something original. “Heathers taught me a lot about what I want to do with my life [and] my career,” Ryder said in her first interview with Rolling Stone, “Which is to never do anything I don’t feel 100 per cent about...”
Within a year, Ryder had risen from a teen newcomer to adult star, taking the lead roles in three consecutive box office hits – Mermaids, Welcome Home, Roxy Carmichael and Edward Scissorhands. Cementing herself as the style icon of the ‘90s generation, Ryder’s face began decorating the covers of America’s best-selling glossies while her black humour and literary wit saturated features in cutting edge UK publications. Ryder was socially aware, undeniably talented, universally attractive and irrefutably real. She may still have been a teenager, but in the five years following her first feature film, Ryder had single-handedly removed the idea that teen actresses were devoid of substance, raised the bar for young celebrities and granted the youth of the ‘90s a voice. She also won the heart of none other than ‘90s superstar, Johnny Depp.
Catapulted onto global tabloid covers via the ever-watchful eye of the paparazzi lens, Ryder’s relationship with the 21 Jump Street star brought her celebrity status to an entirely new level. She was no longer simply the stylish thrift-shop dresser who had landed roles in every other Hollywood hit. “It’s like a mosquito, it’s annoying,” said Ryder of the intense scrutiny of her relationship. “But you can’t pay too much attention, because it’s too tiresome.”
If Ryder was the face of the ‘90s, then Reality Bites was the film. With a script that could be lip-synched by any teenager in the West, Reality Bites fused every element of youth culture – grunge, drugs, sex, relationships, music, art and technology – to create something spectacularly original. And, at the centre of the magic was Ryder; the poster girl for the vintage-dressing-socialist-writer. Alongside Ethan Hawke, Janeane Garofalo and Ben Stiller, Ryder flawlessly portrayed the average middle-class freshman, complete with high hopes and an empty bank balance. By starring in Reality Bites Ryder had effortlessly moved with her audience from teen to young-adult. She had grown-up, into her own skin, style and self.
By the late ‘90s Ryder had clocked up nearly 30 feature films including Little Women, The House of the Spirits, Night on Earth, The Crucible, Alien: Resurrection, How to Make an American Quilt and The Age of Innocence – the latter earning her an Oscar nomination. “I’ve been really lucky,” she said in The San Francisco Examiner. “I can count on one hand the actors who have survived going through adolescence on screen.” As well as survive adolescence Ryder survived a number of public heartbreaks after ending relationships with Depp, Beck, David Duchovny and Soul Asylum’s Dave Pirner.
In 1996, fresh from her break with Pirner, Ryder hooked up with Hollywood newcomer, Matt Damon, after being introduced at a New Year’s Eve party by her then bestie, Gwyneth Paltrow (who was coincidentally dating Damon’s bestie Ben Affleck). The cool version of today’s Sophie Monk and Nicole Richie, the duo were snapped around town with and without their partners. Dressing head to toe in designer outfits and finishing off each other’s sentences, Ryder and Paltrow became in themselves one of the power couples of the late ‘90s. Ryder then starred in Girl, Interrupted in 1999. It was a part for which Ryder should have been granted an Oscar, instead it was overshadowed by the future face of the new millennium, Angelina Jolie. For many it was the beginning of the end for Ryder; the start of a decade that would see her lose Damon to Penelope Cruz, gain bit parts in bad sitcoms, star alongside aging actors in pathetic romances (does anyone remember Autumn in New York?) and perhaps most of all, see her labelled as a loony after shoplifting from Saks Fifth Avenue.
“I’ve learned that it’s OK to be flawed, that life can be messy, that some days you glide and some days you fall, but most important, that there are no secret answers out there,” (Winona Ryder, 2001).
There is one role every teen in the ‘90s will remember Winona Ryder for playing – herself. Against a backdrop of power-hungry, coked-up celebrities she was the normal, if slightly quirky girl you wanted to befriend. She wore second hand clothing in an era saturated by brands, she read J.D. Salinger while her peers read Judy Blume and, in an age when the famous knew it all, Ryder admitted to knowing “not much”. She chose interesting films that pushed the boundaries of social commentary and she dated the kind of boys that remain to this day at the forefront of underground cool. Philosophical without being patronising and intelligent without being intimidating, Ryder epitomised the hopes, frustrations and fears of her generation. She truly was the face – eyes, ears and voice – of the ‘90s.

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