20 Stunning Vintage Photos Of Winona Ryder
So many kids who grew up in the late ’80s and early ’90s will attest that the first crush they had was on Winona Ryder. While she’s certainly beautiful, that had just as much to do with the smart, sarcastic, yet warm and slightly awkward persona that made her stand out.
Whether those lovelorn kids shared a similar taste for the macabre as Lydia Deetz in Beetlejuice or felt the frustrations of Veronica in Heathers, it’s clear that Ryder made an unforgettable impact on them.
An Accomplished Woman By The Time She Became One
This photo was taken in 1990, which was less than a year after Ryder’s 18th birthday. Nonetheless, she had already appeared in some of her most fondly-remembered classics by then.
While Heathers wasn’t a success upon release, its cult following has grown so strong as to spawn an acclaimed off-Broadway musical. She had also secured her breakout role as Lydia Deetz in Beetlejuice by then.
Her Momentum Was Red-Hot In 1990
Yet, while her late ’80s work has certainly found its audience, one could argue that an even bigger hit started the next decade off for her. Although Mermaids with Cher and Christina Ricci is also fondly remembered, she hit really big once she worked with Tim Burton again.
That’s because that was the year Burton completed Edward Scissorhands, a touching yet unconventional love story that captured the hearts of audiences and critics alike.
A Keen, Adventurous Eye For Style
Although Ryder didn’t always favor the dark aesthetics of some of her signature characters, she nonetheless pulled punky and gothic styles off very well.
For instance, the way she combined her hairstyle with this leather jacket and sunglasses brings Trinity from The Matrix to mind despite Ryder rocking the look nine years before that movie came out.
A Woman Of Multitudes
Although there was an undeniable coolness to the way Ryder dressed and carried herself, emphasizing that aspect of her aesthetic doesn’t quite cover the extent of her appeal.
As her more wholesome aesthetics in Edward Scissorhands demonstrated, Ryder’s expressive eyes and earnest persona also made her come off as adorable and sweet.
A Moment Of Quiet Before A Whirlwind Period
Although Ryder would soon get very busy in the early ’90s, 1991 — when this photo was taken — was a time of relative quiet for her.
As it turned out, the only release she was involved with that year was the anthology movie Night On Earth, which compiled five dramatized taxi conversations in the world’s major cities. Ryder’s segment took place in Los Angeles, where she played a character named Corky.
Pulling Off Unconventional Fashions
In addition to embracing some alternative, counter-cultural styles, Ryder also took her keen but unorthodox eye for fashion to clothes that fit right in at gala events.
As this 1991 photo demonstrates, this meant mixing and matching pieces that go with different outfits to create an entirely new look. Between the color and cut of the clothes she mixed together, it was clear Ryder knew exactly what rules to break.
Ryder Knew What Was Going On In The Underground
Although Tom Waits grew enough of a cult following to find both his music and himself in major film releases by the 2000s and 2010s, Ryder showed her refined alternative tastes by wearing her fandom for him in 1991.
Once again, she made a simple outfit work so well, especially since she’s already shown how good she looks in leather.
An Unusual Fact About Her Life
When 1992 loomed, Ryder would find herself in another high-profile role, this time in a movie helmed by legendary director Francis Ford Coppola. Since this time period also saw him direct The Godfather Part III and Jack, it’s fair to say his career wasn’t at a high point.
Nonetheless, it seems Ryder lucked into one of the few bright spots in Coppola’s ’90s output, as she played Mina in Bram Stoker’s Dracula. Although she and Keanu Reeves were never romantically linked, the presence of a genuine Romanian priest during their wedding scene may mean they were technically married.
A Serious Feather In Her Cap
In 1993, The Age Of Innocence would see its release and would be so acclaimed as to receive five Oscar nominations. It won one of them for costuming.
However, this film was also a major step forward in Ryder’s career, as her portrayal of May Welland earned her the first of her Academy Award nominations. In this case, it was for Best Actress In A Supporting Role.
The Beginning Of A Busy Year
Although The Age Of Innocence was the most acclaimed movie Ryder was in that year, it wasn’t the only one.
Alongside a quirky, uncredited appearance in a Soul Asylum music video that saw her play a bearded assassin, Ryder also joined a heavy-hitting ensemble cast for the movie The House Of The Spirits.
Another Big Year For So Many Reasons
In 1994, Ryder’s career was hitting a fever pitch, as she would star in two different movies that boosted her career in different ways. That year also saw her guest star in an episode of The Simpsons, where she played Lisa Simpson’s intellectual rival, Allison Taylor.
Meanwhile, Reality Bites cemented Ryder’s appeal from a hip, counter-cultural perspective, while her portrayal of Jo March in Little Women brought her even more prestige from the industry. After all, it garnered Ryder her second and final Oscar nomination to date.
An Honorary Member Of The Alternative Nation
The early ’90s saw alternative rock explode in the mainstream to an unprecedented degree, which made labels scramble to sign any band that Kurt Cobain mentioned liking.
However, it seems it would have been just as effective for these labels to ask Ryder what she liked. For instance, this photo shows her enjoying a performance by Liz Phair and Beck at McCabe’s Guitar Store in 1993. That was not only before Beck hit it big, but just as Phair was releasing her most acclaimed album.
Ryder Made Short Hairstyles Look Fantastic
Throughout the ’90s, it became a lot less unusual for female celebrities to start rocking pixie cuts and other short hairstyles. Granted, a similar trend had taken hold in the ’60s as Twiggy, Audrey Hepburn, and Mia Farrow all made similar hairstyles iconic.
Yet, alongside veteran stars like Demi Moore, Ryder was one of the most prominent figures leading the charge in bringing the simple yet cute look back after the voluminous hairstyles of the ’70s and ’80s.
The Mid-’90s Were A Mixed Bag For Her
Ryder aimed for similar prestige as Little Women in the 1995 film How To Make An American Quilt. Although it was ignored by the Academy and the Hollywood Foreign Press, the cast was nominated for a Screen Actors Guild award.
Although the following year would see her play Abigail Williams in a film adaptation of Arthur Miller’s The Crucible, it also saw Ryder star in the maligned film Boys.
Her Unfortunate Involvement In Two Disappointments
On paper, Ryder’s next career moves in 1997 and 1998 would have seemed enviable. Not only would she be joining the legendary Alien franchise while Sigourney Weaver was still involved but she’d work with respected filmmaker — at the time, anyway — Woody Allen the following year.
Unfortunately, Alien Resurrection didn’t prove any more electrifying to Alien fans than the series’s third instalment did and Allen’s film Celebrity is largely considered one of his more forgettable works.
A Still-Beloved Movie To Close Out The Decade
While the late ’90s introduced some turbulence to Ryder’s career, she ended the decade off strong by co-starring with Angelina Jolie in the coming-of-age mental health drama Girl, Interrupted.
This was a serious passion project for Ryder, as she had acquired the rights to the original book and had tried to get the movie made for years before it was finally released in 1999.
A Bizarre Scandal That Hampered Her Career
Although Ryder’s career couldn’t be hotter in the ’90s, some may recall that it was a lot more understated in the 2000s. The focus was more on independent projects than big blockbusters.
This may not have been entirely by choice, as an unusual incident that saw Ryder arrested for shoplifting $5,000 worth of designer goods from Saks Fifth Avenue in Beverly Hills put her name in the news for all the wrong reasons in 2001.
Some First Initial Swings That Didn’t Work Out
Although the shoplifting incident certainly hurt Ryder’s career, that damage didn’t take place overnight. Indeed, she would have significant roles in two major releases in 2002, the Adam Sandler comedy Mr. Deeds and the artificial intelligence satire S1m0ne.
It’s true that Mr. Deeds turned out to be profitable, but S1m0ne was a pretty serious flop and neither were particularly acclaimed.
Smaller But Not Necessarily Worse Movies
After these 2002 releases, Ryder’s career led her to the independent market. Although she was partially licking her wounds in this period, she also found herself in some films that have now become cult favorites.
Perhaps the greatest of them was the ambitious Richard Linklater adaptation of Philip K. Dick’s A Scanner Darkly. It was made with a sophisticated version of the rotoscoping animation technique and saw Ryder reunite with Reeves in a story of addiction and increasingly dystopian law enforcement.
Ryder Came Back Before The Decade Ended
By 2009, the stigma on Ryder’s image had largely abated, as she was able to secure roles in the blockbuster Star Wars reboot and join the cast of the Oscar-nominated Darren Aronofsky film Black Swan the following year.
However, the role that would later rocket her right back into prominence was Joyce Byers in the enduring Netflix smash hit series Stranger Things. That made the 2010s far kinder to her than the 2000s.
