Your guide to Winona Ryder, one of the coolest people ever (2025)

As a poster child for 90s cult classics, Winona Ryder built a reputation for playing goths, kooks and all-round outsiders. Personal difficulties and a run-in with the law caused her career to momentarily falter, yet she returned and continued in critically acclaimed productions, most recently in the latest Netflix-own series that is set to follow her previous projects as a dark classic. As most in her position can sympathise, Ryder has born the brunt of intense media scrutiny, though her celebrity status is paralleled by an off-kilter reputation for low-key or oddball roles. She’s had her fair share of the typical leading lady scripts that an actress of her calibre inevitably undertakes throughout an A-list career, but her most memorable turns have been for indie films, cult classics, or as one of Tim Burton’s weirdo characters. Because of this, her charm is an imperceptible quirkiness that she carries into her films time and time again. In an attempt to pin down a career that has so far spanned alien encounters, levitation, blood sucking and countless run-ins involving the undead, here is your dA-Zed guide to the Netherworld she inhabits:

A IS FOR AQUAPHOBIA

When she was 12-years-old, the trauma of a near-death encounter in which Ryder almost drowned, understandably triggered a lifelong phobia of water. As a result, her underwater scenes in Alien: Resurrection (1997) were an obstacle, requiring many sequences to be repeatedly re-filmed. Even more traumatically for her, these allegedly had their own complications as one of the scenes went wrong during filming, causing another close call.

B IS FOR BEETLEJUICE

...Beetlejuice, Beetlejuice. Released when Ryder was only 16, her big break came in the stripey-tights form of Tim Burton’s Oscar-winning 1988 supernatural fantasy classic. Her most memorable scene, levitating by the stairs in a mime-along to ‘Jump in the Line’ by Harry Belafonte, sticks in the mind as an iconic moment in her early career, although the film alienated her from her school peers at the time. “I did Beetlejuice, and it was a big movie, but it didn’t help my high-school experience. In fact, it made it worse. I was a freak and a witch,” she told The Cut. Word of a sequel has been circulating for years, and The Geffen Film Company had a script for Beetlejuice Goes Hawaiian in their possession for a long while. Thankfully, the “German Expressionism”-inspired story has never made it to the screen but, in recent months, hopes of a resurrection in the form of Beetlejuice 2 havebeen confirmed by both Tim Burton and Ryder herself. Prepare yourselves for another trip to the Netherworld.

C IS FOR ‘CRIME OF THE CENTURY’

Ryder was arrested on the 12th December 2001, accused of stealing thousands of dollars’ worth of accessories and designer clothes from Saks Fifth Avenue in Beverly Hills, California. The backlash from her convictions caused her career to take a nosedive, leading to Ryder’s short career hiatus. Her recent return to the limelight in Stranger Things has led to her opening up about the incident, with her stating it was hardly the “crime of the century” – especially considering that, on balance, there were new stories far more pressing than hers back in 2001.

D IS FOR DR TIMOTHY LEARY

Dr Leary, the psychologist and advocate of LSD’s potential for use in therapeutic medicine – and prominent figure of 60s counterculture – held ties with Ryder through one of the members of his research team. As it turns out, his archivist, Michael Horowitz, was Ryder’s father. When she was born, Dr Leary went from being the godfather of LSD, to Ryder’s real-life godfather.

E IS FOR EDWARD SCISSORHANDS

Her second run-in with Tim Burton came in the form of the love interest to Johnny Depp’s titular oddball character in this fantastical, tragic love story. Ryder played Kim Boggs, the object of Edward’s affections in a case of art which would later be imitated in life (skip briefly to J for more on this). The pair’s performance delivered us one of the most heartbreaking – and criminally underrated – romantic movie quotes ever: “hold me”, “I can’t”.

Your guide to Winona Ryder, one of the coolest people ever (2)

F IS FOR FRANCIS FORD COPPOLA

Directorial heavyweight Francis Ford Coppola, of The Godfather and Apocalypse Now fame – as well as father of The Virgin Suicides director Sofia – cast Ryder as Mina in his 1992 adaptation of Bram Stoker’s Dracula. She took on a dual part as both the ethereal, reincarnated love interest Mina Murray, and Elisabeta, one of Dracula’s previous partners. The film earned three Oscars, and it was in fact Ryder who initially brought the script to Coppola’s attention after withdrawing from a part in The Godfather III.

Your guide to Winona Ryder, one of the coolest people ever (4)

G IS FOR GIRL, INTERRUPTED

Loosely adapted from Susanna Kaysen’s autobiographical novel of the same name, this 1999 film saw Ryder’s turn as its authorial character who suffers a nervous breakdown and, following an attempted suicide, is subsequently checked into a psychiatric hospital, alongside patients played by Angelina Jolie, Brittany Murphy and Elisabeth Moss. While it may have garnered a pretty dismal rating on Rotten Tomatoes, it earned Ryder’s co-star Angelina Jolie (playing a manipulative, charming sociopath) an Academy Award, a SAG award and a Golden Globe. You may well be familiar with its accolades, given the commercial success of the film, but what you may not know is that Ryder was one of the production’s Executive Producers.

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H IS FOR HEATHERS

Ryder is well-known for her role as Veronica Sawyer in this film (more on that later), but struggled to secure the part to begin with. In an interview with Dazed 100 star, Tavi Gevinson, she explained how her original audition was met with despondency: “I was not the first choice for Veronica in Heathers. I auditioned and they were like, "Oh, thanks." And I went to the Beverly Center to Macy's and had them do a makeover on me.” Astonishingly, it was her looks that she reckons were preventing her from securing the part, “I went back because I kind of knew that they thought I wasn’t pretty enough. They were trying to get Jennifer Connelly.”

Your guide to Winona Ryder, one of the coolest people ever (8)

I IS FOR INDEPENDENT LENS

During its series runs, each week the Independent Lens on US television showcases a selection of documentary and short fiction films. In 2004 came the documentary that Ryder co-produced and co-narrated alongside Tim Robbins. The Day My God Died documented the international child sex trade, detailing the stories of Nepalese girls sold into that world. It visits Bombay’s brothels and is, as you might expect, harrowing and poignant; certainly worth a watch.

J IS FOR JOHNNY DEPP

Her “first everything”, Ryder and Depp were together for almost four years between 1989-1993 and engaged for three of those. Their relationship coincided with a period of intense media scrutiny on her life both personal and professional, similar to the tabloid attention she received at the time of her run-in with the law (see S). He had her name tattooed on him during their relationship, opting to have “Winona Forever” inked on his arm – after they broke up, he had it changed to “Wino Forever”.

Your guide to Winona Ryder, one of the coolest people ever (10)

K IS FOR THE KILLERS

Once again cast in a topsy-turvy Tim Burton project, this downright bizarre video for mid-noughties pop-rock band The Killers and their track, ‘Here With Me’, sees Ryder’s turn as the object of an adolescent boy’s dark, twisted fantasy. Of course, given who directed it, Ryder’s character in the video isn’t your average one-dimensional love interest; there’s no lighthearted seduction and twerking hadn’t made it into common lexicon back then. Instead, Ryder is (literally) cast as a semi-animated waxwork doll – blonde wig, wick and all. Somehow it does get weirder towards the end, when her wig is removed and her boyfriend (spoiler, also a human candle), very much lights her fire by igniting the bit of string on her head. It’s The Killers in their ailing years, but kind of fun as a spectacle.

L IS FOR LITTLE WOMEN

Louisa May Alcott’s autobiographical novel, set in post-civil war USA, tracked the coming-of-age of four sisters and has been adapted for the silver screen four times. The most recent, in 1994, saw Ryder take the lead role as tomboy, Jo. Weirdly, it was marketed as a Christmas film, and released on 25th December; probably due to the classic family vibes. Her co-star siblings in the film were played by Kirsten Dunst, Claire Danes and Trini Alvarado, with Susan Sarandon playing their mother and Christian Bale as the boy-next-door. It gained good reviews and earned Ryder an Oscar nomination.

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M IS FOR MERMAIDS

In 1990, Ryder played angsty teen Charlotte, daughter of Rachel –played by Cher – and sister of Kate (Christina Ricci). The film was an adaptation of Patty Dann’s novel of the same name, and because of its 60s setting, had a stellar soundtrack and featured some extremely retro hairstyles. There were no actual Mermaids involved – most of the characters simply had an affinity of some sort with water – and fortunately for Ryder and her predilection against anything aquatic, no underwater scenes were required.

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N IS FOR NETFLIX

If you haven’t binge-watched the entire series of Stranger Things yet, you’re probably holed up in a high-security government testing facility. In the new Netflix series, we observe Ryder’s panicked terror as the mother of a missing son, complete with all the tropes of a 70s horror/thriller. It cements her metamorphosis from waifish teen to a mother figure and thankfully is set to return for another series.

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O IS FOR OPPORTUNITIES

We often hear about the roles that actors turn down or those that are given to someone else. It usually transpires that we couldn’t possibly imagine a character being played by anyone other than the actor who eventually landed the part. In Ryder’s case, she reportedly turned down Sleepy Hollow, the part going to Christina Ricci instead; was considered for Helena Bonham Carter’s role in Fight Club; auditioned for Rose in Titanic, and was cast as Michael’s daughter, Mary Corleone in Godfather III but had to drop out due to illness, being replaced by the director’s daughter, Sofia Coppola.

P IS FOR PERSONAL STRUGGLES

As she has spoken more of the reasons for, and fallout from, her criminal activity, Ryder has given the public a greater insight into the health issues from which she was suffering in the lead up to that incident, and has had to deal with since. She was interviewed in 1999 by Diane Sawyer and later reflected on how her discussing her own mental health during this interview compounded a negative press image of her. “I did Diane Sawyer, and I talked about my experiences with anxiety and depression when I was that age. And I think by doing that, maybe coupled with my physical size, there’s this ‘crazy’ thing. And I’ve realised recently it’s literally impossible to try to change that story.”

Q IS FOR QUACK DOCTOR

Understandably, Ryder has remained relatively tight-lipped about the events surrounding her criminal conviction, due in part to her bowing out of the limelight and the ensuing quieter years of her career. Eventually breaking the self-imposed silence in 2007 and speaking on her more troubled times, she stated that she was the unfortunate patient of a doctor with questionable medical qualifications who presided over her treatment for a broken arm. When discussing her conviction for grand theft, she explained that “two months prior to that, I broke my arm in two places, and the doctor, a sort of quack doctor, was giving me a lot of stuff and I was taking it at first to get through the pain. And then there was this weird point when you don't know if you are in pain but you're taking it.”

R IS FOR RAINBOW

As a harbinger of sorts for the kooky roles Ryder has become known for, her childhood was equally off-beat. Ryder – full name Winona Laura Horowitz (Ryder was adopted in tribute to soul and rock singer, Mitch Ryder) – and her family relocated to a Californian commune known as the ‘Rainbow Commune’ when Ryder was seven. They were there with seven other families in order to live off the land as a self-sufficient group, cut off from modern amenities; a time which Ryder has reflected upon fondly. “It was pretty incredible. We were in 380 acres of redwoods and there was no electricity.” It was during this period that Ryder became interested in the idea of acting, unsurprising given her parents’ bohemian outlook and friendships with author Aldous Huxley and poet Allen Ginsberg.

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S IS FOR SUPERFANS AND STALKERS

It seems almost par for the course these days for celebrities to experience hounding from fanatical fans, and Ryder is no exception. “I’ve been called a cunt to my face by someone who was just saying they were a fan. I was with my parents having dinner.” Charming. Expletives aside, she’s dealt with stalkers, too, as she told NY Mag. “I had a few. One was really nice. He kept showing up as an extra on movies, and you don’t know. You have to be careful. So I told the director, because he was kinda creepy. And I got this letter in my trailer the next day that was like, ‘I was just trying to get work as an extra! Just so you know, I’m not even obsessed with you anymore, I’m obsessed with Alyssa Milano now!’ So he kind of left me for Alyssa Milano.”

T IS FOR TCHAIKOVSKY

In 2010, Black Swan, the story of Nina, a ballerina (Natalie Portman) who suffers a gradual decline in her psychological wellbeing as she trains for the lead role in Tchaikovsky’s Swan Lake ballet, was released to critical acclaim, earning an Oscar for Portman. Ryder played the role of Beth Macintyre, the former darling of the ballet company, now being pushed out by Portman’s younger counterpart. Her character delivered some bitter jibes to Nina, so much so that Ryder wrote to Portman afterwards to apologise, "I wrote (to) Natalie and I got her something when I had finished filming, saying, 'I'm so sorry I had to say all those horrible things.'"

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U IS FOR URI

Named after the first man in outer space, Russian cosmonaut Yuri Gagarin, Ryder’s younger brother Uri was responsible for her participating in one of her most successful film franchises. Uri was a huge Alien fan, and so when Ryder was asked to get on board with Alien: Resurrection, it was her brother’s fanaticism that swayed her decision, leading to her taking on the role as Call. She’s been quoted as saying that she “didn’t care if I died on the first day of filming”, taking the part before reading the script on the basis that it would give her bragging rights over her brother.

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V IS FOR VERONICA SAWYER

Heathers (1988) saw Ryder’s star rise in the world of indie film, and it was her character, Veronica Sawyers, that continued her affinity for playing dark characters. The flick was an up-turned high school teen film that showed cliques turning sour, and the project catapulted Ryder to cult success. A little like an earlier, macabre version of Mean Girls, Ryder’s character would be the equivalent of Lindsay Lohan’s Cady Heron, only instead of replacing face cream with foot cream, she masterminds several murders.

W IS FOR WALK OF FAME

Hollywood’s famous promenade isn’t reserved for building politically-charged mini concrete walls around pavement slabs dedicated to presidential candidates. In 2000, Ryder was lauded for her acting achievements with her own star on the Walk of Fame. It seems that, in spite of her successes, the tribute came as a surprise to her. During the star ceremony, she told reporters “When I hear about this, I thought it was a joke… [it] gives me a chance to say you can walk all over me.”

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X IS FOR GENERATION X ICON

It might be crap being a millennial, what with Brexit, crippling student debts, and no chance of moving out of your parents’ house. Your closest neighbour in this respect is the Generation X kids, those disaffected youths of the 70s and 80s, and babies of the baby boomers. Ryder is considered somewhat of a poster child for this generation, a reputation reinforced by the ambivalent roles she’s tended to take. Her role in 1994’s Reality Bites, directed by Ben Stiller, is considered as one such film, as it showcased the lifestyles and careers considered typical for the disenfranchised generation.

Y IS FOR YEARS OUT

During her career hiatus, Ryder spent time away from acting by moving to stay with her parents in San Francisco. In an interview on this period, she explained that she did so in order “to take a break, be home for a while and explore some other interests that I would have explored if I hadn’t become an actress.” These interests could not be further away from her day job: a fascination with constitutional law drove her to sitting in on lectures at Berkeley College, while she also paid a visit to Julia Butterfly Hill, a life coach and environmental activist who spent 738 days living in a 1,500-year-old redwood tree. “I climbed 180ft up to where she was but I only lasted six days up there – she lasted nearly two years.” Luckily for us, she returned to acting after a short while.

Z IS FOR ZOOLANDER

“There’s more to life than being really, really, ridiculously good looking.” Zoolander underwent a major high-fashion comeback last year with the release of Zoolander 2, gaining its own Vogue cover and an enormous celebrity cast list. Back in the original, Ryder made her own cameo appearance as a wide-eyed flirt, complete with co-ord red lipstick and vest top (red means desire, duh). Beguiled by Ben Stiller’s blue steel charm, her character tries desperately to win over his affections, ultimately in vain as he brushes her off with “I gotta go pee”. We’ve all been there.

Your guide to Winona Ryder, one of the coolest people ever (27)
Your guide to Winona Ryder, one of the coolest people ever (2025)

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