Winona Ryder has carved out her place as Hollywood’s ultimate “weird girl.” From Beetlejuice and Heathers to Girl, Interrupted and Stranger Things, she’s perfected the art of bringing out the inner depth and quirks of characters who feel a little out of step with the world around them. So it makes sense that Ryder herself has some equally fascinating stories—she’s often described herself as an outcast in real life, too.
Born Winona Laura Horowitz and raised on a commune (though she insists it wasn’t a cult), Ryder seemed destined for a life a bit out of the ordinary. And although a notorious shoplifting scandal almost derailed her career, she’s since staged an incredible comeback, winning over fans with that signature offbeat charm. For everyone who’s ever felt like they didn’t quite fit in, and all the “weird girls” who see Ryder as an icon, here are some of the quirkiest, most endearing facts about Winona that make her all the more captivating.
#1. She Was Picked On In Middle School – And Expelled For It
Ryder’s time at Kenilworth Junior High in Petaluma, CA, was far from easy. With her cropped hair and “old Salvation Army suit,” she stood out, making her a target for bullies. Things escalated when a group of girls cornered her in the bathroom and attacked her. Astonishingly, it was Ryder—rather than her bullies—who ended up getting kicked out of school.
Years later, however, Ryder had a memorable moment of poetic justice. In a now-viral quote, she recalls that after her rise to fame, one of the same classmates who’d tormented her came up and asked her for an autograph.
Iran into one of the girls who’d kicked me, and she said, “Winona, Winona, can I have your autograph?” and I said, “Do you remember me? I went to Kenilworth. Remember how, in seventh grade, you beat up that kid?” and she said, “Kind of,” and I said, “That was me. Go f*ck yourself!”
#2. She Didn’t Realize She Was Talking To Tim Burton When They First Met
The first encounter between proud outsiders Winona Ryder and director Tim Burton was as quirky as their eventual collaborations.
While waiting to meet Burton, Ryder struck up a conversation with a random guy she’d met on the studio lot. After 45 minutes, she finally asked, “Where is this Tim Burton guy?” Her chat partner simply replied, “Oh, that’s me.” And just like that, an iconic duo was born.
#3. She Might Have Accidentally Married Keanu Reeves (At Least In The Eyes Of The Greek Orthodox Church)
Winona Ryder and Keanu Reeves starred as Mina Murray and Jonathan Harker in 1992’s Bram Stoker’s Dracula. Years later, Ryder revealed a surprising detail about the film’s production—one that might mean she and Reeves accidentally got married for real. For their characters’ wedding scene, director Francis Ford Coppola hired an actual Greek Orthodox priest and had him perform the entire ceremony on set.
Though no paperwork was signed, meaning it wasn’t legally binding, the moment still caught both actors off guard. When Ryder mentioned it during the press tour for Destination Wedding in 2018, Reeves turned to her and said, “Oh my gosh, we’re married.”
#4. She’s Naturally Blond
Winona Ryder’s hair has naturally darkened over time, but she revealed that it was “really blond” when she was younger. For her first film, Lucas, she dyed her hair black and was advised to keep it dark to match her quirky, unique image.
Still, Ryder has occasionally returned to her blond roots for certain roles. She played a blond as Babe in Mr. Deeds, and as Kim in Edward Scissorhands, where she embodied the classic blond cheerleader.
#5. She Took An Active Role In The Polly Klaas Case
In October 1993, 12-year-old Polly Klaas was abducted from a slumber party. Winona Ryder, who grew up near Polly’s hometown of Petaluma, CA, and shared her passion for acting, felt a deep connection to the young girl. Ryder offered a $200,000 reward in hopes of bringing Polly home safely. Sadly, Polly’s body was discovered a few months later.
Even after the case was resolved and Polly’s killer was imprisoned, Ryder remained committed to the cause, actively supporting the Polly Klaas Foundation, which helps find missing children. In honor of Polly, Ryder dedicated her 1994 film Little Women to her, knowing it was Polly’s favorite book.
#6. Veronica From ‘Heathers’ Is Her Favorite Role, Even Though She Was Warned Not To Take It
Veronica Sawyer, the witty and unexpectedly murderous lead in Heathers, is now one of Winona Ryder’s most iconic roles. But when Ryder first expressed interest in auditioning, her agent was convinced it would ruin her career. As Ryder recalled:
“My agent at the time literally got on her knees and begged me not to do [the movie]. She had her hands together, and she goes, ‘You will never. Work. Again.’”
Needless to say, the agent was wrong—and the two parted ways soon after. Today, Ryder is still a big Heathers fan, often quoting lines from the film, and like many fans, she’s eager for a sequel.
#7. She’s Had Late-Night Chats With Al Pacino
After her shoplifting incident, Winona Ryder reportedly began struggling with chronic insomnia. Fortunately, she didn’t go through those restless nights alone. She often found herself on late-night calls with her Simone co-star, Al Pacino. She shared with W magazine:
“We talk in the middle of the night. I don’t sleep; he doesn’t sleep. So it is very normal that we call each other at 2 in the morning. I just love him so much.”
Their friendship offered her a comforting connection during those sleepless times.
#8. She Grew Up On A Commune
Winona Ryder was born in a small farmhouse in Winona, MN—yes, she was named after her birthplace. After a brief move to San Francisco and some time in South America, her family eventually settled on a commune in Northern California, sharing “380 acres of redwoods” with six other families, as Ryder once described it.
While the commune had limited electricity, Ryder’s mother kept a tradition of showing movies on a projector, sparking Ryder’s early love for acting and film.
#9. Like Her Character In ‘Girl, Interrupted,’ She Stayed In A Psychological Ward
As Winona Ryder entered adulthood, the pressures of fame began to weigh heavily on her. At just 19, she struggled with depression, panic attacks, and anxiety. Feeling unable to confide in anyone, she ultimately checked into a mental health facility for help. Ryder described the hospital as a “very bare sort of stark place where they take everything away from you.”
Unfortunately, she found the experience unhelpful and didn’t discuss it for years. It wasn’t until she produced and starred in Girl, Interrupted, based on Susanna Kaysen’s memoir, that she finally opened up about her struggles.
#10. A Shoplifting Incident Almost Ended Her Career
In 2001, at the age of 31, Winona Ryder was arrested for stealing over $5,500 worth of merchandise from Saks Fifth Avenue in Beverly Hills, along with being found in possession of prescription painkillers. Though she was ultimately acquitted, the ordeal was incredibly distressing. During a court hearing, when her lawyer highlighted Ryder’s charitable work with the Polly Klaas Foundation, the deputy district attorney harshly responded, “What’s offensive to me is to trot out the body of a dead child.” This comment drew outrage from Polly’s father, who was present in court and later remarked that Ryder “may be a double felon, but she’s a double felon with a heart.”
Despite her acquittal, the fallout from the incident was significant. Ryder faced lost job opportunities and decided it was best to step back from acting to regroup. It wasn’t until 2010, with her role in Black Swan, that she began to reclaim her place in Hollywood.
#11. LSD Advocate Timothy Leary Was Her Godfather
Winona Ryder describes her parents—writer Cynthia Palmer and editor Michael Horowitz—as beatniks. Their circle included notable figures like poet Allen Ginsberg and Timothy Leary, a former Harvard professor famously labeled “the most dangerous man in America” by President Richard Nixon due to his advocacy for psychedelic substances. Leary, who was imprisoned approximately 36 times for his drug use and activism, was also Ryder’s godfather.
Growing up in this environment, Ryder adopted a straight-edge lifestyle, which she attributes to her parents’ efforts to demystify controlled substances.
Palmer and Horowitz are still married and remain engaged in discussions about the relationship between writers and drug use. They even compiled an anthology on the topic titled Sisters of the Extreme.
#12. She Has Two Bands Named After Her
Winona Ryder, a muse for various film directors, has also inspired musicians over the years. Notably, the Australian band the Veronicas took their name from her character in Heathers. Additionally, an indie-pop band from Montreal named Winona Forever drew inspiration from Johnny Depp’s tattoo, which he had inked in honor of his former fiancée. After their breakup, Depp altered the tattoo to read “Wino Forever.
Interestingly, Ryder’s own stage name was inspired by a musician, too. Her father was a huge fan of Mitch Ryder & the Detroit Wheels, and the musician’s name influenced Ryder’s choice.
