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Today, October 29th, 2021, Winona Ryder turns 50 years old. She was just 15 when she made her film debut in David Seltzer’s 1986 romantic dramedy film Lucas, and it didn’t take much longer until the actress became one of the most recognizable and distinctive screen stars of the ‘80s and ‘90s.
Ryder quickly became associated with off-kilter, eerie films, suiting her Halloween-season birthday. Early in her career, she established herself as a muse of sorts for Tim Burton, starring in his films Beetlejuice and Edward Scissorhands. She continued this trend by playing a murderous high schooler in the teen black comedy Heathers, and a psychiatric hospital patient in Girl, Interrupted.
Throughout the ‘90s, she became known as an indie darling — although to call her arresting stage presence as “darling” feels like a bit of an understatement. In the 2010s, she returned to the small screen as Joyce Byers in Netflix’s hit Stranger Things, solidifying her cross-generational appeal.
In celebration of her birthday, and the official arrival of Halloween Weekend, we’ve rounded up Winona Ryder’s top 10 performances, from the ‘80s to the 2020s. See where your favorite Ryder film ranked below.
— Abby Jones
10. Abigail Williams in The Crucible
Real witches aren’t scary, fake witches aren’t scary, nothing else is scary once you’ve looked into the crazed eyes of Abigial Williams. Ryder locates the frenzy behind the Salem Witch Trials, turning in the definitive performance of the greatest villain that Arthur Miller ever wrote. — Wren Graves
09. Evelyn Finkel in The Plot Against America
There’s nothing quite as infuriating as a contrarian who think they are independent, or a fascist who believes they’re fighting for freedom. Ryder’s Evelyn Finkel is a bad person, yes, but she’s convinced she’s working for good. The moment she finally understands the truth is as heartbreaking as it is satisfying. — W.G.
08. Lelaina Pierce in Reality Bites
While Ryder came of age under the bright lights of Hollywood in the early ’90s, her status as a Gen X icon was cemented with 1997’s Reality Bites. Though the Ben Stiller-directed dramedy only achieved minor success (and mixed reviews) after premiering at the Sundance Film Festival, it’s since become a cult classic in its consideration of the struggles of Ryder’s aspiring videographer Lelaina and the lives of her friends and roommates. — Glenn Rowley
07. Mina Murray in Dracula
In 1992, Ryder sank her teeth into the role of Mina Harker in Francis Ford Coppola’s big-screen adaptation of Bram Stoker’s Dracula. Also starring Gary Oldman as Count Dracula, Anthony Hopkins as Abraham Van Helsing, and Keanu Reeves as Jonathan Harker, the gothic drama’s pioneering impact on modern horror can’t be overstated. Not only is the film widely view the best vampire flick of all time, everything from Interview with a Vampire to the Twilight franchise owes a debt in one way or another to the way Dracula portrayed the blood-sucking undead on screen. Basically, would we even have Bella Swan without Winona? — G.R.
06. Jo March in Little Women
Long before Saoirse Ronan and Sutton Foster added their own spins to Jo March, Ryder inhabited the famous literary character in what many consider the gold standard of Little Women adaptations. Whether sparring with Christian Bale’s Laurie, doting on Claire Danes’ Beth, or being guided by Susan Sarandon’s Marmee, the actress injected Jo with just the right amount of warmth, ambition, loyalty, and heart. Critics and fans alike took notice of Ryder’s magnetic performance, which earned the then-23-year-old the second Academy Award nomination of her career. — G.R.
05. Susanna in Girl, Interrupted
Though she’d tackled many a dramatic role before, nothing in Ryder’s filmography was quite as serious as 1999’s Girl, Interrupted. Based on the memoir by Susanna Kaysen, the star played a fictionalized version of the author, who was checked into a psychiatric against her will following a suicide attempt in the 1960s. Through Ryder’s fellow patients — played by Angelina Jolie, Brittany Murphy, Elisabeth Moss, and more — the film touched on topics like self-harm, eating disorders, sexual abuse, and schizophrenia before Ryder faced off against Jolie’s sociopathic Lisa. Though Jolie would take home the Academy Award for Best Supporting Actress the following year, there’s no denying the psychological drama was anchored by Ryder’s stalwart performance. — G.R.
04. Joyce Byers in Stranger Things
In 2016, when Netflix revealed that their forthcoming original sci-fi thriller series would take place in 1980s suburbia, it felt like a no-brainer that Ryder would star. But rather than play the tortured teen, she took on the role as the mother of one: Her frenzied, distraught, and often delusional portrayal of Joyce Byers is convincing and heart-wrenching. — A.J.
03. Kim in Edward Scissorhands
As society barreled into the ’90s, Ryder continued her hot streak as a rising Hollywood It Girl as Kim Boggs in Edward Scissorhands. Reuniting with Tim Burton, the actress’ onscreen chemistry with Johnny Depp’s sweetly blade-handed humanoid bled into real life once filming wrapped. Though she was just 17 at the time (not to mention nine years his junior), Ryder and the future Jack Sparrow got engaged months before the fantasy romance premiered in theaters — though they’d break up three years later. Fast forward more than three decades and the actress would even reprise her role in a charming Super Bowl ad opposite Timothée Chalamet. — G.R.
02. Veronica in Heathers
What’s your damage, Heather?! Just twelve months after bursting onto the scene with Beetlejuice, Ryder took on the original trio of mean girls in 1989’s Heathers. In stark contrast to the feel-good teen movies being churned out by the likes of John Hughes at the time, the pitch-black satire presented suburban high school life as a social minefield filled foul-mouthed popular girls, murderous outcasts, and lots and lots of croquet. Though not technically a Heather by name, Ryder’s Veronica Sawyer inspired fear and a preppy fashion sense to kill for, all while gifting future generations with darkly snarky diary entries to look back on like, “Dear diary teen-angst bullshit now has a body count!” and “She’s my best friend. God, I hate her.” How very, indeed. — G.R.
01. Lydia in Beetlejuice
Beetlejuice, Beetlejuice, Beetlejuice! Could any other movie summon the top spot in Ryder’s career? We think not. As Lydia Deetz, the young actress delivered an unforgettable breakout performance, proving she could go toe-to-toe with everyone from Geena Davis and Alec Baldwin to Catherine O’Hara and the troublemaking poltergeist played by Michael Keaton himself. The film also kicked off a long and fruitful creative partnership with Tim Burton, and as fans of the spooky classic know, we haven’t been able to hear Harry Belafonte croon “Shake, shake, shake, señora!” the same way since. — G.R.