Winona Ryder has most recently found success as Joyce Byers in the hugely popular Netflix series Stranger Things, but she's undoubtedly most famous for her movie roles.
Ryder rose to prominence in the mid-late 1980s, with her first film role coming in 1986's Lucas. Since then, she's appeared in some genuinely iconic movies, and we're going to rank her 22 best, all the way up to her finest film.
She has a credit in, Being John Malkovich, which would arguably be the best movie on this list, but it was merely archive footage. Therefore we won't be including it here.
1. How to Make an American Quilt (1995, directed by Jocelyn Moorhouse)
How to Make an American Quilt is a drama movie based on Whitney Otto's 1991 novel. It's about a bride-to-be listening to stories of romance and sorrow told by her elders as they construct a quilt meant as a wedding gift for when she gets married.
Ryder somewhat awkwardly plays the main character Finn Dodd, engaged to Dermot Mulroney's Sam. The rest of the cast includes Anne Bancroft, Ellen Burstyn, and Alfre Woodward, who're charming. How to Make an American Quilt is like a casual chat between real women, making it incredibly endearing. It's funny, soulful, and a little quirky.
2. Great Balls of Fire! (1989, directed by Jim McBride)
Great Balls of Fire! is a biographical drama movie about rockabilly pioneer Jerry Lee Lewis based on Myra Lewis and Murray M. Silver Jr.'s 1982 biography. It depicts his wildly controversial life, which included alcoholism and marrying an underage girl.
Giving a brilliant and mature performance, Ryder portrays Myra Gale Brown, the 13-year-old girl Lewis fell in love with and eloped with. Great Balls of Fire! romanticizes some of Lewis' more-than-questionable behavior, but it's still a terrific film. Dennis Quaid is lively in the leading role, features lots of iconic music, and is fun and energetic.
3. Zoolander (2001, directed by Ben Stiller)
Zoolander is a comedy movie based loosely on two short films directed by Russell Bates and written by Drake Sather and Stiller for the 1996 and 1997 VH1 Fashion Awards television specials. It's about the life of a dimwitted supermodel, the eponymous Derek Zoolander.
It's an intentionally stupid film with clever undertones, but you must understand it's deliberately stupid to enjoy it. If you do that, you'll find Zoolander to be genuinely funny. Stiller is a joy in the eponymous role, and the eclectic supporting ensemble includes Owen Wilson, Will Ferrell, Milla Jovovich, David Duchovny, Jon Voight, and Vince Vaughn. Ryder has a mere cameo as herself, flirting with Zoolander, and embraces her silly role.
4. Reality Bites (1994, directed by Ben Stiller)
Reality Bites is a romantic comedy-drama about an aspiring filmmaker working on the eponymous Reality Bites documentary about the unsatisfied lives her friends and roommates are living.
Ryder plays Lelaina Pierce, the aspiring filmmaker mentioned above, with humor and authenticity. Her chemistry with Ethan Hawke, who plays her love interest, Troy Dyer, is perfect. Reality Bites is a movie that almost everyone will find relatable moments in. It's engaging, funny, and an impressive directorial debut for Stiller, who also appears in the film.
5. The Iceman (2012, directed by Ariel Vromen)
The Iceman is a biographical crime movie loosely based on the life of notorious criminal and convicted murderer Richard Kuklinski. The film depicts his life of crime and arrest, which reveals his illegal activities to his wife and family for the first time.
Ryder plays Deborah Kuklinski, the character based on Richard's wife, Barbara. She's terrific and holds her own in a brilliant male-dominated cast that includes Michael Shannon as Richard, Ray Liotta, Chris Evans, James Franco, David Schwimmer, Stephen Dorff, and Robert Davi. The Iceman is well-acted, slick, and riveting.
6. A Scanner Darkly (2006, directed by Richard Linklater)
A Scanner Darkly is an adult animated psychological sci-fi thriller set in a not-too-distant future about an undercover police officer who gets involved with a dangerous new drug and begins to lose his identity because of it.
Keanu Reeves plays the undercover cop in a typically relaxed style, and Ryder expertly plays a character called Donna Hawthorne, AKA Audrey, AKA “Hank” (it's complicated). Other prominent cast members include Robert Downey Jr. and Woody Harrelson. A Scanner Darkly is a visually stunning, almost hypnotic, creepy, and engaging film that vividly depicts a drug-ridden and politically unstable world.
7. The Crucible (1996, directed by Nicholas Hytner)
The Crucible is a historical drama movie based on Arthur Miller's 1953 play. It's about a Salem, Massachusetts, resident and her attempts to frame her ex-lover's wife for being a witch during the infamous 1692 witchcraft trials.
Ryder plays Abigail Williams, a child forced to lie to help frame the woman as a witch. She's outstanding, as is the ever-dependable Daniel Day-Lewis in the lead role of John Proctor. The Crucible received two Academy Award nominations for Best Adapted Screenplay and Best Supporting Actress for Joan Allen. It's a brilliant adaptation of the play that's powerful, well-acted, and boasts excellent production design.
8. The Private Lives of Pippa Lee (2009, directed by Rebecca Miller)
The Private Lives of Pippa Lee is a romantic comedy-drama based on director Miller's 2008 novel. It's about the eponymous Pippa Lee, whose marriage to a much older man results in her getting forced to move to a retirement community, where she reflects on her life and has a nervous breakdown.
Robin Wright is excellent in the lead role of Pippa, and Blake Lively is great as the younger version of the character. The supporting cast includes Keanu Reeves, Alan Arkin, Maria Bello, and Monica Bellucci. Ryder plays Sandra Dulles, a neighbor of Pippa's who wants to leave her husband, and she's excellent. The Private Lives of Pippa Lee is undoubtedly offbeat but well-performed, intelligently satirical, and darkly funny.
9. Mermaids (1990, directed by Richard Benjamin)
Mermaids is a family comedy-drama movie based on Patty Dann's 1986 novel. It's about an anxiety-ridded teenage girl who moves with her headstrong mother and young sister to a small town in Massachusetts, having moved several times previously whenever her mother's relationships ended.
Ryder plays Charlotte Flax, the neurotic teen mentioned above, and she's the film's highlight. Cher plays her mother, Christina Ricci plays her younger sister, and Bob Hoskins plays her mother's love interest in an exceptional cast. Mermaids is a heartfelt, gentle, witty, funny, and brilliant coming-of-age story that anyone can enjoy.
10. Lucas (1986, directed by David Seltzer)
Lucas is a romantic comedy-drama movie about a socially awkward fourteen-year-old whose first experience of heartbreak occurs when his two closest friends – an older-brother figure and the new girl in town who he's fallen for – fall for each other.
Ryder's acting debut was in this film, and she's terrific as the eponymous Lucas Blye's friend Rina. Corey Haim plays Lucas, and Martin Sheen and Kerri Green play his two friends who fall for each other. It's a fantastic young cast that provides the movie with good energy. Lucas is sweet, poignant, well-acted, and has a lovely positive message about friendship.
11. Night on Earth (1991, directed by Jim Jarmusch)
Night on Earth is a comedy-drama art movie in the form of a collection of five vignettes. All five stories occur on the same night and focus on the bonds formed between taxi drivers and passengers in five cities worldwide: Los Angeles, New York, Paris, Rome, and Helsinki.
Ryder plays Corky, a no-nonsense Los Angeles cab driver whose customer is a Hollywood casting agent, and she's excellent. Night on Earth is such an underrated gem. It's undoubtedly a weird film that lacks big moments, but it's incredibly engaging, funny, relatable, and a thoughtful examination of humans.
12. Bram Stoker's Dracula (1992, directed by Francis Ford Coppola)
Bram Stoker's Dracula is a Gothic horror movie based on Stoke's 1897 novel, Dracula. It follows the centuries-old vampire Count Dracula to England, where he plans to seduce his barrister's fiancée, believing her to be his wife reincarnate, and wreak havoc all over the foreign land.
This movie was the first in a long time to portray Dracula, played by Gary Oldman here, as genuinely terrifying and not a campy shadow of the original creation. Bram Stoker's Dracula is teeming with outstanding performances (Keanu Reeves aside, sadly), including Ryder as Mina Harker, the woman Dracula wants to seduce. It's eerie and romantic and deservedly won three of the four Academy Awards it received nominations for; Best Costume Design, Best Sound Editing, and Best Makeup.
13. Looking for Richard (1996, directed by Al Pacino)
Looking for Richard is a hybrid movie that includes a filmed performance of selected scenes from William Shakespeare's Richard III and a documentary exploring the continuing role and relevance in popular culture of the iconic English playwright and his works.
It's Pacino's directorial debut, and it's brilliant. He plays himself and Richard III in the documentary and film, respectively. Ryder gives a competent performance in the movie as Lady Anne Neville. Other performers and commenters in the star-studded cast include Vanessa Redgrave, Kenneth Branagh, James Earl Jones, Kevin Spacey, Kevin Kline, and Alec Baldwin. Looking for Richard is a genuinely mesmerizing, informative, and energetic behind-the-scenes look at adapting Shakespeare.
14. Experimenter (2015, directed by Michael Almereyda)
Experimenter is a biographical drama movie based on and depicting the 1961 Milgram experiments conducted by Yale University psychologist Stanley Milgram, which tested ordinary human's obedience to authority figures.
Peter Sarsgaard performs compellingly as Milgram, and Ryder superbly plays his wife Alexandra, AKA “Sasha.” Experimenter raises many intriguing questions and provokes a lot of thought about human behavior. It's engaging, profound, stylish, playful, and weird but entertaining.
15. Frankenweenie (2012, directed by Tim Burton)
Frankenweenie is a 3D stop-motion animated sci-fi horror comedy movie. It's a feature-length remake of director Burton's 1984 short film based on Mary Shelley's 1818 book Frankenstein; or, The Modern Prometheus. It's about a young boy who uses electricity to resurrect his dead Bull Terrier, resulting in his peers discovering what he's done and reanimating their deceased pets and other creatures, causing utter havoc.
Ryder voices Elsa Van Helsing, a kind classmate of Victor Frankenstein, the boy who brings his dog back to life. She's fabulous in the role as part of a terrific cast that includes Catherine O'Hara, Martin Short, and Martin Landau. Frankenweenie is an aesthetically beautiful, energetic, eccentric, and somewhat peculiar movie that children, in particular, will love.
16. The Age of Innocence (1993, directed by Martin Scorsese)
The Age of Innocence is a historical romantic drama based on Edith Wharton's 1920 novel. Set in nineteenth-century New York high society, it's about a young lawyer who falls for a woman separated from her husband while he's engaged to said woman's cousin.
Ryder charmingly plays May Welland, the respectable woman whose cousin her husband-to-be falls in love with. She holds her own in a formidable cast that includes Daniel Day-Lewis, Michelle Pfeiffer, Miriam Margolyes, Michael Gough, and Richard E. Grant. The Age of Innocence is a bloody, brutal, romantic, exemplary film amazingly performed by its impressive ensemble.
17. Little Women (1994, directed by Gillian Armstrong)
Little Women is a coming-of-age historical drama based on Louisa May Alcott's 1868-69 two-volume novel. It follows the exploits of the four March sisters as they live and grow up in post-Civil War America.
Kirsten Dunst and Samantha Mathis (playing one sister at different ages), Clare Danes, Trini Alvarado, and Ryder play the four sisters. Ryder is superb as Josephine “Jo” March and earned a nomination for the Academy Award for Best Actress. Little Women earned three nominations in total, sadly winning none. It's a timeless story that's intelligent, warm, and wonderfully performed by its predominantly female cast (although the likes of Gabriel Byrne, Christian Bale, and Eric Stoltz have prominent roles too).
18. Star Trek (2009, directed by J.J. Abrams)
Star Trek is a sci-fi action movie, the eleventh overall movie in the eponymous franchise, and the first in a reboot series that has spawned three movies so far (there's another on the way). This one sees James T. Kirk doing his best to live up to his father's legacy as a vengeful Romulan from the future looks to destroy the Federation planet by planet.
Ryder plays the iconic role of Spock's human mother, Amanda Grayson, and she does a grand job. Star Trek's phenomenal cast includes Chris Pine, Zachary Quinto, Leonard Nimoy, Zoe Saldana, Karl Urban, Simon Pegg, Anton Yelchin, and Eric Bana. It's action-packed, visually spectacular, funny, and perfectly suitable for fans of the classic series and newcomers to the franchise.
19. Beetlejuice (1988, directed by Tim Burton)
Beetlejuice is a fantasy comedy horror movie about a recently deceased couple who, as ghosts residing in their former home, contact the eponymous deviant “bio-exorcist” to scare away the house's obnoxious new inhabitants.
A truly unique and bizarre movie, Beetlejuice is also joyfully brilliant. It boasts incredible aesthetics and fantastic creativity and can creep you out and make you howl with laughter. Ryder plays Lydia Deetz, the daughter of the family that the eponymous character attempts to frighten, and she's iconic in the role. The excellent cast includes Michael Keaton as Beetlejuice, Alec Baldwin, Geena Davis, Jeffrey Jones, and Catherine O'Hara. Beetlejuice won the Academy Award for Best Makeup.
20. Black Swan (2010, directed by Darren Aronofsky)
Black Swan is a psychological horror about a talented but mentally unstable ballerina on the verge of stardom who loses grip on reality and falls into a waking nightmare when her work pushes her to the breaking point.
Ryder plays retired prima ballerina Elizabeth “Beth” MacIntyre and is outstanding along with the rest of the cast, which includes Natalie Portman, Mila Kunis, Vincent Cassel, and Barbara Hershey. Black Swan received nominations for five Academy Awards, including Best Picture and Best Director, winning one for Best Actress for Portman. It's creative, passionate, intense, and a little creepy.
21. Edward Scissorhands (1990, directed by Tim Burton)
Edward Scissorhands is a fantasy romance movie about an unfinished artificial humanoid, built by a now-deceased inventor, who has scissors where his hands and fingers should be, and gets taken in by a suburban family and then falls in love with their teenage daughter.
Ryder plays Kim Boggs, the young girl with whom the eponymous character falls in love. She's brilliant, as is Johnny Depp as Edward. The excellent supporting cast includes Anthony Michael Hall, Dianne Wiest, Kathy Baker, Alan Arkin, Conchata Ferrell, and Vincent Price as the inventor. Edward Scissorhands is sweet, strange, funny, and delightfully entertaining from beginning to end.
22. Heathers (1989, directed by Michael Lehmann)
Heathers is a teen black comedy movie that follows four teenage girls, three of whom are named Heather, in a clique at an Ohio high school. One of their lives gets interrupted when a misanthrope arrives, intent on murdering the popular kids and staging their deaths as suicides.
Veronica Sawyer, the only one of the four main characters not named Heather, is played brilliantly by Ryder. Heathers is a great and vastly underrated movie, and it's subversive and a little nasty but incredibly watchable, excellently acted, and able to provoke shock and profound thought.
Writer and editor with ten years of experience working full-time in this capacity. I've written over 2000 pieces of published work and managed teams of 50+ writers. I've produced content for some of the world's most prominent entertainment and sports platforms. My published work includes feature articles, news and opinion pieces, listicles, quizzes, voice-over scripts, viral content, and more. I'm a British 80s kid who loves movies (horror, superhero stuff, and all things 80s are my favorites), boxing, and football (soccer), a former business owner and executive headhunter, and a Tottenham Hotspur FC fan for my sins.