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1. Mermaids (1990)
directed by Richard Benjamin
featuring Cher, Bob Hoskins, Winona Ryder, Christina Ricci, Michael Schoeffling
There's no point in recounting the many production problems and personal hostilities which plagued the filming of Mermaids: the end result is all ... More
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2. Heathers (1989)
directed by Michael Lehmann
featuring Winona Ryder, Christian Slater, Shannen Doherty, Lisanne Falk, Kim Walker
A deliciously nasty black comedy, Heathers is set at a cliquish high school in Ohio. The most exclusive of those cliques is the Heathers, comprised ... More
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3. Alien Resurrection (1997)
directed by Jean-Pierre Jeunet
featuring Sigourney Weaver, Winona Ryder, Ron Perlman, Dominique Pinon, Michael Wincott
Two centuries after Ellen Ripley's death, doctors aboard the space station Auriga clone her using a blood sample taken from Fiorna 161, in hopes of ... More
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4. When Love Is Not Enough: The Lois Wilson Story (2010)
directed by John Kent Harrison
featuring Winona Ryder, Barry Pepper, John Bourgeois, Rosemary Dunsmore, Ellen Dubin
Winona Ryder stars as Lois Wilson, co-founder of Al-Anon and wife of Alcoholics Anonymous co-founder Bill Wilson (Barry Pepper), in this biopic ... More
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5. Sex and Death 101 (2008)
directed by Daniel Waters
featuring Simon Baker, Winona Ryder, Patton Oswalt, Leslie Bibb, Mindy Cohn
Upon receiving an e-mail containing the names of every woman he has ever slept with and every women he will ever sleep with, a man set to be married ... More
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6. Reality Bites (1994)
directed by Ben Stiller
featuring Winona Ryder, Ethan Hawke, Ben Stiller, Janeane Garofalo, Steve Zahn
This film was one of the more mainstream offerings in the array of films that emphasized the overly hyped "Generation X" phenomenon, a list that ... More
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7. The Last Word (2007)
directed by Geoff Haley
featuring Winona Ryder, Wes Bentley, Ray Romano, Gina Hecht
Wes Bentley and Winona Ryder star in director/screenwriter Geoff Haley's darkly comic romance centering on the relationship between a writer ... More
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8. Stay Cool (2011)
directed by Ted Smith
featuring Winona Ryder, Mark Polish, Sean Astin, Hilary Duff, Josh Holloway
A successful author is forced to contend with an unrequited crush from high school upon returning to his hometown to give the commencement speech to ... More
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9. Bram Stoker's Dracula (1992)
directed by Francis Ford Coppola
featuring Gary Oldman, Winona Ryder, Anthony Hopkins, Keanu Reeves, Richard E. Grant, Sadie Frost
Based on Bram Stoker's classic 1897 novel, this film from Francis Ford Coppola and screenwriter James Victor Hart offers a full-blooded portrait of ... More
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10. Edward Scissorhands (1990)
directed by Tim Burton
featuring Johnny Depp, Winona Ryder, Dianne Wiest, Anthony Michael Hall, Alan Arkin, Vincent Price, Kathy Baker
Tim Burton's Edward Scissorhands opens as an eccentric inventor (Vincent Price) lovingly assembles a synthetic youth named Edward (Johnny Depp). ... More
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11. Autumn in New York (2000)
directed by Joan Chen
featuring Richard Gere, Winona Ryder, Anthony LaPaglia, Elaine Stritch, Vera Farmiga
An man gets an unexpected lesson in love and life from a much younger woman in this romantic drama. Will Keane (Richard Gere) is a wealthy 50-year ... More
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12. The House of the Spirits (1993)
directed by Bille August
featuring Jeremy Irons, Meryl Streep, Glenn Close, Winona Ryder, Antonio Banderas
Bille August directed this film version of the Isabel Allende novel, featuring a cast that includes Jeremy Irons, Meryl Streep, and Glenn Close. The ... More
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13. The Age of Innocence (1993)
directed by Martin Scorsese
featuring Daniel Day-Lewis, Michelle Pfeiffer, Winona Ryder, Miriam Margolyes, Richard E. Grant, Alec McCowen
In Martin Scorsese's adaptation of Edith Wharton's 1920 novel, romance between an upper-class gentleman and an ostracized lady is doomed by 19th ... More
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14. Frankenweenie (2012)
directed by Tim Burton
featuring Charlie Tahan, Winona Ryder, Martin Landau, Catherine O'Hara
Tim Burton's 1984 short film Frankenweenie is resurrected for the big screen with this stop-motion 3D remake, which once again centers on a boy ... More
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15. How to Make an American Quilt (1995)
directed by Jocelyn Moorhouse
featuring Winona Ryder, Anne Bancroft, Maya Angelou, Ellen Burstyn, Kate Nelligan, Jean Simmons
A young woman at a crossroads in her life finds herself receiving plenty of advice from her older and wiser counterparts in this drama. Finn Dodd ... More
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16. The Crucible (1996)
directed by Nicholas Hytner
featuring Daniel Day-Lewis, Winona Ryder, Paul Scofield, Joan Allen, Bruce Davison
When Arthur Miller's play The Crucible was first staged in 1953, it was widely acclaimed as a metaphor for the recklessness of Joseph McCarthy and ... More
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17. The Dilemma (2011)
directed by Ron Howard
featuring Vince Vaughn, Kevin James, Jennifer Connelly, Winona Ryder, Channing Tatum, Queen Latifah
A lifelong bachelor struggles over whether to tell his best friend that his wife is cheating on him with another man in this comedy from director Ron ... More
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18. Little Women (1994)
directed by Gillian Armstrong
featuring Winona Ryder, Gabriel Byrne, Trini Alvarado, Samantha Mathis, Susan Sarandon, Kirsten Dunst, Claire Danes, Eric Stoltz, John Neville
Louisa May Alcott's classic novel about a family of women in Civil War-era New England is again brought to the screen in this adaptation. The focus ... More
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19. The Informers (2009)
directed by Gregor Jordan
featuring Billy Bob Thornton, Kim Basinger, Winona Ryder, Jon Foster, Amber Heard, Mickey Rourke
A collection of Bret Easton Ellis' short stories are adapted for the screen by Ellis and Nicholas Jarecki and helmed by Gregor Jordan in The ... More
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20. Lost Souls (2000)
directed by Janusz Kaminski
featuring Winona Ryder, Ben Chaplin, Sarah Wynter, Philip Baker Hall, John Hurt
A woman who has survived the touch of ultimate evil must now save one man from the same fate in order to protect the world in this supernatural ... More
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21. A Scanner Darkly (2006)
directed by Richard Linklater
featuring Keanu Reeves, Robert Downey, Jr., Woody Harrelson, Winona Ryder, Rory Cochrane
The war on drugs has been lost, and when a reluctant undercover cop is ordered to spy on those he is closest to, the toll that the mission takes on ... More
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22. The Private Lives of Pippa Lee (2009)
directed by Rebecca Miller
featuring Robin Wright, Blake Lively, Alan Arkin, Keanu Reeves, Maria Bello, Zoe Kazan, Winona Ryder
Rebecca Miller (The Ballad of Jack & Rose) adapts her own novel with this comedy drama about a woman who begins a second life after her husband ... More
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23. The Darwin Awards (2007)
directed by Finn Taylor
featuring Joseph Fiennes, Winona Ryder, Tim Blake Nelson, Wilmer Valderrama, David Arquette
When a San Francisco homicide detective with a keen eye for criminal profiling is fired for botching the arrest of a notorious serial killer, his ... More
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24. Black Swan (2010)
directed by Darren Aronofsky
featuring Natalie Portman, Mila Kunis, Vincent Cassel, Barbara Hershey, Winona Ryder, Benjamin Millepied
New York City ballet dancer Nina (Natalie Portman) enters into an intense battle of wills with a talented and ambitious new arrival (Mila Kunis) who ... More
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25. Welcome Home, Roxy Carmichael (1990)
directed by Jim Abrahams
featuring Winona Ryder, Jeff Daniels, Laila Robins, Thomas Wilson Brown, Joan McMurtrey
In this film, the small town of Clyde, Ohio is buzzing with excitement when it is said that the famous Roxy Carmichael is leaving her luxurious ... More
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