Winona Ryder films: Best to Worst (all her films)
by Gwasgray | created - 06 Jan 2013 | updated - 6 months ago | PublicAs you can probably tell, I have a bit of a thing for Winona.
The top 10 may be different to my other list "The Best of Winona Ryder" but that list is meant to be the films that give the best an all-round view of Winona's career (so for example Star Trek was left out because her part is pretty small). This list judges her films by themselves.
I've seen Turks & Caicos but I've chosen to leave that out because I consider it to be a TV drama program rather than a movie (or TV movie) Looking for Richard doesn't count because it's a documentary (ditto other documentaries she's appeared in) and Being John Malkovich just uses a bit of archive footage of her (at an awards show).
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1. Black Swan (2010)
R | 108 min | Drama, Thriller
Nina is a talented but unstable ballerina on the verge of stardom. Pushed to the breaking point by her artistic director and a seductive rival, Nina's grip on reality slips, plunging her into a waking nightmare.
Director: Darren Aronofsky | Stars: Natalie Portman, Mila Kunis, Vincent Cassel, Winona Ryder
Votes: 823,745 | Gross: $106.95M
I think this an amazing film, a thrilling journey into madness. And it's perfect that Winona was cast as the veteran performer who up-and-coming Natalie Portman takes the place of. You have to admit there's a real-life parallel there.
2. Edward Scissorhands (1990)
PG-13 | 105 min | Drama, Fantasy, Romance
The solitary life of an artificial man - who was incompletely constructed and has scissors for hands - is upended when he is taken in by a suburban family.
Director: Tim Burton | Stars: Johnny Depp, Winona Ryder, Dianne Wiest, Anthony Michael Hall
Votes: 523,414 | Gross: $56.36M
The beginning of Tim Burton and Johnny Depp's longtime collaboration and one of their best.
3. Beetlejuice (1988)
PG | 92 min | Comedy, Fantasy
The spirits of a deceased couple are harassed by an unbearable family that has moved into their home, and hire a malicious spirit to drive them out.
Director: Tim Burton | Stars: Alec Baldwin, Geena Davis, Michael Keaton, Annie McEnroe
Votes: 339,583 | Gross: $73.71M
The first proper Tim Burton film (with Pee-Wee's Big Adventure he was more of a hired gun), with bags of originality and charm and the Tim Burton-isms feel completely fresh - the expressionist set designs, the costumes, the Danny Elfman score and stop-motion sequences. Lydia Deetz is the most Tim Burton-esque characters ever and one of Winona's most iconic roles.
4. The Crucible (1996)
PG-13 | 124 min | Drama, History
A Salem resident attempts to frame her ex-lover's wife for being a witch in the middle of the 1692 witchcraft trials.
Director: Nicholas Hytner | Stars: Daniel Day-Lewis, Winona Ryder, Paul Scofield, Joan Allen
Votes: 40,147 | Gross: $7.34M
5. Mermaids (1990)
PG-13 | 110 min | Comedy, Drama, Romance
An unconventional single mother relocates with her two daughters to a small Massachusetts town in 1963, where a number of events and relationships both challenge and strengthen their familial bonds.
Director: Richard Benjamin | Stars: Cher, Bob Hoskins, Winona Ryder, Michael Schoeffling
Votes: 35,817 | Gross: $35.42M
Sweet, quirky, slightly corny but lovable little film. Winona is so convincing and endearing as a naive, confused, virginal 15 year old (she was about 18 at the time) I think it's one of her best performances.
6. Heathers (1988)
R | 103 min | Comedy, Crime
At Westerburg High where cliques rule, jocks dominate and all the popular girls are named Heather, it's going to take a Veronica and mysterious new kid to give teen angst a body count.
Director: Michael Lehmann | Stars: Winona Ryder, Christian Slater, Shannen Doherty, Lisanne Falk
Votes: 115,693 | Gross: $1.11M
Personally I feel it's slightly overrated and you can tell it didn't completely live up to scriptwriter Daniel Waters' dream (he originally wanted it Stanley Kubrick to direct it) but Christian Slater steals the show with his Nicholson-esque coolness. One of Winona's best performances as well.
7. Girl, Interrupted (1999)
R | 127 min | Biography, Drama
A directionless teenager, Susanna, is rushed to Claymoore, a mental institution, after a supposed suicide attempt. There, she befriends a group of troubled women who deeply influence her life.
Director: James Mangold | Stars: Winona Ryder, Angelina Jolie, Clea DuVall, Brittany Murphy
Votes: 211,028 | Gross: $28.87M
Flawed but occaissionally effective adaptation of a good but very difficult to adapt book. Most notable for being the film that won very soon-to-be Hollywood's hottest actress Angelina Jolie her Oscar.
8. Little Women (1994)
PG | 115 min | Drama, Family, Romance
The March sisters live and grow in post-Civil War America.
Director: Gillian Armstrong | Stars: Susan Sarandon, Winona Ryder, Kirsten Dunst, Claire Danes
Votes: 63,531 | Gross: $50.08M
Winona does a good job (she even earned a Best Actress Oscar nom) in this solid adaptation of a classic children's story.
9. The Age of Innocence (1993)
PG | 139 min | Drama, Romance
A tale of nineteenth-century New York high society in which a young lawyer falls in love with a woman separated from her husband, while he is engaged to the woman's cousin.
Director: Martin Scorsese | Stars: Daniel Day-Lewis, Michelle Pfeiffer, Winona Ryder, Linda Faye Farkas
Votes: 67,707 | Gross: $32.20M
10. Star Trek (2009)
PG-13 | 127 min | Action, Adventure, Sci-Fi
The brash James T. Kirk tries to live up to his father's legacy with Mr. Spock keeping him in check as a vengeful Romulan from the future creates black holes to destroy the Federation one planet at a time.
Director: J.J. Abrams | Stars: Chris Pine, Zachary Quinto, Simon Pegg, Leonard Nimoy
Votes: 620,006 | Gross: $257.73M
Successful reboot of the Star Trek movie franchise. Only a small cameo role for Winona though (playing Spock's mother)
11. Frankenweenie (2012)
PG | 87 min | Animation, Comedy, Drama
When a boy's beloved dog passes away suddenly, he attempts to bring the animal back to life through a powerful science experiment.
Director: Tim Burton | Stars: Winona Ryder, Catherine O'Hara, Martin Short, Martin Landau
Votes: 117,023 | Gross: $35.29M
Admittedly it does feel like Tim Burton is repeating himself again, but I still liked this. It had a nicely dark sense of humour and great performances from it's voice cast. Winona however gets disappointingly few lines as schoolgirl Elsa Van Helsing (a bit like a hybrid of Lydia Deetz and Rina from Lucas)
12. Night on Earth (1991)
R | 129 min | Comedy, Drama
An anthology of 5 different cab drivers in 5 American and European cities and their remarkable fares on the same eventful night.
Director: Jim Jarmusch | Stars: Winona Ryder, Gena Rowlands, Lisanne Falk, Alan Randolph Scott
Votes: 65,931 | Gross: $2.02M
Typically quirky and eclectic collection of stories from Jim Jarmusch. Winona is cast against type as a tomboy cabbie/grease monkey.
13. Bram Stoker's Dracula (1992)
R | 128 min | Drama, Fantasy, Horror
The centuries old vampire Count Dracula comes to England to seduce his barrister Jonathan Harker's fiancée Mina Murray and inflict havoc in the foreign land.
Director: Francis Ford Coppola | Stars: Gary Oldman, Winona Ryder, Anthony Hopkins, Keanu Reeves
Votes: 238,178 | Gross: $82.52M
14. The House of the Spirits (1993)
R | 145 min | Drama, Romance
A rancher, his clairvoyant wife, and their family face turbulent years in South America in this adaptation of Isabel Allende's best-seller.
Director: Bille August | Stars: Jeremy Irons, Meryl Streep, Maria Conchita Alonso, António Assunção
Votes: 24,931 | Gross: $6.27M
15. Alien: Resurrection (1997)
R | 109 min | Action, Horror, Sci-Fi
Two centuries after her death, a powerful human/alien hybrid clone of Ellen Ripley aids a crew of space pirates in stopping the aliens from reaching Earth.
Director: Jean-Pierre Jeunet | Stars: Sigourney Weaver, Winona Ryder, Dominique Pinon, Ron Perlman
Votes: 263,177 | Gross: $47.75M
16. Experimenter (2015)
PG-13 | 98 min | Biography, Drama, History
In 1961, famed social psychologist Stanley Milgram conducted a series of radical behavior experiments that tested ordinary humans' willingness to obey authority.
Director: Michael Almereyda | Stars: Peter Sarsgaard, Winona Ryder, Jim Gaffigan, Anthony Edwards
Votes: 19,666 | Gross: $0.16M
17. A Scanner Darkly (2006)
R | 100 min | Animation, Comedy, Crime
An undercover cop in a not-too-distant future becomes involved with a dangerous new drug and begins to lose his own identity as a result.
Director: Richard Linklater | Stars: Keanu Reeves, Winona Ryder, Robert Downey Jr., Rory Cochrane
Votes: 117,064 | Gross: $5.50M
The rotoscoping is bold but sags somewhat because much of the running time is taken up by the drug-addled characters sitting around talking nonsense (might sound funny but it's not really) with an irritating Robert Downey Jr. producing the most verbal diarrhoea.
18. Reality Bites (1994)
PG-13 | 99 min | Comedy, Drama, Romance
A documentary filmmaker and her fellow Generation X graduates face life after college, looking for work and love in Houston.
Director: Ben Stiller | Stars: Winona Ryder, Ethan Hawke, Janeane Garofalo, Steve Zahn
Votes: 53,586 | Gross: $20.98M
19. Lucas (1986)
PG-13 | 100 min | Comedy, Drama, Romance
A socially inept fourteen-year-old experiences heartbreak for the first time when his two best friends - Cappie, an older-brother figure, and Maggie, the new girl with whom he is in love - fall for each other.
Director: David Seltzer | Stars: Corey Haim, Kerri Green, Charlie Sheen, Courtney Thorne-Smith
Votes: 17,518 | Gross: $8.20M
Sweet but quite dated 80s high school movie with a performance from tragic child star Corey Haim that shows what could have been. A very young and untested Winona debuts as a shy classmate with a unrequited crush on the title character.
20. Great Balls of Fire! (1989)
PG-13 | 108 min | Biography, Drama, Music
The life and career of wildly controversial rock 'n' roll star Jerry Lee Lewis.
Director: Jim McBride | Stars: Dennis Quaid, Winona Ryder, John Doe, Stephen Tobolowsky
Votes: 18,874 | Gross: $13.74M
Silly but entertaining, and the music's still great. Then-18-year-old Winona makes a fairly convincing 13-year-old (as Lewis' underaged bride)
21. Zoolander (2001)
PG-13 | 90 min | Comedy
At the end of his career, a clueless fashion model is brainwashed to kill the Prime Minister of Malaysia.
Director: Ben Stiller | Stars: Ben Stiller, Owen Wilson, Christine Taylor, Will Ferrell
Votes: 291,603 | Gross: $45.17M
Winona has a short cameo playing herself in this funny Ben Stiller comedy which now has a bit of a cult following.
22. Celebrity (1998)
R | 113 min | Comedy, Drama
The fortunes of a husband and wife differ drastically after they divorce.
Director: Woody Allen | Stars: Kenneth Branagh, Judy Davis, Leonardo DiCaprio, Greg Mottola
Votes: 28,400 | Gross: $5.03M
Average Woody Allen film with Kenneth Branagh playing Woody Allen. Winona gets 4 scenes but is certainly believable as someone he'd fall in love with at first sight.
23. The Private Lives of Pippa Lee (2009)
R | 98 min | Comedy, Drama, Romance
After her much older husband forces a move to a suburban retirement community, Pippa Lee engages in a period of reflection and finds herself heading toward a quiet nervous breakdown.
Director: Rebecca Miller | Stars: Robin Wright, Alan Arkin, Mike Binder, Winona Ryder
Votes: 14,218
Another recent minor supporting role for Winona but I think she made the most of it.
24. Homefront (I) (2013)
R | 100 min | Action, Crime, Thriller
A former DEA agent moves his family to a quiet town, where he soon tangles with a local meth druglord.
Director: Gary Fleder | Stars: Jason Statham, James Franco, Winona Ryder, Kate Bosworth
Votes: 130,077 | Gross: $20.16M
Wasn't expecting much but actually it wasn't that bad. Winona, playing a ex-biker gang groupie, doesn't get that much to do apart from acting as a go-between for James Franco's meth dealer and a biker gang but it's a new kind of character for her and she just about pulls it off.
25. The Iceman (2012)
R | 106 min | Biography, Crime, Drama
The story of Richard Kuklinski, the notorious contract killer and family man. When he was finally arrested in 1986, neither his wife nor his daughters had any clue about his real profession.
Director: Ariel Vromen | Stars: Michael Shannon, Chris Evans, James Franco, Winona Ryder
Votes: 79,324 | Gross: $1.94M
Has a good cast but it's a bit flat and doesn't seem to really bring anything new to the gangster genre. Winona is second billed and gets the second most screentime but her scenes are quite brief and she still feels underused.
26. Destination Wedding (2018)
R | 87 min | Comedy, Drama, Romance
The story of two miserable and unpleasant wedding guests, Lindsay and Frank, who develop a mutual affection despite themselves.
Director: Victor Levin | Stars: Winona Ryder, Keanu Reeves, DJ Dallenbach, Ted Dubost
Votes: 33,356
A two-hander, basically a relentless stream of acerbic cracks. Hit and miss really but there are some quite good lines. Keanu is too wooden to really get the most out of it, Winona gives the better performance.
27. Square Dance (1987)
PG-13 | 112 min | Drama, Romance
A 13-year-old girl changes a pleasant life in the countryside for a troubled life in the city.
Director: Daniel Petrie | Stars: Jason Robards, Jane Alexander, Winona Ryder, Rob Lowe
Votes: 1,072 | Gross: $0.23M
Low budget 80s TV movie that isn't too bad for what it is. Winona's second film and her first leading role (although as a starting-out child actress she only gets 3rd billing)
28. When Love Is Not Enough: The Lois Wilson Story (2010 TV Movie)
PG | 92 min | Biography, Drama
Based on the true story of the enduring but troubled love between Lois Wilson, co-founder of Al-Anon, and her alcoholic husband Bill Wilson, co-founder of Alcoholics Anonymous.
Director: John Kent Harrison | Stars: Winona Ryder, Barry Pepper, John Bourgeois, Rosemary Dunsmore
Votes: 1,219
Fairly cheesy Hallmark TV movie although has a few good scenes where Winona and Barry Pepper pull some decent performances out of the bag.
29. S1m0ne (2002)
PG-13 | 117 min | Comedy, Drama, Sci-Fi
A producer's film is endangered when his star walks off, so he decides to digitally create an actress to substitute for the star, becoming an overnight sensation that everyone thinks is a real person.
Director: Andrew Niccol | Stars: Al Pacino, Catherine Keener, Rachel Roberts, Benjamin Salisbury
Votes: 62,434 | Gross: $9.68M
Corny comedy sci-fi fantasy, Al Pacino's worst film after Gigli and Jack & Jill. Winona gets about 5 minutes of screentime playing "a supermodel with a SAG card" (but isn't she a bit short to be a model?)
30. Autumn in New York (2000)
PG-13 | 103 min | Drama, Romance
Romantic drama about an aging playboy who falls for a sweet, but terminally ill, young woman.
Director: Joan Chen | Stars: Richard Gere, Winona Ryder, Anthony LaPaglia, Elaine Stritch
Votes: 28,270 | Gross: $37.75M
Unfortunately mawkish weepy with an ending that anyone could see from miles away. Richard Gere gives a typical Richard Gere performance (ie. pretty wooden) but at least Winona is very gorgeous most of the time.
31. Welcome Home, Roxy Carmichael (1990)
PG-13 | 95 min | Comedy, Drama
A small town prepares for the homecoming of superstar Roxy Carmichael, as does a young outsider, who believes Roxy is her mother.
Director: Jim Abrahams | Stars: Winona Ryder, Jeff Daniels, Laila Robins, Thomas Wilson Brown
Votes: 5,924 | Gross: $3.99M
32. How to Make an American Quilt (1995)
PG-13 | 117 min | Comedy, Drama, Romance
Bride-to-be Finn Dodd hears tales of romance and sorrow from her elders as they construct a quilt.
Director: Jocelyn Moorhouse | Stars: Winona Ryder, Ellen Burstyn, Anne Bancroft, Kaelynn Craddick
Votes: 12,499 | Gross: $23.57M
All the older women's stories are too thinly sketched, it has some pretty corny moments and in the end it feels like something churned out to attract middle-aged, middle American women. Ellen Burstyn, Anne Bancroft, Maya Angelou and prestigious name must have been the reason Winona signed onto this, it surely couldn't have been because of the quality of the script or the wishy-washy character she plays.
33. Sex and Death 101 (2007)
R | 117 min | Comedy, Drama, Fantasy
A guy's life is turned around by an e-mail that includes the names of everyone he's had sex with--and ever will have sex with. His situation gets worse when he encounters a femme fatale (Ryder) who targets men guilty of sex crime.
Director: Daniel Waters | Stars: Robert Wisdom, Tanc Sade, Patton Oswalt, Simon Baker
Votes: 11,583 | Gross: $0.02M
Winona reunites with Heathers writer Daniel Waters but the results are a bit disappointing (this certainly won't develop the cult following of Heathers)
34. Stay Cool (2009)
PG-13 | 94 min | Comedy, Drama, Romance
An author who returns to his hometown to deliver a commencement address to a class of graduating high school students has to deal with his feelings for an old flame as well as the advances of a student who has the hots for him.
Director: Michael Polish | Stars: Winona Ryder, Mark Polish, Sean Astin, Hilary Duff
Votes: 3,614
35. The Heart Is Deceitful Above All Things (2004)
R | 97 min | Drama
Seven-year-old Jeremiah is pulled from his foster home and thrown into a troubled life on the road with his teenage mother, Sarah.
Director: Asia Argento | Stars: Asia Argento, Dylan Sprouse, Cole Sprouse, Jimmy Bennett
Votes: 7,134 | Gross: $0.03M
A depressing film that feels like it's just being gritty for the sake of it and has little else to say. And the "true story" it's based on turned out to be a hoax. Winona appears in one 2 minute scene playing a caricatured child psychologist, with a bad southern accent (accents aren't really her strong suit)
36. The Letter (IV) (2012)
R | 92 min | Drama, Mystery, Thriller
A playwright who begins to mentally unravel cannot decide if she is at the center of a manipulative plot or simply losing her grip on reality.
Director: Jay Anania | Stars: Winona Ryder, Josh Hamilton, Marin Ireland, Katherine Waterston
Votes: 1,704
Had some potential, the performances aren't bad and it's nice to see Winona in a starring role again (she gets more of a chance to act), it's just a shame the story doesn't go anywhere. It has interesting parallels to Black Swan though.
37. Mr. Deeds (2002)
PG-13 | 96 min | Comedy, Romance
A sweet-natured, small-town guy inherits a controlling stake in a media conglomerate and begins to do business his way.
Director: Steven Brill | Stars: Adam Sandler, Winona Ryder, John Turturro, Allen Covert
Votes: 152,420 | Gross: $126.29M
A remake of an old Frank Capra film, really just an excuse for a particularly lazy Adam Sandler vehicle. Winona, in one of her worst performances, flounders with the lame script and has zero chemistry with Sandler. Made around the time of her shoplifting debacle, so that year must have been a real annus horribilis for Winona.
38. The Dilemma (2011)
PG-13 | 111 min | Comedy, Drama
A man discovers that his best friend's wife is having an affair.
Director: Ron Howard | Stars: Vince Vaughn, Kevin James, Winona Ryder, Jennifer Connelly
Votes: 56,843 | Gross: $48.48M
39. The Last Word (I) (2008)
R | 90 min | Drama, Romance
A man (Bentley) who makes his living composing other people's suicide notes enters into a romance with the sister (Ryder) of a recent client.
Director: Geoffrey Haley | Stars: Wes Bentley, Winona Ryder, Ray Romano, Gina Hecht
Votes: 3,264
Winona is OK, but the script is quite insipid and the Ray Romano scenes are terrible.
40. The Informers (2008)
R | 98 min | Crime, Drama, Thriller
One week in L.A. in 1983, featuring movie executives, rock stars, a vampire and other morally challenged characters in adventures laced with sex, drugs and violence.
Director: Gregor Jordan | Stars: Billy Bob Thornton, Kim Basinger, Mickey Rourke, Jon Foster
Votes: 17,453 | Gross: $0.30M
Hardly anything happens in this film.
41. 1969 (1988)
R | 95 min | Drama, War
Two friends living in a small town during the 1960s, run away to enjoy their freedom during the Vietnam War, thus disappointing the father of one of them. When they return to town, they realize the importance of family unity.
Director: Ernest Thompson | Stars: Robert Downey Jr., Kiefer Sutherland, Bruce Dern, Mariette Hartley
Votes: 3,992 | Gross: $5.98M
Comedy-of-age drama that's a rather feeble attempt at portraying the hippy/Vietnam era. A forgotten entry in the early résumés of Winona, Kiefer Sutherland and Robert Downey Jr. Winona gets nothing to do.
42. The Darwin Awards (2006)
R | 94 min | Adventure, Comedy, Romance
To investigate bizarre insurance claims that transpired in either accidents, death or both, a former cop and an insurance investigator travel throughout the country to look at the cases up close.
Director: Finn Taylor | Stars: Joseph Fiennes, Winona Ryder, David Arquette, Ty Burrell
Votes: 10,436
Lame comedy flop which, like "The Ten", completely wastes an ensemble cast of good actors. Winona fails to make her character likable. Feels like it went straight to DVD and probably did.
43. Lost Souls (2000)
R | 97 min | Drama, Horror, Thriller
A Catholic teacher meets an atheist journalist, whom a group of Catholics and Priests believes has been chosen by the devil to be the Antichrist.
Director: Janusz Kaminski | Stars: Winona Ryder, Ben Chaplin, Sarah Wynter, Philip Baker Hall
Votes: 11,361 | Gross: $16.78M
Bleak, dull, highly forgettable satanic horror.
44. Boys (1996)
PG-13 | 86 min | Drama, Mystery, Romance
25 y.o. Patty is thrown off her horse and knocked out. Students from a boys' boarding school find her and smuggle her to John's room at the school as cops are looking for her at home.
Director: Stacy Cochran | Stars: Winona Ryder, Lukas Haas, John C. Reilly, James Le Gros
Votes: 3,837
Poor excuse for a film that Winona sleepwalks through in a state of delirium.
45. Haunted Mansion (2023)
PG-13 | 123 min | Comedy, Drama, Family
A single mom named Gabbie hires a tour guide, a psychic, a priest and a historian to help exorcise her newly bought mansion after discovering it is inhabited by ghosts.
Director: Justin Simien | Stars: LaKeith Stanfield, Rosario Dawson, Owen Wilson, Tiffany Haddish
Votes: 42,617
46. The Ten (2007)
R | 96 min | Comedy, Romance
10 stories, each inspired by one of the 10 Commandments.
Director: David Wain | Stars: Paul Rudd, Jessica Alba, Winona Ryder, Adam Brody
Votes: 16,969 | Gross: $0.77M
Terrible collection of unfunny, amateurish comedy sketches, only one of them raised a laugh from me thanks to Rob Corddry. Quite a few good and well known actors are in it but they are all wasted.
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