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Every Winona Ryder Movie Ranked Worst To Best

One of the stars of Netflix's hit sci-fi horror drama "Stranger Things," Winona Ryder got her start as a teen starlet in the late '80s, appearing in coming-of-age dramas and later, dark comedies. She would go on to become a Generation X icon in the '90s for iconic roles in movies like "Reality Bites" and "Girl, Interrupted." 

Early in her career, she was at her best playing quirky, socially awkward outcasts, which made her a favorite of eccentric director Tim Burton, who cast her in two of his best-loved movies. She would also take on similarly-styled roles in films like "Heathers" and "Mermaids." Famous for sporting a short pixie cut, her wide brown eyes, and her brooding persona, Ryder matured into period dramas, as well. Films like "The Age of Innocence," "Little Women," and "The Crucible" proved could do more than play contemporary misfits. 

Over the course of her decades-long career, Ryder has gone from teen heartthrob to serious dramatic heavyweight. She's crossed every genre, from romantic comedy to psychological thrillers, science fiction to big-budget franchise action movies. With a catalog spanning decades, we've made a list of every major movie in Ryder's filmography and ranked them worst to best. Think you know which one tops our list? It might surprise you.

36. The Letter

A supposed psychological thriller, the 2012 film "The Letter" stars Winona Ryder as Martine, a troubled playwright working on her latest production. As she writes, Martine begins to confuse fiction with reality, unable to tell the difference between the words on the page and what's actually happening around her. As she attempts to write and re-write her script, her mental state deteriorates, and she begins to doubt everything in and out of the play. James Franco co-stars as an actor who seems to delight in manipulating and torturing his fellow castmates. 

"The Letter" is overflowing with pretentious visuals and dialogue that feels more like a film school project than an actual Hollywood movie ... which makes sense when you learn that it was directed by Jay Anania, a professor of directing at NYU. A poorly written, cheaply produced, low-budget movie that feels like it was shot over a single weekend, it's likely that "The Letter" only got attention (and was likely only ever released) because it managed to snag a couple of big name actors for its otherwise thin cast. Unless you're a Winona Ryder super-fan, steer clear of this sloppy, low-rent film.

35. Lost Souls

Released just a year after the similarly themed "End Of Days," the supernatural thriller "Lost Souls" chronicles the story of a small group of true believers who try to convince the world that the Antichrist is going to be reborn on Earth. One member of the faithful, Maya Larkin (Wynona Ryder) — who was once possessed by The Devil himself but managed to survive — now works to stop him from returning in another host. She soon tracks the prophesied return of Satan to a man named Peter Kelson (Ben Chaplin), who also happens to be an author of popular crime fiction.

Kelson is skeptical, but a series of strange coincidences and dark omens change his mind, and now he and Larkin work together to stop the Antichrist from possessing him. A muddled, messy story that's not at all clever when it really needs to be, "Lost Souls" is full of trite, overdone supernatural tropes. This kind of story has been done before and better, but even the bad ones, like the Demi Moore film "The Seventh Sign," have more going for them. Despite a decent cast that includes John Hurt ("Snowpiercer") and Elias Koteas ("Chicago P.D."), there's very little worth watching here.

34. The Informers

Taking place amidst the drug-fueled glitz and glamor of early 1980s Los Angeles, the 2008 film "The Informers" boasts an all-star cast including Billy Bob Thornton, Kim Basinger, Mickey Roarke, Amber Heard, Rhys Ifans, Brad Renfro (in his last role before his tragic death), and, of course, Winona Ryder. The movie takes place amid the hustle and bustle of Hollywood, where musicians and actors are looking for more money, sex, power, and fame. The film follows a number of different characters — from a used-up, drug-addled rockstar to a promiscuous girlfriend — all trying to make it in Hollywood, and some just trying to survive it.

Though Ryder is as charming as ever in the film, the movie itself is a cobbled-together mix of clashing ideas and stories. Notoriously, "Superman Returns" star Brandon Routh filmed a part for the movie that was excised in which he played a vampire, adding a supernatural element to the movie that was removed, perhaps for the best. Though if it had remained, perhaps it would have at least added something unique and eyebrow-raising, which the rest of the movie definitely is not.

33. Stay Cool

A coming-of-middle-age comedy, "Stay Cool" tells the story of a struggling author who returns to his old high school nearly two decades after he attended to give a speech to the current year's graduating class. Being back home though, he's forced to look back at his life and his youth, confronting old past troubles like the school bully (Marc Blucas) and his unrequited crush (Winona Ryder), who just so happens to be married to that same bully. The film has all the classic '80s high school stereotypes — but this time by design — including the absent-minded principal (Chevy Chase) and the gay best friend (Sean Astin), in a story about second chances. 

With Jon Cryer in the cast and so many obvious homages, "Stay Cool" is a love letter and spiritual sequel to the works of John Hughes, but lacks the charm and innocence of movies like "Pretty In Pink" and "Ferris Bueller's Day Off." It might be worth watching for Ryder alone, but making her character the "prize" and a subplot involving a high school girl hitting on the thirty-something returning alumni is more than a little groan-worthy, and the jokes made out of those situations are even worse.

32. Boys

The teen drama "Boys" follows emerging, would-be star Lucas Haas ("Mars Attacks") as John Baker, a disillusioned young man attending a boarding school for boys. Just as he's finishing up his final year (and none too excited about the next stage of his life), everything is thrown into chaos when he finds a troubled teenage girl lying unconscious in a field. He soon discovers that her name is Patty Vare (Winona Ryder) and she is someone who is running from her own shady past. John gives her refuge by hiding her in his dorm, but this soon causes problems for them when they are found out, and they both must face up to what they've done and move into uncertain futures.

A promising concept and a decent cast that features some intriguing elements and good performances, "Boys" nevertheless disappoints with a style and tone that is never quite sure what it wants to be. At times, it's a teen comedy, at others an understated drama, and at others a compelling mystery, all while trying to blend some of the edgy style of other, better mid-'90s fare. Ultimately, the good gets lost and Winona Ryder is left alone in the middle of it all.

31. Autumn In New York

The 2000 romantic drama "Autumn In New York" stars Winona Ryder as Charlotte Fielding, a dreamy 22-year-old woman recently diagnosed with a fatal tumor near her heart. With less than one year to live, Charlotte has a chance encounter with the much older and more serious Will Keane (Richard Gere), and before they know it, the two are spending a casual night together. Their steamy one-night stand soon leads to a more serious relationship in spite of both of their reservations given their many differences and her impending death. The film follows their turbulent but brief relationship as they navigate the ups and downs of their love affair, and Will's recent discovery of a daughter he never knew he had. 

Overcoming both an age gap and infidelity, the relationship blossoms, and Will becomes determined to save Charlotte's life. Calling in favors, he arranges a risky heart operation just in time for Christmas. A tragic ending mixed with overtly sappy sentimentality makes for a mediocre movie, and while the cast does their best, the chemistry between Ryder and Gere is almost non-existent, which is an important ingredient in a romance like this one. In the end, it attempts to recapture the feel of Hollywood classics like "An Affair To Remember" or "Love Story," but it doesn't succeed.

30. Mr. Deeds

A remake of the classic 1936 comedy "Mr. Deeds Goes To Town," which was directed by Frank Capra and featured Gary Cooper and Jean Arthur, the 2002 movie "Mr. Deeds" instead stars Adam Sandler and Winona Ryder. The titular Longfollow Deeds (Sandler) is a man of simple living who runs a pizzeria and writes greeting cards in his spare time. When his billionaire uncle dies and he is left the lone surviving heir, he sells all the stock in his uncle's company and suddenly finds himself rich beyond his wildest dreams. 

Desperate to write the rags-to-riches story, intrepid reporter Babe Burnett (Ryder) masquerades as a local nurse to worm her way into Deeds' life, only to instead fall head over heels in love with him. But when the CEO of his uncle's company wants to sell the company and destroy his family legacy, Longfellow steps up to try and do the right thing. Babe, meanwhile, must work to win him back after he discovers that she had been lying about herself. A routine romantic comedy — albeit one with a twist ending — there's little to love. Sandler and Ryder are a far cry from Gary Cooper and Jean Arthur, and the critical consensus on Rotten Tomatoes notes that "this update of Capra doesn't hold a candle to the original, and even on its own merits, 'Mr. Deeds' is still indifferently acted and stale."

29. Sex and Death 101

"Heathers" screenwriter Daniel Waters re-teamed with star Winona Ryder for the 2007 black comedy "Sex and Death 101." Simon Baker stars in the film as Roderick Blank, a man on the verge of marriage who receives a strange list that notes all the women he's ever slept with, including his fiancée — at #29 — and an additional 72 names. Most interestingly, #30 is a woman he meets the night of his bachelor party, and he comes to believe that the list includes all the future women he'll be associated with, as well. Calling off his wedding, Blank decides to track down and work his way through every name on the list. It just so happens, however, that a mysterious serial killer (Winona Ryder) is at work in the city and is murdering men who've wronged her. When her identity is finally revealed, it's discovered that she is the final woman he's destined to sleep with. 

Believing he may be doomed to die by the woman's hand, he sets out to alter his fate, while also beginning to question his own motives in finishing the mysterious list. An intriguing concept, the movie doesn't quite live up to its compelling ideas, lacking the heart and earnestness it would need to become a classic like "Groundhog's Day" or "50 First Dates." Instead, it becomes little more than a clever rom-com turned unsatisfying slasher movie. Still, Ryder turns in a fun performance as the vigilante killer, even if it can't come close to the delightfully dark "Heathers." 

28. The Dilemma

It seems Winona Ryder is attracted to dark comedies, and she added another to her résumé when she appeared in "The Dilemma," a film directed by Ron Howard ("Arrested Development") that also stars Vince Vaughn, Kevin James, Jennifer Connelly, Channing Tatum, and Queen Latifah. The film is about two friends, Ronny and Nick (Vaughn and James), who are partners at an auto design business. Together they're working on a critical new project for a major car company that could make or break their fledgling firm. But while both are stressed about the impending project, Ronny spies Nick's wife Geneva (Ryder) kissing another man, Zip (Tatum). Finally deciding he should tell his friend, Geneva begs him to reconsider, promising the affair is over, while concerned that the trauma could imperil their upcoming deal.

But when Ronny learns that Geneva and Zip are still involved behind Nick's back, and Geneva threatens him, he has to get proof of their affair before she can turn the tables. While the cast and crew are all-star caliber, and the core elements for a classic comedy are there, "The Dilemma" is the perfect example of a movie that's less than the sum of its parts. A simple but effective set-up gives way to comic hijinks that fail to deliver the big laughs, with the stars all feeling like they're going through the motions. It's a likable, diverting comedy, but everyone involved deserved better than a forgettable romp.

27. The Darwin Awards

A broad ensemble cast that includes Winona Ryder, David Arquette, Joseph Fiennes, Julianna Margulies, Wilmer Valderrama, Juliette Lewis, Ty Burrell, and many more, assembled to tell stories inspired by the internet phenomenon known as "The Darwin Awards," which mocks people who have died during silly activities. It all starts with an oddball detective named Michael Burrows (Fiennes) who loses his job after he botches a case that allows a killer to go free. Burrows soon takes up a new job with an insurance company investigating unusual death claims alongside his jaded partner, Siri Taylor (Ryder). 

Filmed as a sort of found footage documentary from the perspective of a film student following Burrows on the job, we meet a number of unique individuals explaining how idiotic stunts and reckless happenstance led to untimely deaths. This includes a man who strapped a rocket to his car and a pair of friends who use dynamite while ice fishing. Meanwhile, Burrows comes close to winning the award for stupidity himself as they criss-cross the country and are caught up in madcap antics. He also gets a chance at redemption when he discovers the location of the killer he failed to nab before.

Though not the oddest source material for a movie, basing a film off of a comedy website and trying to tie it all together with a narrative may have been what doomed this one. Funny at times, other times a groan-inducing bore, "The Darwin Awards" is a bit too uneven and predictable to be one of Ryder's better films.

26. The Ten

Another film with an ensemble cast, "The Ten" is a series of vignettes, two of which star Winona Ryder. Written by David Wain and Ken Marino, the comedy anthology features ten different stories, each one inspired by one of the Ten Commandments from the Bible. Ryder stars in two of the installments, the first, which also features Adam Brody, is based on the first commandment, and titled "Thou Shalt Worship No God Before Me." In the short tale, a man falls from a plane and gets stuck in the ground, becoming a celebrity in the process. While he basks in the glow of idolatry, it costs him the love of his fiancée (Ryder).

 Later in the film, in the seventh story, "Thou Shalt Not Steal," Ryder's character from the first entry returns, having left her boyfriend, and is now married to a TV anchor. But when she meets a mysterious ventriloquist dummy, she falls in love and leaves her husband for a tawdry affair with the puppet. Choppy at times, some of the stories in this anthology work and others don't, making "The Ten" a hit-or-miss comedy. So, depending on your tastes, your mileage may vary, but Ryder's stories are definite highlights, especially if you're a fan of the actress.

25. Square Dance

The 1987 film "Square Dance" stars a young Winona Ryder as 13-year-old Gemma Dillard, an innocent and naive Texas farm girl who has lived with her grandfather (Jason Robards) ever since her young, unwed mother ran off. But when her mother resurfaces, Gemma reluctantly relocates to Fort Worth, where she struggles to adapt to the much more complicated life of the big city. There, she gets into trouble with her mother and befriends a young man with an intellectual disability named Rory (Rob Lowe), and their confused relationship causes problems for everyone involved.

A well-meaning family drama, it's an interesting look at Ryder's pre-fame career. There are some good performances and an interesting character study to be had, but not quite enough to make it one of the more memorable entries in the actress' filmography. It's not a winner, but if you like your coming-of-age dramas melancholy, and have a soft spot for Winona Ryder, this one should do it for you.

24. Alien: Resurrection

A superstar in the mid-'90s, Winona Ryder joined her first big franchise when she starred alongside Sigourney Weaver in the sci-fi action sequel "Alien: Resurrection." Unfortunately, it is not a classic like the first two stellar films in the series. Following the events of "Alien 3" that left series star Ellen Ripley dead, a military corporation clones her with a mix of blood samples from the original and DNA from a xenomorph. The new Ripley is more human than human with enhanced strength, agility, and reflexes, and is planned to serve as a new alien queen. A group of mercenaries arrives, including a young woman named Call (Ryder), who right away wants this Ripley clone dead to prevent new xenomorphs from being born.

But unbeknownst to the mercs, the aliens have already been bred, including a super-soldier alien hybrid that begins rampaging through the ship. Ripley and Call must put aside their differences to stop the emerging menace. A middling mix of monster horror and science fiction, "Alien: Resurrection" twisted the franchise a little too far. But viewed on its own merits, it's not all bad: the campy tone may not fit with the series, but it sort of works as a big-budget B-movie — if you can leave your expectations at the door — with some fun elements and good action to be had. Meanwhile, the dynamic between the Weaver and Ryder gives it a fresh angle for this kind of sci-fi slasher.

23. The House of the Spirits

"The House of the Spirits" is the 1993 period drama written and directed by Billie August that recounts the multi-generational story of a Chilean family during their country's most turbulent years. Starring Meryl Streep, Antonio Banderas, Jeremy Irons, and Glenn Close, the film is narrated by Winona Ryder as Blanca Trueba, the central character of the film, as she comes of age on a South American ranch. 

Surrounded by drama, her story begins with her father Esteban (Irons), an ordinary laborer who falls in love with the daughter of a wealthy man. Determined to be good enough to marry her, Esteban sets out to make his own fortune. After their marriage, Blanca is born, and we follow her struggles growing up and falling in love with a peasant named Pedro (Banderas), a relationship that her father does not approve of. We follow Blanca into adulthood, as her father becomes part of the revolution leading him into direct conflict with Blanca's lover, who controls the opposing party. As Esteban's side succeeds in a coup, Blanca and Pedro are persecuted and must escape their homeland if they want to survive.

Though a disjointed melodrama, Ryder may be the highlight of the film, delivering a powerful performance as Blanca through her troubled life.

22. Welcome Home, Roxy Carmichael

Off the back of "Beetlejuice," where she played dark and brooding Lydia Deetz, Winona Ryder became the epitome of the '80s goth girl and played one again in her next film, "Welcome Home, Roxy Carmichael." The film puts Rider into the role of Dinky, an anxious teen whose awkward and anti-social attitudes alienate those around her ... which is just fine by her. A high school outcast, she relishes being a misfit and ignores the attempts by teachers and her parents to make her more normal. But Dinky was adopted as a baby and has since come to believe that her birth mother is Roxy Carmichael (Ava Fabian), a small-time celebrity actress who left town not long after Dinky was born.

When Carmichael is announced to pay the town a return visit, Dinky becomes obsessed, and digs up as much dirt as she can, even tracking down Roxy's old boyfriend who she comes to believe is her birth father. Willing to do anything to prove to the town that she's Carmichael's daughter, Dinky is convinced that the starlet is the answer to all of her problems and that the actress will whisk her away to a world that will embrace her uniqueness. Likable and watchable thanks to Ryder's offbeat performance as the quirky goth teen, it might not be a classic, but it could just be one of Ryder's most underrated films.

21. The Last Word

Not to be confused with the 2017 film with Amanda Seyfried of the same name, the 2008 drama "The Last Word" stars Winona Ryder and Wes Bentley ("Yellowstone"). Bentley plays Evan Merck, an idiosyncratic writer who makes a living anonymously penning poignant suicide notes for those in need of a poetic final statement. So successful is he that his work has been featured in magazines, with one earning a prestigious poetry prize. His latest client, however, changes his life forever. When Evan attends his funeral, he meets his client's free-spirited sister, Charlotte (Ryder). 

Charlotte immediately takes a liking to Evan, who lies about his relationship with her brother, and the two embark on a passionate affair as she seduces the odd but brilliant writer. As they grow closer, however, Evan finds it more and more difficult to keep his secrets from her, even as he works with a cynical new client (Ray Romano) on his next goodbye masterpiece. If you can accept the movie's inherently flawed plot device of a professional ghost writer of suicide notes, you'll find a macabre love story that does its job as an offbeat romantic black comedy, and shows how a talented actress like Winona Ryder can make something out of role that could have easily fallen flat.

If you or anyone you know is having suicidal thoughts, please call the National Suicide Prevention Lifeline​ at​ 1-800-273-TALK (8255)​.

20. Great Balls of Fire!

After making a big impression in "Beetlejuice" in 1988, Winona Ryder began her Hollywood ascent, and came back a year later to appear in the Jerry Lee Lewis biopic "Great Balls of Fire!" Starring opposite '80s leading man Dennis Quaid, Ryder played the rocker's young cousin Myra Gale Brown. The film depicts their disturbing relationship, which saw Lewis — at the height of his career — marry his then-13-year-old relative when he was in his 30s. The extremely problematic marriage is covered in detail in the movie, as is Lewis' difficult relationship with his manager (Alec Baldwin) and with the press, who discover that his bride is his underage cousin.

Damned in the papers as a child abuser, Lewis' career is destroyed, which only complicates things for Myra. A watered-down, sanitized version of the true story, the film doesn't touch on the extent of the actual abuse that Myra Gale Brown alleged she suffered at Lewis' hands in real life, and some have criticized the film for overly simplifying one of the biggest scandals in music history and nearly romanticizing the criminal relationship. But Ryder and Quaid give good turns, exploring the rarely seen seedy side of rock n' roll, even if it is diluted by Hollywood's need to tell a complicated story.

If you or someone you know may be the victim of child abuse, please contact the Childhelp National Child Abuse Hotline at 1-800-4-A-Child (1-800-422-4453) or contact their live chat services.

19. Destination Wedding

When the 2018 film "Destination Wedding" was released, it had been nearly 30 years since Winona Ryder first starred opposite Keanu Reeves, and in their fourth collaboration, we see just how far both actors have come since they were paired together in "Bram Stoker's Dracula." The underseen movie sees the two stars play Lindsay and Frank, a pair of strangers who annoy each other while waiting to board a plane, and then realize they are seated next to each other on their way to the same destination wedding. They then wind up booked into adjoining rooms and seated beside one another at the rehearsal. The two can't seem to avoid each other, continuing to not get along, and are on the opposite side of every argument, whether it's about life, love, or work. 

Of course, that tension quickly turns to attraction and the two spend a night together and eventually fall in love. But the commitment-phobic Frank wants no part of a relationship, and it's up to Lindsay to convince him they should be together. A cynical, dour comic romance with a pair of antisocial leads, it's often predictable and offers very little new to the genre. Still, "Destination Wedding" is a solid film with two fantastic veteran actors paired with a sharp script that has some bits of black comedy gold to be found. 

18. The Private Lives of Pippa Lee

"The Private Lives of Pippa Lee" explores the troubled past of its titular character (played by Robin Wright as an adult and Blake Lively in flashbacks). In the present, she's a well-respected woman who many look up to, including an idiosyncratic poet (Ryder) who sees her as the perfect wife and mother. Pippa is the doting partner to an older publishing agent, Herb Lee (Alan Arkin), whom she married as a young woman, leaving her wild youth of drugs and sex behind. The films follows Pippa and her husband as they work through hard times that nobody sees, including her affair with a much younger man (Keanu Reeves). But when Herb dies, Pippa removes the shackles of domestic servitude and returns to her free-spirited ways.

The indie drama boasts a stellar cast and tells a compelling personal journey. It's an interesting film that examines how we become different people all throughout our lives, and asks the question: Which one is really who we are? Though Ryder plays only a supporting role, it's an important one, and she makes the most of it, adding a bit of dark comedy to the proceedings.

17. The Iceman

A stylish thriller, the 2012 film "The Iceman" is a biopic of notorious murderer and hitman Richard Kuklinski, convicted of murdering at least five people during his criminal career. The film stars Michael Shannon ("Man Of Steel") as Kuklinski and Winona Ryder as his wife, Deborah, who never suspects that her husband is a ruthless killer. The film follows him from his abusive upbringing to his days working on pornographic films, and eventually, being hired to kill enemies of New York mafia man Roy DeMeo (Ray Liotta), who takes Kuklinski into his employ. As he gets further entrenched in mob violence, domestic bliss at home with Deborah deteriorates, as his wife and family become targets of those who want him dead.

In the end, an investigation by police into gangland killings leads to Kuklinski, who confesses to over a hundred murders, much to his wife's horror. It was Michael Shannon's chilling performance as the stone-cold Kuklinski that captured most critics' attention and made the movie so memorable. The Guardian gave the film three stars, praising it as a compelling mix between "Zodiac" and "Goodfellas." James Franco, Chris Evans, David Schwimmer, and Stephen Dorff round out the cast.

16. 1969

Led by Robert Downey Jr., Winona Ryder, and Kiefer Sutherland, the drama "1969" was released in 1988 and tells the story of three college-age kids in a small town who are grappling with the harsh realities of looming adulthood while the nation is embroiled in a controversial war. Sutherland and Downey Jr. play best friends Scott and Ralph, who watch as Scott's brother, Alden (Christopher Wynne), is sent off to fight in Vietnam, and Ralph's younger sister Beth (Ryder), graduates high school. But when Ralph becomes eligible for the draft, he and Scott make plans to spend what could be their last summer together traveling the road.

After Ralph is taken into custody for attempting to avoid service, Scott — who has long had feelings for Ralph's younger sister — invites Beth to come with him while he flees to Canada to ensure he doesn't end up in the same boat. On the way, the two fall in love, and eventually decide to head back home where tragic news makes them realize the importance of family. A box office bomb, it is the kind of well-made, coming-of-age drama that Ryder excels in. While it's not the best that the actress would ever make, it's another underrated film in her catalog that deserves another look.

15. How to Make an American Quilt

In 1995 Winona Ryder starred in the film adaptation of the novel "How to Make an American Quilt." Ryder took the lead role of Finn Dodd, a young woman who is proposed to by her boyfriend Sam (Dermot Mulroney). Shocked by the proposal, Dodd ponders whether to say yes, unsure if she is ready for marriage. As she ruminates on her decision, she visits her aging grandmother (Anne Bancroft), who is part of a group of women who make quilts together. During her visit, the women take turns telling Dodd their stories of life, love, and marriage: the ups and downs, the best and worst times in their lives. These women include Em (Jean Simmons and Joanna Going), who is married to a serial cheater, Constance (Kate Nelligan), whose husband died young, and Marianne (Alfre Woodard), who regrets the love she could never have. 

As the women weave their quilt, each square embodies their story, told in flashback. Claire Danes, Jared Leto, Maya Angelou, Kate Capshaw, and Ellen Burstyn round out the ensemble cast. A story about life and love, it's an uneven series of flashback tales propped up by a string of strong performances, and Ryder's central character's struggle to define true love.

14. Girl, Interrupted

A passion project for Winona Ryder, "Girl, Interrupted" is based on the memoir of Susanna Kaysen, a young woman who spent time in a psychiatric ward that treated patients living with clinical depression, obsessive-compulsive disorder, and anorexia. Published in 1993, Ryder herself attempted to purchase the rights to the book, which were eventually gobbled up by Hollywood producer Douglas Wick, who promptly partnered with Ryder on the film adaptation. 

Released in 1999, "Girl, Interrupted" explores Susanna's troubled youth as an outcast young woman who attempts to end her own life and finally agrees to admit herself for treatment in a psychiatric hospital. There, she meets a kind nurse (Whoopi Goldberg) and an out-of-control woman who is struggling with drug addiction (Angelina Jolie, in a star-making performance that won her an Academy Award), among many other memorable characters. A few years after the film's release, Ryder herself had highly publicized difficulties off-screen which culminated in her own treatment for anxiety and depression, adding a haunting layer to the story.

If you or anyone you know is struggling with addiction issues, help is available. Visit the Substance Abuse and Mental Health Services Administration website or contact SAMHSA's National Helpline at 1-800-662-HELP (4357). 

13. Mermaids

Adapted from the acclaimed novel, "Mermaids" centers on Charlotte Flax, an anxious teenage girl in the 1960s who, along with her younger sister (played by Christina Ricci in her feature film debut), has spent her childhood moving from town to town with their eccentric mother (Cher). After their latest relocation, the sheltered Charlotte befriends an older man, the caretaker at the convent that neighbors their home. Enamored with the man, the two begin a relationship that complicates things for Charlotte, as her interest in religion makes her fearful of her newfound feelings. 

At the same time, Charlotte's mother is having a new romance of her own with local shoe store owner Lou Lansky (Bob Hoskins). Together, the complicated mother and daughter duo must come to terms with their own pasts and futures. The film was met with strong reviews and Ryder, in particular, received praise for her performance. Noted critic Roger Ebert applauded the actress in his review for the Chicago Sun-Times, saying, "Winona Ryder, in another of her alienated outsider roles, generates real charisma." 

12. The Crucible

Hollywood's second adaptation of the Tony award-winning play by Arthur Miller, the 1996 film "The Crucible" follows a fictionalized account of the Salem Witch Trials that took place in Massachusetts in the 17th century. Originally written as an allegory for McCarthyism, the film reunited Winona Ryder with her "The Age of Innocence" co-star Daniel Day-Lewis, who plays John Proctor, a well-respected member of the community who is having an affair with his teenaged maid and house servant, Abigail Williams (Winona Ryder). A tangled mess of accusations of witchcraft, deadly lies, and community upheaval ensue as the personal and political clash in early colonial America. 

Much like the play on which it is based, "The Crucible" takes liberties with the historical account. However, the committed performances and engaging period details make this one well worth a watch. The film was well-reviewed for its thematically weighty tone and faithful take on Miller's original work.

11. Night on Earth

The 1991 indie drama "Night on Earth" is a series of short stories about cab drivers connecting with their passengers during each of their respective journeys. With vignettes set across the globe — in New York, Los Angeles, Paris, Rome, and Helsinki, Finland — writer and director Jim Jarmusch crafted a smart, clever comedy with a strong cast and quirky characters. In the film's first entry, Winona Ryder plays one of her most unexpected roles as Corky, a rough and tumble, cigarette-chomping Los Angeles cabbie who aspires to be a mechanic. During one fateful late-night fare, she picks up Victoria (Gena Rowlands), a powerful Hollywood executive who's on her way back from the airport. During the ride home, the two women bond despite the divide between their personalities and lifestyles, with Victoria eventually offering Corky a part in her next film.

The other four stories are equally as compelling with unique characters, well-crafted dialogue, and plenty of heart. With music and score by musician Tom Waits, "Night on Earth" becomes cinematic poetry, and shows how people can form connections across many divides both physical and otherwise. Though it's a mostly forgotten film today, it's a solid early '90s indie movie that deserves renewed attention.

10. Reality Bites

An iconic Gen X film, the romantic comedy "Reality Bites" encapsulates the ennui and frustration of a generation of youth that grew up under the specter of their proud and pushy Baby Boomer parents as their two vastly different cultures collide. The film stars Winona Ryder as Leilana Pierce, a would-be movie-maker who sets out to document the lives of her friends on video and is offered the chance to get it aired on TV by a hotshot executive (Ben Stiller). As Leilana follows the lives of her friends, we see the recent college graduates having problems with getting and keeping jobs, being frustrated in life and love, and being challenged to live up to the dreams set for them by a society they feel has left them behind. 

Once she assembles the footage of her friends and carefully crafts her documentary, Leilana must face her own disillusionment after it's chopped up and edited for television. In the end, she must also grapple with her own romantic struggles with her best friend, Troy (Ethan Hawke). Along with movies like "Singles" and "Empire Records," 1994's "Reality Bites" was the quintessential film for the jaded generation, and helped turn Ethan Hawke and Ben Stiller into movie stars.

9. A Scanner Darkly

Once again teaming with Keanu Reeves, Winona Ryder starred in an adaptation of the classic cyberpunk story from the mind of Philip K. Dick ("Blade Runner"). Written and directed by Richard Linklater and produced through the use of rotoscoped animation, the cast also includes Robert Downey Jr. (in one of his last roles before he suited up as Iron Man) and Woody Harrelson. The film is set in a dystopian future overrun by ever-present state surveillance in response to a deadly new hallucinatory drug called Substance D that has flooded the streets and addicted almost a quarter of the population. 

Bob Arctor (Reeves) is an undercover narcotics officer who uses a tech-based "scramble suit" to disguise himself as Fred, and purposefully becomes hopelessly addicted to the drug. While he lives a secret double life as both an addict and an investigator, he looks to find the drug's main supplier. Bob/Fred hopes he will eventually meet this supplier through his dealer, Donna (Ryder), who he is also romantically involved with. But when Bob's superiors order him to investigate a local junkie, he learns that his next target is also his drug-addled alter-ego, and suddenly his two lives collide and come crashing down as he's forced to hunt himself. A mind-bending sci-fi psychological drama, its unique visual trappings and all-star cast helped it become a stylish and provocative thriller.

8. Bram Stoker's Dracula

In a movie that includes several unlikely casting choices, Winona Ryder took on the role of Mina Harker in the 1992 adaptation "Bram Stoker's Dracula." Directed by acclaimed filmmaker Francis Ford Coppola, the movie stars Gary Oldman as the eponymous vampire, Keanu Reeves as Mina's husband, Jonathan, Tom Waits as Renfield, and Hollywood legend Anthony Hopkins as vampire hunter Abraham Van Helsing. A dark, foreboding take on the material, it's a faithful adaptation — less a monster movie than perhaps some earlier versions of the tale on the big screen — and was widely praised for its star-filled cast, lavish visuals, and gothic tone. 

Over the years, "Bram Stoker's Dracula" has become, for many, the definitive big-screen version of Stoker's masterpiece, with Esquire voting it high on the list of best vampire movies ever made. While Ryder delivers a strong turn as the object of Dracula's lust, and Hopkins also impresses, the film is all about Gary Oldman, whose towering performance as the sinister Count Dracula sits at the center, and went a long way to helping cement him as one of Tinseltown's most underrated talents.

7. Beetlejuice

In her career-defining role, Winona Ryder was cast in up-and-coming director Tim Burton's dark horror comedy "Beetlejuice" alongside Michael Keaton, Alec Baldwin, Geena Davis, and Catherine O'Hara. As the anti-social misfit teen Lydia Deetz, Ryder made her mark as the quintessential cool loner in black who is thrown headfirst into a fantasy world filled with nightmares beyond imagination. 

After the young girl is dragged to a new town by her overbearing, stuffy parents, Lydia discovers that her new home is no ordinary suburban haunt. In fact, the house is literally haunted by its previous owners (Baldwin and Davis), who want the newly arrived family gone. The ghostly couple ultimately turns to the mischievous monster spirit known as Beetlejuice (Keaton), much to Lydia's delight. She seems to get along better with the dead than anyone in the land of the living.

Before Burton's work on "Batman," "Edward Scissorhands" and "The Nightmare Before Christmas," "Beetlejuice" set the tone for all that would come next, and that includes his casting of Ryder as awkward goth girl Lydia Deetz. The film's unique visual style, outrageous antics, and bizarre story helped it become a cult classic and put both Ryder and Burton on the map. 

6. Experimenter

A dramatization of the Milgram Experiment — a series of controversial psychological experiments performed by researcher Stanley Milgram — the 2015 drama "Experimenter" stars Peter Sarsgaard and Winona Ryder as Milgram and his wife, Sasha. Intercut with the story of his life and marriage, we see Milgram developing and performing his experiments, testing whether his subjects — drawn from a cross-section of everyday people — are willing to do physical harm to complete strangers simply because they are told to do so by the person running the experiment. A study of obedience and authority that sent shockwaves through society, with its results being examined for decades, the study proved both informative and controversial, while nearly destroying Milgram's career.

A thoughtful and smart drama that delves deep into the psyche of the man behind the experiment, reviewer Godfrey Cheshire gave the film three and a half stars while calling it "the most pleasingly cerebral of recent American films." Using archival footage to supplement its dramatic reenactments, the film is an intellectual examination without the intense ratcheting stakes of more popular blockbuster biopics. Its reserved tone and analytical approach were apropos, but perhaps explain why the film was largely overlooked on its release. 

5. Black Swan

Director Darren Aronofsky's 2010 masterpiece "Black Swan" saw Winona Ryder return to a major Hollywood hit for the first time in nearly a decade, and helped bring her back to prominence after a string of small roles and poorly-received films. The movie stars Natalie Portman as Nina, a ballerina committed to landing the dual lead roles in a performance of Tchaikovsky's "Swan Lake." Winona Ryder plays a key supporting part as a washed-up, past-her-prime prima donna named Beth, who is pushed aside in favor of Nina. There is tension between the two dancers — one veteran, one rookie — as Beth lashes out at Nina in a memorably intense scene. 

But when a new, third dancer named Lily (Mila Kunis) enters the picture, things take a menacing turn. As Nina becomes more and more uncertain of her performance, she begins to spiral, and the lines between her dark inner world and reality start to blur. A sinister and effective psychological thriller, the film was nominated for five Academy Awards, with Natalie Portman winning best actress. Ryder, too, impressed in her smaller role, acknowledging that she related to her character's story as a veteran actress in Hollywood.

4. Heathers

A movie seen today as a classic, "Heathers" was a flop on its release in 1989, criticized for its dark, deeply cynical look at high school teens in the 1980s. Starring Winona Ryder, Christian Slater, and Shannon Doherty, the film is about a group of friends that included Veronica (Ryder) and three girls all named Heather. The four comprise a classic "mean girls" clique in their school, though Veronica is beginning to tire of the group. Their lives are all thrown upside down when an enigmatic bad boy named J.D. (Slater) moves to town. Fascinated by the dark-haired rebel, Veronica and J.D. soon become an item, while at the same time, the Heathers have ostracized her and vow to destroy her reputation.

As Veronica and J.D. grow closer, the rebel teen plots to destroy the Heathers. While at first, it seems like harmless fun, J.D.'s schemes quickly escalate to murder. Thought of today as a smart and successful black comedy, at the time, it was often described by its critics as a nasty, even cruel film. But over the years, thanks perhaps to the rise in stardom of its leads, "Heathers" worked its way up to become a Gen X cult classic.

3. Little Women

Early in her career, Winona Ryder seemed to love coming-of-age stories, and in 1994, she starred in perhaps the best-loved entry in the genre, "Little Women." Based on the literary classic by Louisa May Alcott, the movie is about a family of women: Jo March (Ryder) and her three sisters Amy, Beth, and Meg (Kirsten Dunst, Claire Danes, and Trini Alvarado), as well as her loving mother, Abigail (Susan Sarandon). It follows their trials and tribulations growing up in Massachusetts in the years just following the Civil War and explores their journeys from youth to adulthood. Throughout the film, the sisters fall in love and navigate the rivalries inside and outside of the family that complicate their lives.

The film was a critical darling, lauded for its interpretation of the beloved classic and mature take on the material, unlike previous versions that often turned the story into a wholesome family film or musicalRoger Ebert was likewise impressed, noting it as a "surprisingly sharp and intelligent telling ... and not the soft-edged children's movie it might appear." Its top-notch cast also includes Christian Bale, Gabriel Byrne, Samantha Mathis, and Eric Stoltz. "Little Women" even earned Winona Ryder her second Academy Award nomination

2. Edward Scissorhands

Following their work together on "Beetlejuice" Tim Burton and Winona Ryder reunited for "Edward Scissorhands" in 1990, the director's first film following his blockbuster success with "Batman." The film carries Burton's signature gothic tone and colorful, stylish visuals. He cast a young Johnny Depp as Edward, an artificial boy whose aging, eccentric inventor (Vincent Price in his final big-screen role) dies before he can give Edward human hands. Left alone in the inventor's remote mansion at the top of a hill, he is discovered by an innocent make-up saleswoman named Peg (Dianne Wiest). Taken in by Peg's family and plopped into a colorful, but banal suburbia, the scissor-handed Edward becomes a darling of the neighborhood, trimming hedges, making ice sculptures, and giving unique haircuts. 

But his crush on Peg's rebellious daughter Kim (Winona Ryder) causes trouble for Edward when her cruel boyfriend Jim (Anthony Michael Hall) tricks him into helping break into his father's home, turning the neighborhood against Edward. A movie that defies conventional description "Edward Scissorhands" is an uplifting tragedy, a dark romantic comedy, and a fantasy blending of different genres as only Tim Burton could do it. 

1. The Age of Innocence

In the mid-1990s, Winona Ryder appeared in a number of period pieces, from "Bram Stoker's Dracula" and "Little Women" to "The Crucible." In 1993, starred opposite Oscar-winning actor Daniel Day-Lewis in "The Age of Innocence," helmed by celebrated director Martin Scorsese. Based on the novel by Edith Wharton, the film is set in the late 1800s and tells the story of Newland Archer, a prominent and wealthy lawyer in New York City who courts a beautiful younger woman named May Welland (Ryder). But when May's socialite heiress cousin, the Countess Ellen Olenska (Michelle Pfeiffer), comes to New York after the end of her marriage, Newland finds himself distracted from his youthful and naive bride-to-be, and attracted to the more experienced and cultured relative.

The Countess eventually leaves New York, leaving Newland and May to wed, but her return years later complicates his domestic life when they begin an affair. A fanciful, classical romance, it was a throwback to films of the 1940s and '50s, made by Scorsese with a skill and craftsmanship rarely found in movies of its kind. For her part in the film, Winona Ryder received her first Academy Award nod, while the film itself received four additional nominations.