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, Winona Ryder has had a stunning transformation, going 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.

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.

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.

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.

"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." 

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.

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.

"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.

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)​.

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. 

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.

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.

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." 

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.

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.

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. 

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.

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 musical. Roger 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. 

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.