Fans of films from the 1990s will gladly recall a time when Winona Ryder was one of the most bankable stars on the planet. Since her breakout roles in “Beetlejuice” (1988) and “Heathers” (1989), the actress enjoyed a steady rise to film stardom courtesy of her pointed ability to deliver dry wit, emotional vulnerability, and deeply flawed human beings, sometimes all in the same character.

While her Hollywood career was hindered by the negative publicity that followed a 2001 shoplifting incident—the kind of attention that’s usually only lobbied at famous women rather than men—Ryder has since enjoyed many a career renaissance, be it as a disgruntled former ballerina in Darren Aronofsky’s “Black Swan” or as the mother of ‘80s children on “Stranger Things,” a role so fittingly apropos. Here we’ve outlined 10 of her best movie performances worth watching.

10. Mr. Deeds (2002)

The 10 Best Winona Ryder Movies - Mr. Deeds (2002)

It might have been the bottom of the barrel regarding roles with substance for Ryder, but her performance in the Adam Sandler vehicle “Mr. Deeds” is still memorable over two decades later. While one can’t usually say much for Sandler films due to their overreliance on white heterosexual male humor, “Mr. Deeds” still stands out in both his and Ryder’s filmographies—primarily due to her commitment to the part. She plays tabloid journalist Babe Bennett, who disguises herself as a school nurse named Pam Dawson in order to gather dirt on Longfellow Deeds, who has recently inherited an estate worth $40 billion. What follows is Bennett falling for the small-town charm of Sandler’s character. Far from her most sophisticated role, Ryder is still the film’s best part.

9. Autumn in New York (2000)

The 10 Best Winona Ryder Movies - Autumn in New York (2000)

Often mocked and derided as some of the worst work of Ryder and co-star Richard Gere, “Autumn in New York” is unfairly criticized. Sure, does it make horrible use of the overused tropes of silver fox falling for a twentysomething woman, a woman who happens to be dying from a terminal illness? Yes, and yes. But what “Autumn in New York” often takes the most hits for is the supposed lack of chemistry between Ryder and Gere, which is most assuredly false. If there is ever a moment in the film where the characters lack chemistry, it is the script’s fault and not the actors. Indeed, the screenplay is nothing that would ever make history books, but there are so few instances where Ryder gets to show off her knack for adult roles in modern-day romances, and “Autumn in New York” is one of them.

8. Black Swan (2010)

The 10 Best Winona Ryder Movies - Black Swan (2010)

Not quite sure this can be classified as a Winona Ryder film since she’s only in it for all of one scene, but for a once highly bankable star who was relegated from box office star to independent supporting player in the 2000s, “Black Swan” was the perfect moment both personally and culturally for the actress to make a reappearance in a box office smash. A film like “Black Swan” reads ostensibly different in light of the #MeToo and Time’s Up movements, a fact that is especially true for Ryder’s character, Beth MacIntyre. Her most memorable line in the film happens to be, “Did you suck his cock?” in reference to Nina’s (Natalie Portman) sudden rise to fame as her ballet director’s new protégé. The character is then said to have been hit by a car and killed in what some believe to be a suicide attempt. MacIntyre’s career clearly suffered due to being groomed by Nina’s director before her, something that can also be said for Ryder herself in light of a shoplifting incident she attributes to a poor period of mental health. In short, few other actresses could have made such an impact for a seemingly minor part in “Black Swan” as Ryder.

7. The Crucible (1996)

The 10 Best Winona Ryder Movies - The Crucible (1996)

Ryder did many a period piece during the height of her film stardom in the 1990s, and “The Crucible” is the most underrated of the bunch. Based on a play by Arthur Miller that lightly fictionalizes the Salem witch trials of 1692, Ryder co-stars as young Abigail Williams, a girl who attempts to conjure love spells in the woods with her friends. On one such fateful evening, she wishes for John Proctor’s (Daniel Day-Lewis) wife, Elizabeth, to die so she might have John all to herself. The girls’ attempts at witchcraft might have gone unnoticed if it weren’t for her cousin Betty falling unconscious from the ordeal. As John and Abigail have engaged in an affair, John is falsely accused of witchcraft. Day-Lewis occupies most of the screen time in “The Crucible,” but Ryder’s supporting performance as a young woman who schemes to protect herself and her family from her actions is gripping to watch.

6. Reality Bites (1994)

The 10 Best Winona Ryder Movies - Reality Bites (1994)

Life is always funnier when it’s happening to someone else, right? In one of the most quintessential romantic comedy films of the ‘90s, Ryder stars as Lelaina Pierce, a recent college graduate, and valedictorian who is suddenly left to grapple with the realities of adult life when hers starts to go sideways. Ethan Hawke plays her male best friend Troy Dyer, the epitome of the brilliant but tortured young man who doesn’t know how to apply himself. Other co-stars include Janeane Garofalo and Steve Zahn as their fellow foundlings. As Ryder was riding high on the success of the period films “The Age of Innocence” and “Little Women,” she actively sought out a role set in the present day, and that happened to be “Reality Bites.” Not since “Heathers” had we been treated to the comic naivety and self-assurance that Ryder can genuinely express. While “Reality Bites” was conceived as being about the trials and tribulations of Generation X coming of age, it’s remarkable how well it’s aged into the 21st century.

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5. Beetlejuice (1988)

The 10 Best Winona Ryder Movies - Beetlejuice (1988)

Arguably the role that started it all. The self-described strange and unusual Lydia Deetz would become so ingrained in the culture of ‘80s films that it’s almost comical to imagine Ryder in the more adult parts she would pursue soon thereafter. Stuck as the only person who can see the ghosts that still inhabit the house her family has just bought in New England, Lydia ends up betrothed to the bio-exorcist  Beetlejuice, who claims he can free the ghosts once and for all. It’s spooky, it’s campy, it’s Tim Burton, and it’s a classic in its own right.

4. The Age of Innocence (1993)

The Age of Innocence (1993)

Perhaps the most cerebral of Ryder’s films was the romantic period drama that would bring her first Academy Award nomination in 1994. The film itself is more obsessed with its own cinematography and costumes than its screenplay, but there’s no denying that Ryder steals every scene in “The Age of Innocence.” If it weren’t for the comparatively lighthearted “Reality Bites” and “How to Make an American Quilt” that would follow, Ryder would have likely been permanently pigeonholed as a period drama star who was capable of little else. Forget the rebellious youths she played early in her career, period remakes, and adaptations of famous novels that, for the most part, lived and died in the 1990s would have been all she could have done. But Ryder’s talent possesses the versatility to transcend the cultural conversation, for better and for worse.

3. How to Make an American Quilt (1995)

How to Make an American Quilt (1995)

Often lost in the mix of “Little Women” and “Reality Bites,” the 1995 adaptation of Whitney Otto’s bestselling novel is simultaneously one of Ryder’s most vital and underrated performances. She stars as a young woman named Finn in the throes of finishing a thesis and thinking over a marriage proposal, stumped by how restrictive the options still appear for a woman of her age, even in the ‘90s. She spends the summer at her grandmother and great-aunt’s house, as she did as a child, where she is told about the loves and losses of their own lives and those of their closest friends. For a star with as much box office power as Ryder at this point in her career, she was possibly the only actress who could have played Finn as effectively as she does in “How to Make an American Quilt.”

2. Heathers (1989)

Heathers (1989)

Cult films become cult films for a reason. If the legacy of “Heathers” today is that it paved the way for the success of every offbeat young adult comedy film that would follow it, then more than half of that should be attributed to Ryder’s performance. A young Christian Slater does shine as a teenage psychopath who draws Ryder’s character into his orbit. Still, it’s Veronica whose image and portrayal would give “Heathers” the classic quality it retains today. It’s odd watching “Heathers” for the first time as a high school film made a decade before the Columbine massacre, so it’s not a film that should be taken at face value. It’s a film whose dark and cynical dialogue must get under your skin to make the impression the filmmakers were going for in 1989.

1. Girl, Interrupted (1999)

Girl, Interrupted (1999)

Angelina Jolie rightfully received the Academy Award for Best Supporting Actress for her performance in “Girl, Interrupted,” but Ryder’s performance deserves the same amount of high praise. Reminiscent of the teenager she played a decade earlier in “Heathers,” Ryder’s portrayal of Susanna Kaysen and her stay in a psychiatric hospital in 1960s America is as relevant today as the memoir on which the film is based. In the same way that few other actresses in the 1990s could have played Finn Dodd or Lelaina Pierce, it’s nearly impossible to imagine any other actress screaming, “What the fuck is going on inside my head?” from a bathtub to Whoopi Goldberg. Continue to give Jolie the acclaim she deserves for her astounding portrayal of sociopath Lisa Rowe. But don’t forget to give Ryder her due for “Girl, Interrupted” as well.

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