Winona Ryder: Her 10 greatest performances ranked, from Heathers to Black Swan

Winona Forever! An icon of outsider cool, Winona Ryder has mesmerised audiences for more than three decades. With The Plot Against America, her new limited series, launching on Sky Atlantic, Adam White revisits her 10 best performances so far

Winona Ryder in ‘Beetlejuice’, ‘Little Women’, ‘Heathers’, ‘Reality Bites’, ‘Black Swan’ and ‘Homefront’ (Rex/Shutterstock)

Few movie stars have inspired deeper reserves of goodwill than Winona Ryder. Whether you were a teenager in 1988 or 2020, different generations seem to have grown up with her.

Many fell in love with her in Beetlejuice, Heathers and Edward Scissorhands, where she radiated an insouciant cool that was as compelling as it was aspirational. Others discovered her later on DVD, those teen-movie touchstones passed down by parents and older siblings. Today’s teens, somewhat unexpectedly, see her as a quintessential maternal figure courtesy of her role in Netflix’s Stranger Things – those same contrasting qualities of strength and fragility transported into a different context.

After juicy cameos in Star Trek and Black Swan, it’s been TV where she’s found a second life (or is it third, or fourth?). This week she appeared in David Simon’s Sky Atlantic limited series The Plot Against America, inhabiting a striking supporting role that mirrors her recent turn in Simon’s similarly gloomy mini-series Show Me a Hero. It’s wonderful to have Ryder back and active again after an infamous arrest for shoplifting in 2001 unfairly derailed an impressive run of films (including Girl, Interrupted, Little Women and The Crucible) that brought her Oscar nominations and serious Hollywood clout.

To celebrate her new show, we’ve ranked her 10 greatest performances so far.

10. Homefront (2013)

It’s perhaps sacrilege to say that a forgotten Jason Statham movie features one of Winona Ryder’s best performances, but those rolling their eyes clearly haven’t seen Homefront. Made in the years between Ryder’s Black Swan-assisted comeback, and her more permanent Stranger Things-assisted comeback, it casts her as a backwoods gangster’s moll who swears and smokes and steals children. Ryder also steals the show, embracing the pulpy camp of a movie otherwise played far too seriously for its own good.

9. The Private Lives of Pippa Lee (2009)

Probably three people saw this 2009 drama, despite its A-list cast (including Robin Wright, Julianne Moore, Blake Lively and Monica Bellucci) and the fact that it’s one of a quartet of films to star both Ryder and her fellow Eighties pin-up Keanu Reeves (though they don’t interact here). It’s a shame, since Rebecca Miller’s melancholy drama also features one of Ryder’s funniest roles. In just a few scenes, Ryder fully captures a specific kind of moneyed self-involvement, where a lack of any real problems doesn’t prevent someone from being loudly, thoughtlessly dramatic about how terrible their life is. She’s an exhausting, crying-at-the-drop-of-a-hat hoot.

8. A Scanner Darkly (2006)

Ryder is animated here using rotoscope technology, which lends Richard Linklater’s Philip K Dick adaptation a sentient, acid-trip feel. Even through the visuals, though, Ryder is magnetic, sourcing a desperately sad vulnerability as a woman increasingly dependent on a hallucinogenic known as Substance D. The film saw Ryder and Reeves reunited 14 years after Dracula, and they have the melancholy chemistry of two mutually haunted souls.

Ryder and Keanu Reeves in ‘A Scanner Darkly’ (Warner Bros)

7. Little Women (1994)

This 1994 adaptation pales in comparison to Greta Gerwig’s transcendent one from last year, but Ryder is still brilliant. It also marked the second of her two back-to-back Oscar nominations, following the similarly bonnet-filled The Age of Innocence. What works best here is her unbridled sunniness and zest for life; Ryder’s is the softest, most winsome on-screen Jo March.

6. Reality Bites (1994)

Reality Bites is more of a time capsule than any other movie released in the Nineties; a Gen-X wormhole soundtracked by Dinosaur Jr and Lisa Loeb that even features Gap as a major plot point. It’s also the clearest distillation of Ryder’s early appeal – the pixie cut, the to-and-throw uncertainty about life, the stroppy, chain-smoking ennui. As a directionless twenty-something fresh out of college, she is radiant, delivering a pure-movie star performance of unambiguous chic.

5. Black Swan (2010)

If phase one in Ryder’s post-arrest comeback didn’t quite resuscitate her career (did anyone see The Informers or The Darwin Awards?), then Black Swan certainly did, reminding everyone of what we briefly lost. Darren Aronofsky’s ballet horror movie is a wonderful car crash of tones and genres, but somehow Ryder still stands out, even if she barely features. In a deliberate piece of meta-casting, she plays a faded dancer phased out of the business by Natalie Portman’s baby-voiced upstart. A seething, wild-eyed mass of resentment, she is terrifying to watch, her brief appearances plunging the film into further chaos.

4. Girl, Interrupted (1999)

Girl, Interrupted was Ryder’s last true starring role in a major movie, and was also the film that catapulted Angelina Jolie into the A-list. The loudness of Jolie’s performance slightly overshadowed what is one of modern film’s most glorious ensembles (Brittany Murphy, Whoopi Goldberg, Elisabeth Moss and Vanessa Redgrave are luminous here), and, in all honesty, it’s Ryder who holds it all together. She’s a student in Sixties New England admitted to a psychiatric hospital after a suicide attempt, and her performance burns with a skittish, rail-thin anxiety. Perhaps it gets overlooked because it’s classic Ryder – drifting, literary, quietly self-destructive. Just because she does this a lot, though, doesn’t mean it isn’t still masterful.

Ryder and Gena Rowlands in ‘Night on Earth’ (Rex/Shutterstock)

3. Night on Earth (1991)

Ryder and Gena Rowlands sparkle together in the first vignette of Jim Jarmusch’s anthology film about random encounters in taxi cabs. Ryder plays taxi driver Corky like a lumbering teenage boy, tossing Rowland’s bags in her car as if they’re soft toys, and hurling Bart Simpson-style insults at passing motorists (“Try driving school, nimrod!”). Rowland, playing a Hollywood casting agent, can’t stop herself from being completely mesmerised by this girl, convinced she has what it takes to be a movie star. In fairness, she has a point.

2. Beetlejuice (1988)

Lydia Deetz, the proudly “strange and unusual” teenage girl Ryder plays in Beetlejuice, is still incredibly special. She is an oddball pioneer, the blueprint for every fictional teenage girl far smarter than the adults around her, and an inspiration for everyone who was performatively obsessed with death and misery when they were 15 and lonely. In her wake emerged Angela Chase, Daria Morgendorffer and Veronica Mars, snarky burnouts who revel in their ingenuity, empathy and sheer outsiderness. It’s arguably Ryder’s most beloved role, and therefore even more impressive that it didn’t trap her. She remains synonymous with goth glam, but quickly made sure we knew it was just one string to her bow.

1. Heathers (1989)

In an era of teen movies where Porky’s was king, only a 17-year-old Winona Ryder seemed to get Heathers. While much of young Hollywood, including Jennifer Connelly and Jason Bateman, turned the film down, or their parents banned them from starring in it (poor Heather Graham had the right name and everything!), Ryder understood its tone and the genius of her character Veronica Sawyer. She’s someone who alternates between striving to be the popular girl and wanting to burn the whole place to the ground. In effect, she’s a less kid-friendly Lydia Deetz, a teenager equally as strange, but entirely self-aware about how hard it is to not conform. Ryder is all things in this movie: angry, compliant, yearning and joyful. It cemented her not only as the coolest girl in Hollywood, but an icon for weirdos everywhere.