Few actresses are as synonymous with Gen-X excellence as Winona Ryder, and even fewer have managed to transform that generation’s sarcastic, disaffected, secretly yearning appeal into an enduring career. That’s because Ryder, for all her goth-princess beginnings in Beetlejuice and Edward Scissorhands, and her fuck-normalcy counterculture edge in Heathers and Reality Bites, has never been just an aesthetic.
Ryder’s reunion with filmmaker Tim Burton in Beetlejuice Beetlejuice is a celebration of her spooky allure and a recognition of how key her performances were to the director’s early filmography, but there’s so much more to Ryder than her ability to deadpan and how great she looks in choppy bangs. The actress has been delivering cunningly layered, unapologetically sensual, and exaggeratedly comedic performances for decades now. This woman has stolen scenes from Daniel Day-Lewis in two different period pieces! She deserves our respect! And here we are to give it to her, by breaking down 20 of her essential performances across movies and TV.
20.
Show Me a Hero (2015)
One of Ryder’s two collaborations with The Wire’s David Simon, Show Me a Hero is a true ensemble series; Ryder is just one part of a sprawling ensemble featuring Oscar Isaac, Alfred Molina, Jon Bernthal, Catherine Keener, and Clarke Peters. She doesn’t have a ton of screen time as Vinni Restiano, the Yonkers City Council president who advocated for integration of the city’s middle- and upper-class neighborhoods through low-income housing. But what she provides is a sense of steadiness — there’s a lot of political posturing, ambitious striving, and racist and classist hatred from the series’ other characters. In contrast, Ryder’s Restiano radiates sureness. You’ll look for her in scenes for that energy, which is a nice change of pace from the more flighty persona of her younger years.
19.
Destination Wedding (2018)
Ryder and Keanu Reeves have worked together numerous times and played love interests more than once, but Destination Wedding is perhaps the most straightforward version of that coupling: It’s a rom-com! The two bicker and banter and then fall into bed together! On paper, it should be pretty charming; in actuality, Victor Levin’s film is a little too woodenly written and a little too rotely directed, and, well, Reeves is playing an incel. But Ryder has always been great at falling in love onscreen, and although she and Reeves are both playing jerks, there’s still enough chemistry there to make you wonder when someone else will write a better, Ticket to Paradise–style flick for these two.
18.
Alien Resurrection (1997)
Alien Resurrection is not a particularly good movie, but it does feel like an omniscient one. Director Jean-Pierre Jeunet and writer Joss Whedon have more ideas than they know what to do with, but a few of those ideas — human experimentation, hybrid cloning, trying to “tame†the alien — would actually end up shaping the franchise for decades to come. Still, amid all this overstuffed plotting, Ryder has a nice action turn as mercenary and secret synthetic Annalee Call. She doesn’t do many films in this genre, but she handles herself well shooting at the aliens, running around the Auriga ship, avoiding acid blood, and projecting that slightly detached do-gooder vibe that the franchise’s synthetics are supposed to have unless their coding goes haywire. And while a seductively feral Sigourney Weaver as the human-Xenomorph queen clone Ripley 8 absolutely runs away with the film, her performance works so well because of Ryder’s wide-eyed affect as the skeptical, scared Call; the contrast between the two women, like in a scene where Ripley 8 tears out the internal second mouth of an alien and offers it to a disgusted Call as a “nice souvenir,†gives this film its personality.
17.
Drunk History, “Boston†(2013) and “Philadelphia†(2014)
Sometimes it’s nice just to watch Ryder have a little fun! She pops up in the first two seasons of Drunk History (RIP), and in each gives a performance that’s big, broad, and zany. In “Boston,†she plays Mary Dyer, a Quaker woman who was eventually hanged for her religious beliefs and for refusing to leave the Puritan-led colony that tried to banish her, and in “Philadelphia,†she plays Peggy Shippen, Benedict Arnold’s spy wife. Dyer’s story is a lot sadder than Shippen’s (in the latter, narrator Erin McGathy compliments Shippen more than once by calling her a cunt), but Ryder is lovely as each woman. As Dyer, she projects a confidence and capability that sparks well against Michael Cera’s hotheaded Puritan leader, and as Shippen — in a gigantic, Marie Antoinette–style wig — she’s just hilarious, mugging at the camera with shrugs and eye rolls even when she’s having missionary-style sex. It’s too bad that Drunk History was abruptly canceled during COVID, because Ryder is a great mime who certainly could have done more on the show.
16.
Beetlejuice Beetlejuice (2024)
Legacy sequel Beetlejuice Beetlejuice cycles through all the great moments from Tim Burton’s 1988 film (which, yes, ranks higher) without changing too much of the original’s formula. The Deetzes’ Victorian mansion still has the miniature of Winter River in its attic; Michael Keaton’s titular character is still gravelly voiced and gross; and the afterlife underworld is still a German Expressionist nightmare of bizarre angles and a jukebox playground of yesteryear pop hits. This is nostalgia bait, sure. But it’s undergirded by a consciously adult, steeped-in-sadness performance from Ryder, whose Lydia hasn’t had the best go of it in the nearly 40 years since her father and stepmother moved into this quirky, haunted town. She’s a reality-TV star who hates her job; she’s in a relationship with a man she’s only barely interested in; and she’s had to weather her daughter, Astrid (Jenna Ortega), never believing in her ability to see ghosts. Ryder plays the character as barely held together, gulping down pills and snapping at anyone who says the name of the demon who tried to marry her at the end of the first film. Lydia is emotionally battered, and Ryder makes us feel that in her combination of manic fear of Beetlejuice’s return and exhausted weariness when dealing with Astrid. When her stepmother asks Lydia “where’s the obnoxious little goth girl who tormented me all those years ago?,†we’re meant to sympathize with how much time has worn down Lydia, and we do. Beetlejuice Beetlejuice lets us feel the burden of nostalgia and what too much of it can do, and Ryder’s performance is central to that feeling of discomfort.
15.
Girl, Interrupted (1999)
Like Alien Resurrection, James Mangold’s Girl, Interrupted is another one where Ryder is overshadowed by a co-star, in this case, Angelina Jolie, whose mercurial performance rightly won her the Best Supporting Actress Oscar in 2000. But also like Alien Resurrection, Ryder is doing important work here as the straight woman for that flashier performance to play off of. She’s believable and pitiable as 18-year-old Susanna Kaysen, who, after a nervous breakdown and an overdose, ends up in the women’s ward of a psychiatric hospital. Girl, Interrupted leans a little too much on all of the other committed women having noticeable quirks or defining traumas (Susanna’s is the promiscuity caused by her borderline personality disorder), but Ryder is solid as a woman yearning to be liked and to belong to other people, and her performance blooms against those of Jolie, Brittany Murphy, Clea DuVall, and Elisabeth Moss. Ryder’s wide-eyed gaze gets overused, but that pixie cut really did open up her face.
14.
Friends, “The One With Rachel’s Big Kiss†(2001)
A few elements of this Friends episode, in which Ryder plays Rachel’s sorority sister Melissa Warburton, who meets up with her for the first time since college, haven’t aged well. The central tension of the episode is that Rachel insists she and Melissa kissed, and Melissa insists they didn’t — and Melissa’s “maybe I passed out and you did stuff to me while I was sleeping†getting a laugh-track response isn’t great. Some things are better left in the early aughts! But, of course, the two women did actually kiss, and Ryder’s comedic timing and physical performance sell that reveal. Her face melts when Rachel kisses her in the present to prove a point, and her body goes slack. Her voice gets hoarse and breathy when she says of the college kiss, “I think about it all the time,†and after Rachel rejects her come-on, it goes up a few octaves during Melissa’s panicked “Shut up!†Friends has tons of these little one-episode cameos, but not many of those guest actors did so much with so little as Ryder.
13.
Star Trek (2009)
The Star Trek cast weren’t complete nobodies in 2009 — Chris Pine, Zachary Quinto, Zoe Saldana, Karl Urban, and John Cho all had a few credits before signing onto the franchise reboot from director J. J. Abrams and writers Roberto Orci and Alex Kurtzman. But the ensemble needed an established face to help draw us in and establish narrative stakes, and as Spock’s human mother, Amanda Grayson, Ryder did that beautifully. Her gentle wisdom and unbothered love for Spock help soften Quinto’s super-constrained version of the character — like when she fusses with his uniform collar before his emotion-purge ritual and tells him whatever he chooses, “you will have a proud mother†— and Ryder plays her with such poise and dignity that her tragic death is probably the most impactful moment of that whole trilogy. This is the role that feels most like a warm-up for the maternal warmth Ryder would eventually exude on Stranger Things, and she adds exactly the humanity Star Trek needs to feel like a worthwhile new version of a story whose beats we already know.
12.
The Plot Against America (2020)
It’s rare for Ryder to play a true villain, but in The Plot Against America — her second collaboration with Simon, who has described her as having “the standing of the great American ingénue†— she comes pretty close. In the alternate-history miniseries based on the 2004 novel by Philip Roth, Ryder plays Evelyn Finkel, a Jewish woman who falls in love with John Turturro’s Rabbi Bengelsdorf. Out of self-loathing, a desire for power, or some other mysterious reasoning, the rabbi is a collaborator with the antisemitic administration led by aviator turned president Charles Lindbergh, and as his relationship with Evelyn deepens, she gets pulled into that hateful project, too. Ryder plays Evelyn as a woman so deep in love that she can’t see the consequences of her actions: She’s so head over heels for Bengelsdorf and so captivated by the elite worlds he pulls her into that she nearly immediately lets her own definition of Judaism and Jewish identity be pulled into his. Over six episodes, Ryder walks an impossibly thin line between vulnerability and selfishness, until finally, when it’s too late, she realizes the gravity of what she’s done in separating children from their parents, rubbing shoulders with Nazis, and forcibly relocating Jewish families. You’ll hate Evelyn, but Ryder makes it so you also can’t help but feel awful for her, and for what the madness of love will make you do.
11.
Stranger Things (2016-present)
Perhaps the role that skews closest to Ryder’s own real-life spontaneity, battery-bunny energy, and exasperation with the youths, Ryder’s Joyce Byers is — like her Amanda Grayson in Star Trek — the character who draws us in because of our nostalgia and our recognition, but keeps us coming back to feel her raw emotion. As the desperate and demoralized single mother searching for her missing son, Will, Ryder’s performance in the first season of Stranger Things is crystal clear in its angst, grief, and trauma, and all of the character’s quirks are in service of that. Her flightiness and her paranoia, her shrillness and her brusqueness — they all combine to help Joyce feel fully realized from the first episode. The series’ increasing scale and globe-trotting in its following seasons unfortunately resulted in Ryder being sometimes siloed from the main action; so many of her romantic-relationship beats and her obsessive concern for Will feel like regurgitations of her season-one arc. But there’s a reason why Stranger Things’s most defining image still is Joyce in her living room, surrounded by Christmas string lights she’s using to communicate with her missing son. That’s when the show’s emotional devastation felt most real and its fantastical possibilities most exciting, and Ryder was the reason why.
10.
Reality Bites (1994)
Maybe it is blasphemous to place Reality Bites on the outer edge of the top ten, but isn’t this a sign of how stacked Ryder’s career actually is? Reality Bites is arguably Gen X’s most defining film (no matter how much star Janeane Garofalo resists that description), and Ryder’s performance as aspiring documentarian Lelaina Pierce is a wondrous thing, all lit up from the inside with the glowing potential and prickly edges of Ryder’s youth. She’s all at once an ideological purist and a phony, a romantic and a cynic, and Ryder was more than skilled enough to guide Lelaina through the minefield of so many contradictions. Her relationship with Garofalo, as her best friend, Vickie, was joyous; her sexual tension with Ethan Hawke’s aspiring musician, Troy, was hot; and her sarcastic “What’s money to an artist?†during one of Troy and Lelaina’s fights was an all-timer of a line delivery. She was a hypocrite, but she was our hypocrite!
9.
Black Swan (2010)
Ryder is basically only in one scene in Black Swan, and man, does she make it memorable. As Beth, the New York City Ballet prima ballerina forced into retirement so that Natalie Portman’s upstart, Nina, can take over, Ryder is essentially a jump scare, a makeup-smeared woman lurking on the edge of Nina’s vision who hissingly calls her “such a frigid little girl†and waves her drink around like a weapon. Her facetiously toasting Nina with a derisive “You make the most of it, Nina!†is the film’s only laugh-out-loud moment, and it’s a welcome one. The film treats Ryder’s Beth as the evil hag witch who the virginal hard worker Nina has to beat to achieve her dreams, and Ryder plays that role with relish and gusto. More opportunities for Ryder to play an old-dame bitch, please!
8.
Beetlejuice (1988)
Ryder was 15 years old when she filmed Beetlejuice, but what remains so astonishing about her performance decades later is that there’s no precociousness or artifice to it, no overly cutesy adolescent quirks. She doesn’t play young, although she actually was young. Instead, Ryder’s goth-teen Lydia Deetz is just effortlessly cool, a shrugging mass of black fabric, powder-white makeup, and choppy bangs who oozed disinterest in her yuppie father and stepmother and legitimate fascination with the Maitland couple haunting the Connecticut Victorian mansion into which her family has just moved. As ghosts, Alec Baldwin and Geena Davis help us understand the world of the undead, but Ryder’s Lydia helps us understand the world of the living and why humans can choose to be so closed off or ignorant of the paranormal and spectral. She handles that responsibility well, giving the film some of its most memorably wacky moments — her delighted floating-in-air dance to Harry Belafonte’s “Jump in the Line (Shake, Señora)†— and holding her own against Michael Keaton’s Beetlejuice. Every expression she makes when he tries to forcibly marry her in the film’s final act is perfect; has anyone ever possessed so many different kinds of disgusted smirks?
7.
Little Women (1994)
As aspiring writer Jo March, Ryder perfectly embodies all the independence, hopefulness, and ambition of Louisa May Alcott’s iconic protagonist; she is, as your grandparents might say, “spunky.†Ryder keeps all of Jo’s defining qualities in perfect balance, from her slight superiority because of her writing talent, to her selfless support of her sisters, to her frustration with other people not accommodating her dreams and desires, to her not-love for brother-figure Laurie (Christian Bale). Jo can sometimes read as too much, but Ryder tempers that extra-ness with physical economy that allows us to understand the effort Jo takes to connect with and not disrespect others: how still she stands when Laurie kisses her against her will, how she lovingly pages through the books in her future husband Friedrich’s (Gabriel Byrne) office. She might not have gotten a “Women!†meme moment like Saoirse Ronan’s version of the character in Greta Gerwig’s adaptation, but Ryder inspired a generation of nerdy and independent-minded young women in her own right. Rory Gilmore wouldn’t exist without her.
6.
A Scanner Darkly (2006)
One of Richard Linklater’s most groundbreaking films visually, A Scanner Darkly improved on the rotoscoping technique the director started using in his previous film, Waking Life, and also gave Ryder one of her most complex roles to date. The adaptation of Philip K. Dick’s same-named 1977 novel is, admittedly, a film that demands multiple viewings, since it deals with double and triple identities and a piece of technology called a “scramble suit†that changes how characters look. You gotta pay attention! Ryder, though, is a grounding force here, playing a woman named Donna who is addicted to a popular drug named Substance D and who tentatively starts a relationship with Keanu Reeves’s Arctor; unknown to her, he’s an undercover cop trying to figure out who her dealer is, but she has motivations of her own, too. To say more about the plot would spoil the film too much, but Ryder is really a chameleon, flickering between quiet melancholy, genuine affection, and darker, more selfish concerns, and the rotoscoping art style accentuates the expressiveness of her face. A moment when she and Arctor clasp hands as they talk about the future, only for her to let go first, is gorgeous and despondent in equal measure.
5.
Edward Scissorhands (1990)
I dare you to watch the scene where Johnny Depp’s titular character carves an angelic figure modeled after Ryder’s Kim from a gigantic block of ice, creating flakes of snow that Kim dances under, and not feel like your heart is tearing in half. This is the movie that cemented Ryder’s status as a goth icon (and the first she made with Depp, whom she dated for four years and was engaged to for three of them), and this scene is perhaps Ryder at her softest — her twirling under the snow communicating a sense of wonder, and the smile on her face conveying that she knows she’s loved. (Director Tim Burton smartly keeps his camera on Ryder’s face as she whirls, and lets her beatific joy take up the frame.) Of course, nothing would ever be that happy again in Edward Scissorhands, and it’s a beautiful, shattering moment.
4.
The Crucible (1996)
The second of Ryder and Daniel Day-Lewis’s collaborations, The Crucible — written by Arthur Miller, adapting his own 1953 play — revolves around Ryder’s performance as teenager Abigail Williams, whose accusations of witchcraft against her neighbors in 17th-century Salem are fueled by jealousy, hysteria, and spite. This performance came years after Bram Stoker’s Dracula and The Age of Innocence, so it wasn’t a surprise that Ryder could be so conniving, cunning, and sensual as Abigail, whose romantic obsession with former lover John Proctor (Day-Lewis) fuels her to start making up lies about the devil communing with Salem’s residents. But she shows a powerful command of language in The Crucible, injecting lust, megalomania, and contempt as required, and she does well in the many toe-to-toes with Day-Lewis that the script demands. Her little smirk at Day-Lewis’s commanding “You will never cry witchery again†is simultaneously adolescent and threatening, which is one of the modes Ryder did best in her 1980s and ’90s early career.
3.
Bram Stoker’s Dracula (1992)
Sometimes you gotta writhe around in a diaphanous nightgown while sucking blood off an ancient vampire’s chest, you know? Francis Ford Coppola’s film is so maximalist and melodramatic that it’s easy to get lost in just how luscious this thing looks — Eiko Ishioka’s animal-inspired and historically influenced costumes, Dante Ferretti and Thomas Sanders’s extraordinarily detailed production design. But to focus only on the aura and atmosphere would be a disservice to Ryder’s dual performance, which drives everything in the movie. Ryder plays both Vlad Dracula’s wife, Elisabeta, who dies by suicide when she mistakenly hears that he’s been killed in battle, and 19th-century well-to-do woman Mina Murray, the wife of Dracula’s solicitor with whom he becomes obsessed, believing that she’s Elisabeta reincarnated. As Elisabeta, she has to make enough of an impact for us to understand Dracula’s renouncing of God and embrace of vampirism to deal with his grief, and as Mina, she has to be beguiling and pure enough to make Dracula leave the sanctity of his castle to pursue her, and Ryder easily does both. Her performance is the film’s emotional core; through her innocence, we understand what humanity has to offer, and through her corruption, we understand the depths of what Dracula has lost. The fluidity with which Ryder goes from standoffish when she first meets Dracula, to full-body horrified when he tries to feed on her for the first time, to her eventual eroticization and overwhelming desire as he begins to turn her into a vampire, is phenomenal. This was Ryder’s first grown-up role, and she made the transition with seemingly no effort at all.
2.
The Age of Innocence (1993)
This is Ryder in stone-cold-killer mode, and she excels at it. Martin Scorsese’s adaptation of Edith Wharton’s 1920 novel is one of his absolute best films; between this and Coppola’s Bram Stoker’s Dracula, we really were feasting in period-piece aura and atmosphere in the early ’90s. The Age of Innocence is primarily about a love triangle between wealthy New York City lawyer Newland Archer (Daniel Day-Lewis), his younger, seemingly naïve and vacuous fiancée, May Welland (Ryder), and her more worldly, sophisticated, unconventional older cousin Countess Ellen Olenska (Michelle Pfeiffer), but the film — as with all of Scorsese’s work — quickly becomes an allegory for the American experience at large, about how the strictness of social conventions and public propriety stifle the individual. The film’s heat is within Day-Lewis and Pfeiffer, who are so unbelievably sexy together that a simple hand caress feels pornographic. It’s Ryder, though, who demonstrates an ability for precise cruelty; a scene where she dominates an archery competition, shooting arrow after arrow into a bull’s-eye target, is an indication of her yawning need for control and perfection. Every accommodating smile feels barbed, every curtsy an attack, every look of serene placidity a mask. The politeness with which she tells Newland that she’s “afraid you can’t†travel to Europe to see Ellen again after she flees New York is a knife in the gut; Ryder is solely responsible for the film’s tragic final act, and she nails it.
1.
Heathers (1988)
The Ryder performance that has been often imitated, that influenced countless teen movies to come, and that has never been replicated in its verve or confidence. From director Michael Lehmann and writer Daniel Waters, Heathers is a bona fide classic, the black comedy that jettisoned Ryder and her co-star Christian Slater into the upper tiers of teen fame and also crystallized their unique appeal. So many of the qualities we associate with Ryder still — smart, sassy, scoffing — are born in this performance as self-loathing popular girl Veronica Sawyer, in her precise comedic timing while trading barbs with Slater’s J.D. and in her exhausted weariness with her frenemies the Heathers. Heathers has been redone in the years since (a musical, a TV series), but they’re just not the same without Ryder as Veronica, the cynic who eventually grows a soul (and grabs the friend group’s totemic red scrunchie for herself). Plus, no one has ever made a monocle look this cool before, and no one ever will again.