I’m a child of the 90s, but I’ve never really understood America’s fixation with Winona Ryder. My introduction to the dark queen of Gen X cinema was around 1999, when I was ten and my mom rented Mermaids on VHS. I was a sensitive almost-tween with a spunky little sister and early-onset existential angst, so I guess she thought it'd resonate, but I mostly found it boring.
A couple years later, I remember hearing people tsk tsk over Ryder’s 2001 arrest for shoplifting and drug possession, but I didn’t really understand what the big deal was. (To be honest, I still don’t. She got busted with pain meds and a few thousand dollars worth of couture. There are dude celebrities who’ve literally killed people and still have careers.)
Still, almost 20 years after “the incident,” it seems we’re in something of a “Winonassance.” You could point to latent 90s nostalgia, perpetuated by Seinfeld reruns and millennials who missed out on grunge and answering machines the first time around. Or Ryder’s star turn as a perpetually-distressed mother with a penchant for Christmas lights in Stranger Things.
At the end of the month she’s starring in the rom-com Destination Wedding with Keanu Reeves (who she might have married while filming Dracula in 1992), and two different indie movie theaters in New York City are hosting Winona-thons. With her entire oeuvre at my fingertips, I figured it was an apt moment to investigate the hype. So I hunkered down with my laptop and embarked on a Ryder binge that gives new meaning to “Winona Forever.”
I think I made a mistake starting my Winona-thon with this strange high school drama from 1986 starring a very young, very sexy (and often shirtless) Charlie Sheen. I was kind of turned on? But I also felt like I needed to be hosed down in one of those disinfecting rooms for people who handle toxic sludge?
Winona’s barely even in this one! She plays a 14-year-old band geek with an unrequited crush on the painfully dorky protagonist Lucas (Corey Haim). But he’s in love with the smart and beautiful new girl in town (Andy from The Goonies), and she’s got a hot thing going with the captain of the football team (adolescent Charlie Sheen). It’s so formulaic I could cry. By the end of the movie, I felt like I’d been tackled by a dozen linebackers (which is a real thing that happens to scrawny Lucas whilst trying to prove his manhood to his lady love).
Ryder Rating: 2/10, WE WANT WINONA.
How to Make an American Quilt (1995)
After slogging through Lucas, I threw chronology to the wind and decided to follow my whim-onas. (Sorry.) How to Make an American Quilt was on Netflix, so I tackled it next.
This movie reminded me of the Carrie-Aiden saga in Sex and the City, but with more quilting. Winona plays a flaky Californian named Finn who’s newly engaged to Dermot Mulroney—ubiquitous leading man of the 90s—and not super sure how she feels about it. Clearly the answer is to run away from your fiancé for the summer to live with your grandma and have a fling with a sexy farm worker. The good things: Winona getting old ladies stoned. Maya Angelou doling out relationship and quilting advice. And Jared Leto making a cameo as someone's baby daddy.
As a woman who only recently emerged from her own mid-20s identity crisis, I know how confusing it is to feel locked-and-loaded into a relationship you may or may not be stoked about. I really identified with Finn/Winona on that level. But I’m not sure what the message here is. Love is complicated, and sometimes people cheat, but it’s all part of the patchwork quilt of life?
Ryder Rating: 5/10, for using intimacy issues as an excuse to not complete her thesis on fertility rituals or some shit. Girl, your education is more important than some dude, OK?
The House of the Spirits (1993)
I mostly watched this movie because Meryl Streep plays a PSYCHIC. Otherwise this historical drama set in South America is a drag. Meryl's character is married to a horrible man who owns a hacienda and is also a rapist, and Winona plays their rebellious daughter who gets knocked up by a revolutionary played by Antonio Banderas. You know it's true love, because after there's a coup and the military is hunting for her man, Winona refuses to give him up, even when they throw her in jail and torture her. She's strong lady, which is cool. But I couldn't get over how unjust this movie is. Meryl dies, Winona gets beat up, but the evil dude never suffers for his sins? LAME.
Ryder Rating: 3/10, more magic and less toxic masculinity would've been nice.
The Crucible (1996)
We now come to the Daniel Day-Lewis portion of our program. He’s John Proctor, the cheating husband that playwright Arthur Miller (also a playboy) construes as a voice of reason during the Salem Witch Trials (representing the “witch hunt” of 1950s McCarthyism).
Winona plays Abigail Williams, the gal John Proctor had an affair with. She’s usually the villain of The Crucible, as the ringleader who convinced the good girls of Salem to dance naked in the woods casting love spells. When the town starts freaking out about witches, she’s the one whose lies result in some innocent women getting hanged. Abigail isn’t a sympathetic character. She’s pretty darn selfish. But the way Winona plays her, she’s the most interesting person in colonial Salem. Honestly, the real villain of The Crucible is the patriarchy.
Ryder Rating: 6/10, would’ve been better had the witches won...
The Age of Innocence (1993)
Sheesh, I was not about this other, earlier period piece starring Ryder opposite Daniel Day-Lewis. He’s playing the original fuckboy—an asshole lawyer named Newland Archer—who’s engaged to Winona’s character Mae Welland but not-so-secretly in love with Michelle Pfeiffer (who’s a badass bitch, by the way). But Newland can't talk about his feelings, even when Winona full-on calls him out on the fact that he’s infatuated with her cousin. I was furious.
Ryder got an Oscar nomination for this role, and she’s really good, toeing the line between frivolous socialite and calculating society lady who understands more than she lets on. But I wanted more of her in this film—or at least vengeance for her character. Instead I got Day-Lewis moping all over the screen like some lovesick man-puppy who doesn’t know what to do with all his privilege. I’ve never read the book, but I’m still mad the novel on which this movie is based was written by Edith Wharton, a woman.
Be right back, going to pen some fan-fic where Mae Welland takes a string of handsome and capable lovers and only sticks with Newland for the 19th century societal perks.
Ryder Rating: 4/10, I might as well have watched Phantom Thread again.
Watching Mermaids as an adult was so much better than watching it as a ten-year-old. The combination of Cher, Christina Ricci, and Winona is legendary, and there should honestly be more movies starring this trio. (Get at me, producers. I will write one.)
Ryder plays Charlotte, a Jewish teenager who wants to be a Catholic nun—essentially the opposite of her mom, played by Cher, who packs up her girls and moves cross-country every time she breaks up with a man.
There’s weird sex and gender stuff at play in this movie. Cher’s shoe salesman boyfriend, a total putz, has a line at one point to the tune of: “I’ve never wanted to hit a woman more than I do right now.” And Charlotte loses her virginity (after thinking she got pregnant from a very chaste kiss) on top of a nunnery bell tower while her five-year-old sister nearly drowns in a lake. It’s hard to imagine girlfriend has a super healthy sexual outlook after trauma like that… Still, Mermaids is a gem. I’m starting to understand the hype.
Ryder Rating: 7/10, because Winona is absolutely upstaged by Cher and itty bitty Christina Ricci.
Little Women (1994)
Oh man, Little Women had me wrecked. I watched it on a plane and sat there weeping in between two dudes somewhere over Colorado. Here’s a theme I’m noticing: Winona is in a lot of movies that point out how much it sucked to be a woman in olden days. There are so many conversations in Little Women about the things men are allowed to do that women aren’t. I kind of think Jo refused to marry Laurie (Christian Bale) because she was pissed he got to go to Harvard and she didn’t. Put that in your masculinity and smoke it, mister.
Jo is such a badass role for Winona, though. It’s been ages since I read Little Women, and I always thought of her as a tomboy. But I’m a petite, adult woman with a penchant for nearly getting in fights with rude men at bars. Also, I’m a writer. I may have a lot more in common with Jo (and maybe Winona?!?!) than I thought.
Ryder Rating: 8/10, I really wish Susan Sarandon was my badass single-ish mother during the Civil War. These ladies are tough as nails.
Girl, Interrupted (1999)
I was wary of Girl, Interrupted the way I was wary of The Bell Jar before reading it. I thought it would be super heavy, but holy shit it was relatable. I’ve never been hospitalized, but I have dealt with depression since I was a teenager, and even as discussions about mental illness have become more mainstream, there’s still this dumb stigma surrounding stories about “crazy women.”
Winona plays Susanna Kaysen, a real lady who was hospitalized for “borderline personality disorder” in the 60s, and the film is based on her memoirs. Most people think of Angelina Jolie in this movie (she won an Oscar for it). She’s incredible, but so is Winona, who’s just more subtle. Her iconic line at the end of the movie is horribly prophetic: “Have you ever confused a dream with life? Or stolen something when you have the cash? Have you ever been blue?”
When your mind is at war with itself, sometimes people do stupid shit. Who are we to judge? Less than two years after this film came out, Winona was arrested for shoplifting, and America vilified her. She filled the archetype of the spoiled Hollywood brat, who could probably afford everything in Saks yet chose to steal. I find this incredibly unfair. Susanna in Girl, Interrupted and real life Winona aren’t the same person. But I’m angry that people put Ryder on a pedestal, then condemned her without a hint of compassion.
Ryder Rating: 9/10, Winona in Girl, Interrupted is an American treasure.
Reality Bites (1994)
I’d never seen Reality Bites before embarking on Winona Fest 2018, but people fucking love this movie. I have to be honest, I had to watch it twice before I understood the allure. I do like the fact that Houston was a realistic place to pursue filmmaking in 1994… Nowadays, unless you make it big on YouTube, you’re condemned to eternal poverty in New York or LA, eating raw kale and defaulting on rent until you sell out and decide to work in advertising. Also Janeane Garofalo’s 90s platform shoe game is entirely on point throughout this movie.
I still think Ben Stiller and Ethan Hawke kind of suck as romantic prospects for my girl Winona in this movie, but that scene where she’s wearing a fluffy bathrobe and downing a Big Gulp is iconic.
Ryder Rating: 7/10, for being a 7-Eleven style legend.
I kind of half-assed this one, because it’s long and I had to watch it in college for an Intro to Fiction class, where we read a bunch of classic novels and also had to watch the movies they inspired. Mary Shelley’s Frankenstein was paired with the O.G. Blade Runner, for example.
Winona plays the reincarnated bride of Dracula, but she’s also married to Keanu (awkward), and one of the things I remember most about this film is the crazy neon green smoke that gets her all hot and bothered in her fancy castle bedroom.
While I was re-watching that scene, my roommate came home and asked why I was dressed like a goth madam in the middle of summer, but I have no idea what she was talking about...
Ryder Rating: 6/10, Winona deserves better than creepy, vampiric Gary Oldman.
Edward Scissorhands (1990)
I’d seen this movie before too, which is why I saved it nearly for last. But it’d been a while, and I was so charmed by the wacky simplicity of Tim Burton’s tale. I forgot what a contrast there is between Edward’s gothic existence and the perfect neon suburbia in the valley below his mansion. Honestly, I kept thinking about similarities between this movie and The Grinch.
But Winona’s role as Kim, the daughter of the Avon lady who takes Edward in, is so two dimensional. Sure, all the characters are caricatures. But I’m still mad Kim is so chill about Edward going back to his mansion and never seeing her again.
Ryder Rating: 7/10, for an incredible blonde wig but not much else. I'm feeling seriously tempted to dye my hair and get bangs now.
Somehow, I’d never seen this one. I remember seeing clips of Michael Keaton eating bugs as a kid, which turned me off from Beetlejuice for a long, long time. But I’m kind of amazed. Beetlejuice is a charming, classic film. Keaton is a disgusting louse (there are a lot of jokes about touching women without their consent, which feels weird and wrong in 2018, especially whilst the pussy grabber-in-chief occupies the White House). But other than that, Beetlejuice is awesome.
Winona is Lydia Deetz, whose entire ethos is summed up by this line: “My entire life is a darkroom. One. Big. Dark. Room.” She’s got ghosts as friends and is the O.G. (original goth). She was only 17 when Beetlejuice came out, but it defined her career. In 1989, Winona told Vogue "A lot of those clothes were my clothes. My skin was actually that pale." SAME, girl. After I watched this movie I felt compelled to hide from the sun and only wear black, because Lydia is an icon.
Ryder Rating: 9/10, being BFFs with ghosts is truly badass.
Wowee, Heathers is a trip to watch 30 years after its release. Winona plays Veronica, the popular girl with “morals,” which somehow justifies helping to murder other popular girls named Heather? I can’t believe Veronica goes along with J.D. long enough for his sadistic plans to reach a fever pitch, but the climactic scene, after her beau blows himself up wearing a suicide vest, is one of the craziest “I’m a survivor” moments in modern cinema.
Smoking my own cigarette after watching Heathers, I thought about how wild this movie must’ve seemed in 1988. And then it hit me, like a bomb: it’s kind of the perfect encapsulation of Winona. She’ll always be our beautiful outsider. Unlike the perfect blondes—Reese and Jennifer and Gwenyth—who succeeded her, Winona never needed us to love her. But now that’s she’s solidly middle-aged, perhaps we can forgive her flaws and embrace her for the perfectly imperfect woman she is, darker and more like us than we’d care to admit.
Ryder Rating: 10/10, I am Winona. Winona is all of us. Long live Winona. HOW VERY.
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