8 Winona Ryder Movies That Tug On Our Nostalgic Heartstrings

by Riese & Laneia

Sometimes we just sort of start thinking about Winona Ryder, and then we start talking about Winona Ryder, and then we want to write entire posts about Winona Ryder and how she was in all of these movies that meant so much to us when we were kiddos and teenagers. So then we do that. And then we post it. AND NOW HERE WE ARE.


 

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Lydia Deetz, Beetlejuice (1988)

Laneia: Beetlejuice was a seriously scary movie and it freaked me out COMPLETELY, but there was Lydia, and she wasn’t scared of anything. Her parents let her wear weird shit and be in a bad mood, which was really appealing as a nine or ten year old. I think this is what happens when you’re an only child — you make up your own big sisters as needed. I must have really needed someone who was sullen and dark, because Beetlejuice kicked off my imaginary kinship with Winona Ryder.


 

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Veronica, Heathers (1988)

Veronica Sawyer: I just killed my best friend.
J.D.: And your worst enemy.
Veronica Sawyer: Same difference.

Riese: These teenage girls are angular peacocks, they are not afraid to take up space. They wear bright blazers with boxy shoulders and bold broaches, hair that crests above the forehead or comes together around a scrunchie in a knot of yellow curls. The Heathers are mean and they teach Veronica to be mean, too, but Veronica really only wanted to be cool, but then she finds out that being cool = being mean. Then a darkly smiling sociopath asks her for a game of croquet but means “sex in the grass.” The only way Veronica can be free of that bitch Heather is to out-bitch Heather, like with violence and murder.

I’ve always held the original script of Heathers among the great literature that I’ve ever read,” said Winona Ryder about Heathers. “For me, it’s like, Ezra Pound, Philip Roth, Saul Bellow, and Daniel Waters, you know?” Winona’s agents didn’t want her to take the role but Winona got down on her knees and begged. It’s her favorite movie, she almost has it memorized.

Producer Denise Di Novi said, “Winona was so smart. She was fifteen, she turned sixteen on the movie. She was a prodigy. From a very young age, she was an old soul. She really got the words and the imagery. She had watched tons of old movies. She was really sophisticated intellectually. She had the beauty of Veronica. She had the intelligence. She was just the perfect anti-Heather.”


 

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Kim, Edward Scissorhands (1990)

Obviously this film had a lot of lesbian subtext because Johnny Depp, who was basically a lesbian for most of the ’90s, had hands made out of scissors. This is a combination of two lesbian situations: scissoring and fingerbanging. Also, Winona Ryder.


 

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Charlotte Flax, Mermaids (1990)

Laneia: Charlotte wanted to have sex and I related to this a lot. She needed intimacy but she was terrified of it, and she was clumsy and weird. All of these things were my things, too, even though I didn’t know it then. I was mostly just obsessed with her face and her boots, and Mrs. Flax’s dedication to finger foods as meals. This was another movie when Winona was my big sister and I didn’t realize it.


 

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Lelaina Pierce, Reality Bites (1994)

Lelaina Pierce: I was really going to be somebody by the time I was 23.
Troy Dyer: Honey, all you have to be by the time you’re 23 is yourself.
Lelaina Pierce: I don’t know who that is anymore.
Troy Dyer: I do. And we all love her. I love her. She breaks my heart again and again, but I love her.

Riese: I saw this movie in 1994 and I pretended like I liked it but I didn’t really understand it, not until much later. Look at this girl! She’s smart and pretty and ambitious but being a grown-up is hard, right? Yes, you feel this. You relate to this. I saw this again in my twenties and knew like a psychic on the telephone that this was my jam.

This is one of many mid-90s films (and Broadway musicals) that are preoccupied by what it means to “sell out” as an artist, which seems like such an indulgent concern these days. Like that you’d even have the option, really, I think at this point we’re just looking to be sold, period, or bought, whatever.

Again Winona Ryder walks the line between charming and insufferable, but if you can relate to Lelaina you probably won’t notice the selfish parts.  Troy seemed really sexy back then but now I just want to push him off the roof.

Laneia: Reality Bites became the framework for my understanding of the world and my aspirations. This time I knew that Lelaina was the big sister I desperately needed, and I decided upon first viewing that her life was everything I wanted. I wanted cute dresses and potential I could squander, a super weird friend who slept around, at least one very affected and greasy boy person to makeout with, a short haircut, and the space in which to indulge in a complete and total emotional breakdown. I wanted to know the lyrics to old songs and sing them loudly in strange places, I wanted a boxy German car I could take for granted, I wanted a video camera. I memorized the lines like I’d be quizzed on them later. I braided my bangs down the front of my forehead and waited patiently to understand what the fuck everyone in this movie was so upset about.

Winona just manages to make every horrible selfish thing seem like the most appealing bay window to sit in for days. I think she does it in every film!


 

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Jo March, Little Women (1994)

Riese: Jo March and Winona Ryder already occupied the same bit of my brain, so when she was cast as Jo I thought to myself, of course. She’s the charming, ruddy tomboy, the captain of the ship, intellectual and affectionate, even with hair to her waist (until she sells it, of course) and skirts to the floor. She’s too busy for boys (until she isn’t, but we’re used to that, I guess) and too ambitious for the kind of womanhood practiced in homes less progressive than her own. Yes, the world is full of darkness and war, poverty and illness and death, but there is also Christmas, and music, there are piles of sisters and kittens, there are costumes and flowers and big old houses with hearths. I loved her dearly at this time, and I loved Claire Danes dearly too, and Kristen Dunst, to a degree, and even Samantha Mathis, and definitely Christian Bale. I loved The Alcott House, where I took writing classes with instructors wearing period costumes pretending to be the March sisters. In this movie Winona Ryder played me, had I been born way back then instead of just now.

Laneia: Little Women was one of the last movies I watched with my mom before launching into full-fledged horribly selfish teenager mode, and we cried and CRIED and cried some more. Having Claire Danes in this one was like a miracle! This whole cast was amazing, actually. Marmee is home INDEED.

 


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Finn, How To Make An American Quilt (1995)

Laneia: How to Make an American Quilt was DELICIOUS and entirely underrated. This is a Winona Ryder feelings post, so in the interest of staying on topic I’ll say that I thought Finn Dodd was annoying and wretched and I hated her. I was 100% more interested in the backstory of the older women — Samantha Mathis and Claire Danes were the real reasons I was there — and then Maya Angelou, Anne Bancroft, Alfre Woodard?! I just wanted to hang out with these old ladies and talk about their lives forever.

Riese: I barely remember this movie besides that it was sold out at Showcase Cinemas so we had to buy tickets to something else and sneak in and sit on the floor and we missed the beginning. I just couldn’t believe how lucky we all were that Winona Ryder and Claire Danes were in the same movie AGAIN.


 

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Susanna, Girl, Interrupted (1999)

Riese: Susana is a stubborn and unhappy adolescent girl born at the wrong time in the wrong place to the wrong people. When I first saw it I thought, “I wonder if I would’ve been sent away back then,” you know? But I was young and foolish, probably, even though this movie is kind of about how being young and foolish and female can look like insanity to everybody else. When I remember this movie I remember Angelina Jolie at the ice cream shop, firstly. Then I remember Susana’s journal being read aloud in the dark tunnels below the institution, I remember her silent in a car not knowing where she’s going, or lighting a cigarette in somebody’s office with all the windows closed. She’s just so aggressively herself, full of questions, sick of everybody imposing their values on her body and she’s been fucked over by so many alleged grown-ups that it takes time to realize some of them want to help her.

She’s small, sure, physically, but she can do big things (“you chased a bottle of asprin with a bottle of vodka”) or she can splash in the tub, she can yell and challenge labels and feminine norms or she can unleash a torrent of ugly bigotry, she can blow smoke everywhere and make big gestures in oversized shirts. This is a movie about a girl yanked out of the world of men — men who in their maleness can’t penetrate her facade — and placed into a world of girls — girls who split her open because they could see her. So she learned empathy, or something like it. Right?

Laneia: I’d already read Girl, Interrupted (pretty sure it was an Oprah pick) because doing so seemed to fall in line perfectly with my Lelaina-like ambitions, so I was super excited when Winona was cast as Susanne. Even though it’s widely held that Angelina upstaged her in this film, I still think she did the role justice. Now I can’t think about Girl, Interrupted without getting depressed about Brittany Murphy, so.

Riese: I read the book after I saw the movie, and sometimes I wonder what Lisa would’ve looked like if she wasn’t already Angelina Jolie in my mind. And by that I mean if she wasn’t already my dark dangerous girlfriend who knew how to break rules and told it like it was. I mean, she was bad news. But I was 18.


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Riese is the 36-year-old CEO, CFO and Editor-in-Chief of Autostraddle.com as well as an award-winning writer, blogger, fictionist, copywriter, video-maker, low-key power lesbian and aspiring cyber-performance artist who grew up in Michigan, lost her mind in New York and then headed West. Her work has appeared in nine books including "The Bigger the Better The Tighter The Sweater: 21 Funny Women on Beauty, Body Image & Other Hazards Of Being Female," magazines including Marie Claire and Curve, and all over the web including Nylon, Queerty, Nerve, Bitch, Emily Books and Jezebel. She had a very popular personal blog once upon a time, and then she recapped The L Word, and then she had the idea to make this place, and now here we all are! In 2016, she was nominated for a GLAAD Award for Outstanding Digital Journalism. Follow her on twitter and instagram.

Riese has written 2581 articles for us.

28 Comments

  1. When I confess that I was so looking forward to essentially becoming a version of lelaina when I reached my twenties people always think that’s weird. I must have just had a sixth sense I was going to be disenchanted with the world, be pretty self involved, and really enjoy a big gulp when I finished college. I’m glad I have some kindred spirits somewhere in the world.

  2. hearing the music from how to make an american quilt makes me cry pretty much instantly. same with the music from little women. thomas newman oboe solos + winona is apparently just way too much for my delicate emotional constitution to handle. I remember taking both of those movies (on vhs) with me to college like security blankets. i was so little and scared and pathetic! but I knew I had to be brave like dying beth and her quivering chin. i would have had to include lucas on this list as well even tho her part was relatively small. that might be the winona role i relate to the most tbh. always wanted to be lelaina but was/am forever a rina

  3. seriously. I rewatched girl interrupted a couple years ago and thought it was overly melodramatic compared to when I loved it when I was 13, but your interpretation, Riese, is very interesting! time for another rewatch I think.

  4. Ahh, thanks for this! I had completely forgotten about Reality Bites, although it was such a Thing for me at 14! And Jo, oh wonderful, inspiring gorgeous Jo! Wish she was here and we could discuss Dickens and the pains and joys of independence and creativity. Or something like that.

  5. “Obviously this film had a lot of lesbian subtext BECAUSE JOHNNY DEPP, WHO WAS BASICALLY A LESBIAN FOR MOST OF THE ’90S, had hands made out of scissors.” This made me laugh out loud so hard I may have woken up my roommate and I don’t even know why.

  6. I think I was just too young to find most of these at the time, but it’s really something to see all that she did. For some reason her shoplifting episode stuck in my mind. Edward scissorhands was masterful and girl, interrupted will always be pulling at my heartstrings! I watched Ryder kiss Jolie over and over. And then years later when I had a bad injury that put me out of commission, and as an introvert, the fantastic concept just stayed with me.

  7. So many feelings. Looking back on it, Winona Rider in Heathers may be my root. She’s certainly one of those women I didn’t know if I wanted to be her or be with her.

    I saw Reality Bites when it came out in ’94, when I was 24, and I pretty much HATED Lelaina. The whole movie hit way too close to home, but I was so annoyed with Lelaina. She had a real job, a freaking real job, and she QUIT in a snit. And she conned her parents to get more money. Meanwhile, I’m practically killing myself working a shitty retail job so I can be independent. And reading all these stupid newspaper stories about what useless slackers Gen Xers are. And this stupid movie just perpetuated that stereotype. (I may have a few unprocessed feelings from that time in my life).

    /end rant

    • yup, same here, for everything. I resented that Winona in Reality Bites had a job that she quit, but, moreover, that she had a boyfriend. That annoyed me, so I didn’t enjoy the movie. All that promise as Jo March squandered on Ethan Hawke. The decisions of youth etc.

      • “All that promise as Jo March squandered on Ethan Hawke.”

        Hah. That made me laugh. I feel like all of Ethan Hawke’s movie love interests are squandered on him – Uma Thurman, Julie Delpy, Winona, they all could do so much better. I just don’t get his appeal.

  8. There is a movie called, “Welcome Home Roxy Carmichael” that I highly recommend. When I was a young teen I bought a VHS copy of it at a video store sale. I bought it because my gaydar has always been tight, I just knew it had a gay theme. Google has confirmed that YES it is on youtube. It will make all of your lesbian + WR dreams come true. Melissa Etheridge is on the soundtrack OK

    • Yes! OMG! Yes! Personal story – so it’s truly fucking baffling to me that I didn’t figure out the whole gay thing until like, way, way beyond when it it would have been reasonable to figure out. Case in point – in middle school, I had this obsession with Winona Ryder. I rented all of her movies, even her most obscure ones. Lord only knows what my poor friends must have thought of me because all I would want to watch at sleepovers was Fried Green Tomatoes and Winona Ryder films. In any case, I remember that I had seen almost all of her repertoire, except for Welcome Home Roxy Carmichael, so I had my mom take me to the video store (remember those!) to see if they had it. I looked and looked, but didn’t see it. While I was looking, a gaggle of popular girls wandered into the store. I, being the middle school equivalent of Mean Girl’s Janis Ian, feathered up my pride and avoided them with disdain. However, not finding what I was looking for, my mother prompted me to ask the store clerk. One of the girls – one of the cuter, sportier girls who I kind of didn’t disdain and in fact secretly kind of liked – overheard me. Somehow she immediately found the tape and brought it to me, which mortified me in ways I couldn’t explain at the time. Of course my mortification at this cute girl aiding and abetting in my not-so-secret Winona Ryder obsession has seared itself into my brain, so I have an usually strong memory of this movie. I later did the same googling, and the fact that it originally had a lesbian plot line just makes everything so much more perfect. I’m really happy that someone else remembers this movie! It really is her gayest.

  9. Thank you, this article is completely relevant to my interests. I will now go back and watch Edward Scissorhands through the queer lens, which I suspect will be magical (and which is probably why I have always unwittingly loved it so much in the first place).

  10. Mermaids was definitely one of the best things to come out of the ’90s. I watched it over and over again and I think secretly wanted to be just like Charlotte Flax.

    Also can we talk about Bram Stokers Dracula? And how all vampire films are just a little bit gay.

    Reality Bites spawned a brief late-nineties obsession with Jeaneane Garafalo (because I think we can all agree that Vickie was so much cooler than Lelaina). I watched this dumb movie with her and Uma Thurman called “The Truth About Cats and Dogs” so many times and I’m not even sure why. I probably wanted them to make out.

    Oh, Winona Ryder was also in this movie called Boys in 1996 (according to Wikipedia) that I watched a lot. Some of it was filmed near where my parents live and it was also about a boarding school, which I enjoyed.

  11. I was OBSESSED with Little Women. My very first movie crush was on Laurie — I so wanted to be Jo, and I couldn’t believe she turned him down.

    That was how I identified with my girl crushes back when I was eleven and twelve — I assigned my longing to wanting to BE the amazing girl. Since I wanted to BE Jo, I crushed on Laurie.

    And honestly, even today, the hottest girls are still the ones I’d kind of like to be. 😉 How does that Daphne Gottlieb poem go? “It’s on, but I don’t know if I want to be her, fuck her, or borrow her clothes.”

  12. I really, really, hate Reality Bites. I would loathe to be like Lelaina in my late twenties- a crappy employee, self-obsessed, going after jerks, and stealing money from my parents. I almost hate it as much as I hate Rent.

  13. For me Girl, Interrupted was kind of… easy for me to lean on as a teenager? I got pretty into it after my first stint in the psych ward after a suicide attempt, so you can guess why this movie was appealing.
    I found out two years later than I’m also borderline, like Susanna. And I really like how she challenged the whole “sexual promiscuity” part of the “self-damaging” diagnostic criteria. Like, who decides if it’s healthy or unhealthy? Why should someone with no idea about those experiences get to decide that?
    Anyway.
    I think it’s really funny that I identified so much with Susanna, and turned out to have BPD like her.

  14. We just had a three-generation weep-fest while watching Little Women (at the moment when Beth comes downstairs and is presented with the new piano – you know that moment). Kid and I both totally fell apart. Grandma teared up, but pretty quickly switched to giggling at us. Which is to say, how is it that I hadn’t watched this movie before?

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