Winona Ryder Is A Queer Icon: 90s Romcoms Ranked By Lesbianism

It is a universal truth that every ’90s film breakdown must include Winona Ryder.

The ’90s were the Golden Era of romcoms, obviously.  Many of our favorite movies from this decade don’t seem THAT queer—to the naked eye, anyway. But it’s time to always look on the gay side and find the queer lining in ’90s romcoms. Put on your coziest flannel and take a deep dive into all that’s blatant, implied, or just plain wishful thinking (and probably fanfiction somewhere!) in this list of 10 ’90s romcoms ranked from the least queer to the absolute QUEEREST.

Sleepless in Seattle (1993)

Obsessive stalking is not okay, even if you’re Meg Ryan! This classic may not have aged too well in terms of chasing down someone you’ve only heard on the radio, but the jazzy soundtrack is stellar, Nora Ephron’s dialogue is on point, and really, who didn’t want to be Meg Ryan in the ’90s? Rosie O’Donnell wasn’t out of the closet yet when she played Becky, the trademark Loyal Best Friend. But we like to think that Becky was getting her kicks at queer bars while fielding cray-cray phone calls from Ryan’s Annie Reed. And who knows, maybe Becky found a loyal wife in the process.

My Best Friend’s Wedding (1997)

This would be a way better movie if sabotaging, straight mean girl Julianne (Julia Roberts) was trying to score with blushing bride Kimmie (Cameron Diaz) instead of the dull groom, Michael (Dermot Mulroney), her childhood friend. Kimmie is an adorable femme dream, from her sweet little frocks to her penchant for awkward karaoke to her genuine kindness to Julianne. She’s definitely the girl who makes out with other girls at keg parties and secretly loves every lip nip and tongue tangle. Team Kimmie!

American Pie (1999)

True, this bro-y 80’s-esque let’s-lose-our-virginity romp is rife with toxic masculinity, but stay with me here. American Pie makes this list because of one singular, and very hot, scene. Buxom exchange student Nadia (Shannon Elizabeth) getting down with herself to lady mags is a huuuuuuge indication that her slammin’ body is worthy of better than wannabe Jim (Jason Biggs). Nadia’s knowledge of exactly what turns her on (ahem, titties) could bring out the bicurious in the straightest of girls. (Mena Suvari’s choir girl Heather, perhaps?)

Clueless (1995)

The gayest? Maybe not, but the still-quotable and ’90s-tastic movie makes the list on femme style alone. Let’s talk lez fashion. Tai’s pre-makeover skater chic translates pretty well to 2019 stoner dyke… maybe just nix the mom jeans. (Also, RIP Brittany Murphy, we love you.) And lovably meddling Cher’s style is high femme at its peak 90’s cuteness. The plaid pleated miniskirts and matching jackets! The Calvin Klein slipdresses!  The knee socks and platform heels and Alicia Silverstone’s fetching little white boa in the poster! And the lesbian AF gym teacher! There’s so much girl-on-girl tension in the “suck and blow” game, this movie is a lesbian dream if you squint. Not to mention its signature catchphrase “as if!” was inspired by Amy Heckerling’s own gay posse.

The Truth About Cats and Dogs (1996)

Can we just have a reboot where Janeane Garofalo’s Abby and Uma Thurman’s Noelle end up together? They’re such a perfect couple: sarcastic and sweet, overeducated and… model, baggy jeans and floral spaghetti straps—you get the idea. Noelle is the glamorous purebred kitty cat who’s intimidating until you hear her squeaky meows and rumbly purrs; Abby is the bulldog with really soft fur whose bark is way worse than her bite. No actual kiss in the movie? No problem, we’ll use our imaginations.

Reality Bites (1994)

It is a universal truth that every ’90s film breakdown must include Winona Ryder. Eight years before she was busted shoplifting (we all make mistakes, babe), Ryder shined in Reality Bites, where her overachieving character Lelaina adorably stumbled through post-college life with her best friends by her side. Sex talk reigned supreme, especially among Lelaina’s pals Sammy (Steve Zahn) and Vickie (Janeane Garofalo), the latter of whom kept a diligent list of everyone she slept with between shifts at the Gap. Not a lot of true-blue lesbian content here, but Ryder’s big brown eyes and copious angst could turn even the straightest girl a little bit bi.

Now and Then (1995)

Big Dyke Energy, aka the lesbian equivalent of Big Dick Energy: Roberta, played by Rosie O’Donnell (Now) and Christina Ricci (Then), has it in spades. The tough girl of her adolescent posse, she says bad words, kicks boys’ asses at baseball, and tapes down her boobs. She’s the chick who did have her first kiss with a guy but threatened to beat him up afterward. (No fantasy, this really happens in the movie!) Roberta has rainbows coming out of her ears and a lot of Pride Parades in her adult future… not to mention she’s the one you really want leading weekend softball teams. Batter up!

10 Things I Hate About You (1999)

Please, there’s no way Kat Stratford (Julia Stiles) doesn’t like girls. Maybe she doesn’t know it yet, but the second our riot grrl jets off to her dream school, Sarah Lawrence College, she’s going to experience her first lady kiss within 24 hours. And Patrick (Heath Ledger) seems like he’d be cool with polyamory. Kat’s outspoken feminism, love for Bikini Kill, and resistance to patriarchal norms like her own senior prom are still #goals for the modern queer gal. These days, she’s probably organizing #MeToo events and campaigning for LGBTQIA politicians by day and penning female-female erotica by night. Rock on, Kat!

The Incredibly True Adventure of Two Girls in Love (1995)

I mean, I could just say “starring pre-L Word Laurel Holloman, star of my sex dreams” and leave it at that. But instead, I’ll imagine her teen character Randy Dean, a short-haired working class cutie, living out her first true love with Evie, the rich girl from the right side of the tracks. Then one day, Randy, tired of pumping gas and dealing with small-town prejudice, buys a plane ticket to Los Angeles, where she crosses paths with a well-to-do gallerist, grows her hair long, dyes it blonde, and makes up a white lie that said well-to-do gallerist is her “first, last, and only.” We see you, Tina!

All Over Me (1997)

I can’t do a ’90s romcom rundown ranked by lesbianism without Leisha Hailey. I don’t want my bi card revoked. Adorable, charming and so, so gay, Hailey’s character Lucy rocks rainbow socks, Docs, and bright pink hair while seducing baby dyke Claude (Alison Folland)… and all of us, really. Most of us will sleep with a pink-haired beauty at some point in our lady-loving lives—and if she looks like Hailey, so much the better. No wonder k.d. lang always looked so smitten on the red carpet.

But I’m a Cheerleader (1999)

This grand marshal of ’90s lesbian romcoms is basically a girl-on-girl fairy tale. Pink as far as the eye can see, a RuPaul cameo way before Her Highness got problematic, a studly love interest… you get the idea. And princess Megan is a cheerleader. So much fantasy in only three syllables. Also darling pleated skirts, a can-do spirit, and the ability to find The One in the most dangerous of places: a conversion camp! Megan’s a Disney heroine with a sex drive and so many secrets behind those doe eyes. We want to live happily ever after with her.


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