The 20 Best Cult Movies of the ’90s

It didn’t take much of a push for Vogue staff to revisit some of their favorite movies from the ’90s. After all, there’s nothing like a campy, indie, or otherwise offbeat classic to transport you to a simpler time. Here, a look at 20 cult ’90s films we could watch over and over again.

Drop Dead Gorgeous (1999)

Despite having no nostalgia for the viciousness of teenage girls, I could watch Drop Dead Gorgeous over and over. The plot centers around a small-town beauty pageant and the great, vile lengths people will go to win. With a stacked cast (including Allison Janney, Kirsten Dunst, Brittany Murphy, and Denise Richards) and incredible visual gags, it’ll make you laugh and gasp in equal measure. —Sarah Spellings, fashion news editor

Cruel Intentions (1999) 

This delicious film centers around two evil step-siblings—Kathryn (Sarah Michelle Gellar) and Sebastian (Ryan Phillippe)—who make a bet: Sebastian must deflower their prep-school headmaster’s daughter (Reese Witherspoon) before the start of term. There’s deception, heartbreak, revenge—plus, the evil Kathryn and her impeccable, ’90s minimalist wardrobe? To die for. —Christian Allaire, fashion and style writer

Jawbreaker (1999)

In my eyes, Jawbreaker is the O.G. Mean Girls. You’re missing out if you’ve never seen this campy, dark-humor classic: Basically, a trio of popular high school girls accidentally murders their best friend—the weapon is jawbreaker shoved down her throat—and then tries to cover it up. Along the way, they wear some seriously killer ’90s fashion. Watch it for this hallway-walk scene alone. —C.A.

10 Things I Hate About You (1999)

I’ve definitely watched 10 Things I Hate About You at least 10 times—okay, more like 100 times. It premiered in 1999, but I didn’t actually see it until a few years later when I was in junior high. My twin sister, best friend, and I became instantly obsessed; as soft-spoken and awkward preteens at a Catholic school in Indianapolis, we aspired to Kat’s sharp-tongued, no-fucks-given attitude—and, of course, we were truly in love with Heath Ledger. So much so that when he died a few years later, we wore head-to-toe black to school. —Emily Farra, senior fashion news writer

Cinderella (1997)

This movie has it all: incredible set and costume design, a soundtrack that is unmatched, and a wildly talented and diverse cast. For the first time in my life, I saw someone who looked like myself in a leading role on TV, and I was hooked. Eight-year-old me even begged my parents to let me skip a wedding ceremony once because ABC was showing a rerun; I eventually made it to the reception, but I wasn’t going to miss Whitney and Brandy performing “Impossible.” The film was recently added to Disney+, so I’ve had the chance to relive that fantasy again. But I am begging you, Disney, please add the soundtrack to streaming services! —David Vo, senior designer, digital

Billboard Dad (1998)

My favorite Mary-Kate and Ashley movie, ever. Love that two 11-year-olds were able to paint a perfect portrait of their dad on a billboard overnight. Also, their modern house off Sunset Boulevard. —Puja Prakash, senior manager, social media

Kuch Kuch Hota Hai (1998)

Growing up, I watched this movie as many times as I possibly could. It features three iconic Bollywood actors (Shah Rukh Khan, Kajol, and Rani Mukherjee) in a story line that romantic comedies nowadays could only dream of. Plus, the Western-Indian fusion of ’90s looks and the music videos are timeless. —P.P.

Fargo (1996)

I grew up in North Dakota, so I’ve got a special claim on this one—and if you have the chance to watch this with someone from the upper midwest, jump on it; there’re loads of inside jokes—but Fargo’s apotheosis of sheer, exuberant oddness amid a classic crime-caper-goes-wrong plot remains untouchable, fresh, transcendent, and, dare I say, necessary. If that’s not enough: It’s got Frances McDormand. The FX series has been a delight, but this is forever the godhead. (N.B.: The accent in this film isn’t by any stretch of the imagination from Fargo; it’s from Minnesota.) —Corey Seymour, senior editor

Pump Up the Volume (1990)

“Eat your cereal with a fork, and do your homework in the dark.” This is just one of the slacker koans uttered by Christian Slater, a.k.a. Happy Harry Hard-On, in the opening moments of this seminal movie from 1990. Nominally about a misfit high school kid stranded in an Arizona suburb who uses a pirate radio show to express his angst and stick it to the man, Pump Up the Volume is actually a deeply romantic, impeccably cool how-to for wannabe countercultural Gen X’ers—and a weirdly prescient parable about the rise of internet culture. The soundtrack—Pixies, Soundgarden, Sonic Youth, Bad Brains, Cowboy Junkies—is legend. Don’t get me started on Samantha Mathis. Also: Pump up the Volume is currently not available on streaming services. How punk rock is that? —Taylor Antrim, deputy editor

She’s All That (1999)

Without a doubt, one of the most iconic scenes in ’90s cinema belongs to Laney Boggs and her makeover debut in * She’s All That*. All this time later, I still find myself searching for that ruby red baby-doll ensemble (minus the stumble). With Sixpence None the Richer singing “Kiss Me” in the background, it was the first time I fell in love with a dress! “Kiss me, beneath the milky twilight / Lead me out on the moonlit floor / Lift your open hand...” —Lauren Sanchez, business manager

Metropolitan (1990)

I’ll never forget the scene when they hailed a taxi to the Hamptons. These were pre-Uber days, and I was then a nondriver living in the city and could totally relate to that. To me, it was a gesture as offhand as a glamour girl only keeping Champagne and maraschino cherries in the refrigerator. —Laird Borrelli-Persson, archive editor

The Virgin Suicides (1999)

I came to Sofia Coppola’s haunting Virgin Suicides for Josh Hartnett, only to realize his handsome presence was but a small part of why I fell in love with the film. The moody Air soundtrack, the loveliness of all five doomed sisters, the gossamer dresses throughout the ’70s-set flick. It’s a film that’s simultaneously hard to watch and wonderful to behold. —Lilah Ramzi, commerce editor

Singles (1992)

Singles! How is this not already on this list?! Not only have I seen this movie a million times in the almost 30 years since it came out (dear God), I also owned the soundtrack—on cassette!—the tracklist of which I can still recite. Every time I think about Bridget Fonda’s wardrobe or the way the film captures Seattle’s era-specific coffee-shop culture, all I hear is the intro to Paul Westerberg’s “Dyslexic Heart.” Na na na na na na na na na na na na na na na. —Celia Ellenberg, beauty director

Romy and Michele’s High School Reunion (1997)

No matter how hard I try, I can’t resist the charm of the wacky fashion in Romy and Michele’s High School Reunion. The gaudy plastic earrings, the teetering platforms, the sexy businesswoman ensembles, and those unforgettable metallic and marabou-trimmed dance dresses—what’s not to love? Not to be forgotten, either, is Justin Theroux as an all-black-wearing, cigarette-smoking bad boy. —Steff Yotka, fashion news and emerging platforms editor

Trainspotting (1996)

Trainspotting is a headache of a film, and I cannot watch it more than once every couple of years. It makes me want to immediately take a shower. This is Ewan McGregor’s career-best performance, though—other than that one great episode of ER. —Sache Taylor, executive assistant to the editor in chief

Welcome to the Dollhouse (1995)

Oh, the wretchedness of seventh grade, the horrors of suburbia. —Lynn Yaeger, contributing editor

The Pillow Book (1996)

One of my best ’90s moments involved my local library getting a copy of Peter Greenaway’s The Pillow Book (1996), which I rented and watched in my parent’s living room with all my school friends. I felt incredibly sophisticated and very grown-up until my parents returned home and grounded me for the next month. —Janelle Okwodu, senior fashion news writer

The Search for Signs of Intelligent Life in the Universe (1991)

It’s gospel by now that Lily Tomlin is a star; but more than being a very talented film and television actor, she was once a sensational presence onstage—the most obvious, most persuasive proof being in her Tony-winning solo show, The Search for Signs of Intelligent Life in the Universe. Luckily for those of us who missed its Broadway run in the 1980s, The Search for Signs was made into a movie in 1991, and every one of Tomlin’s hilarious personas (Trudy, Agnes Angst, Tina, Brandy, and others) all but flies off screen. —Marley Marius, associate features editor

Before Sunrise (1995)

Ethan Hawke once jokingly described Richard Linklater’s Before Sunrise, Before Sunset (2004), and Before Midnight (2013) as “the lowest-grossing trilogy in the history of motion pictures,” and while that may well be true, it’s also one of the most swooningly romantic. You (probably) know how the first one goes: boy (Hawke) meets girl (Julie Delpy) on a train, boy convinces girl to walk around Vienna with him, boy and girl talk about life and death and love and magic until they part, promising to one day meet again. (Spoiler: They do, but not quite as planned.) —M.M.

A Tale of Autumn (1998)

If I were pressed to (very reductively) describe the mid-to-late-career films of Éric Rohmer, I’d say that they were very talky and very sexy, often centered on beautiful young people philosophizing on the beach or over a simple dinner or in some wildly overgrown provincial garden. A new favorite of mine from that period is 1998’s A Tale of Autumn, starring Béatrice Romand as a windowed vintner being nudged back into the dating game by her best friend (Marie Rivière) and her son’s girlfriend (Alexia Portal). It’s a gentle comedy of manners, a meditation on (re-)opening oneself up to love, and a very effective—if accidental—advertisement for abandoning your life in the city to live on a vineyard in France. In other words, it’s a perfect movie. —M.M.

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