This list was born out of a conversation about Troy Dyer. Namely, a conversation wherein the question who’s Troy Dyer? was visited upon by one of our otherwise enormously cultured, whip-smart 20-something editors. Having come of age under the waifish ingenue wing of Winona Ryder, it had never occurred to me there would one day exist a generation who knew nothing of the man who answered the telephone, “Hello, you’ve reached the winter of our discontent.” After a brief poll around the Clique offices, a list of must-watch films began to compile for our young guns. Most possessed a cursory knowledge of teachable ’90s moments, but I insisted on offering a master class. Keep scrolling to discover which of the top ’90s movies you need to add to your queue.
Shot in Texas, Reality Bites follows a set of Generation X friends as they navigate life post-graduation. Written by Helen Childress and masterfully directed by Ben Stiller, it’s a coming-of-age saga of burnout angst, romantic drama, and pointed social commentary. Winona Ryder, outfitted only in the most quintessential of ’90s garb, stars as Lelaina Pierce, a driven, promising, and naive valedictorian navigating her way through the beginnings of her career. Ethan Hawke, as Troy Dyer, is the underachieving best friend who may (or may not) be in love with her. Dyer is the ultimate bad boy with a heart of gold. Lelaina remains the reigning queen of frustrated ambition and post-adolescent malaise. Watching her navigate dating a yuppie businessman with his act together (played by Stiller) while falling heedlessly in love with her laid-back bestie is everything. You’ll never look at a $5 coffee date the same way again.
Lelaina: “I was really going to be somebody by the time I was 23.”
Troy: “Honey, all you have to be by the time you’re 23 is yourself.”
Every young professional needs to know how to order a “Businesswoman’s Special.” The heartfelt adventure of two best friends on a quest to impress the mean girl–addled student body at their 10-year high school reunion is funny and adorable. Watch it on your next girls’ night.
Romy: “I’ve been killing myself for eight days, and I gained a pound.”
Michele: “That’s impossible. Did you deduct 16 pounds for your shoes?”
Millennials may or may not recall the record store blues that ran rampant throughout the 1990s. Nowadays, only the niche has survived, with chains shuttering their businesses in favor of the digital revolution. Circa 1995, “Damn the Man. Save the Empire” was something of a mantra. The plot of Empire Records follows a group of friends working at a record store as they learn it is being sold. Liv Tyler’s classic ensemble, featuring Dr. Martens, an angora sweater, and a miniskirt, is up there with Alicia Silverstone’s Clueless plaid-on-plaid look in terms of sartorial icon status. Happy Rex Manning day to you all.
A.J.: “Lucas, do you think it’s possible for a person to be in love with someone else and not even know it?”
Lucas: “In this life, there are nothing but possibilities.”
When this movie hit theaters, one of the most popular pop songs on the radio contained the lyric “so you’re Brad Pitt—that don’t impress me much.” As such, Meet Joe Black occurred in the wake of a debate as to whether or not Brad Pitt was the coolest ever, or if he was merely a pretty face and a set of abs. Those of us who watched him speak Patois and convincingly taste peanut butter for the first time (both scenes in this remarkable film) would passionately advocate on behalf of his finely attuned, deeply nuanced chops. But this was post-Seven, pre–Tyler Durden; it was a confused time. Technically the plot is about a media tycoon at the end of his life and his bizarre encounter with the grim reaper. To avoid spoilers, I will say the inciting incident of the film occurs when Claire Forlani’s character meets the perfect guy in a coffee shop (obviously, Pitt), and something happens to him. After this movie came out, “I’m still in love with the guy I met in the coffee shop” emerged as the clearest way of expressing one’s paramour had digressed into something confusing or less desirable than the guy who swept you off your feet upon your first meet cute. It holds up.
Joe: “I don’t care, Bill. I love her.”
William: “How perfect for you, to take whatever you want because it pleases you. That’s not love.”
Joe: “Then what is it?”
William: “Some aimless infatuation, which, for the moment, you feel like indulging; it’s missing everything that matters.”
Joe: “Which is what?”
William: “Trust, responsibility, taking the weight for your choices and feelings, and spending the rest of your life living up to them. And above all, not hurting the object of your love.”
The film that cemented the pixie cut as the lone indicator of an alternative lifestyle, Sliding Doors will make you firmly rethink every subway car you’ve ever missed. Set in London, the film features Paltrow’s Helen as a woman fired from her job at a PR company. Returning home after work, her life splits off into two factions: one in which she misses the train home, and another in which she arrives home early to find her boyfriend, Gerry, cheating on her. At its core, it is a story of hope, resilience, and the boundless possibilities that await the bravery of chopping off one’s hair and holding out for a dude who properly appreciates Monty Python.
Lydia: “Gerry, I’m a woman. We don’t say what we want, but we reserve the right to get pissed off if we don’t get it. That’s what makes us so fascinating. And not a little bit scary.”
Isaac Mizrahi’s fashion documentary is up there with Diana Vreeland: The Eye Has to Travel as one of my personal favorites of all time. It is the ultimate flick on a blustery day. Prepare yourself for a parade of supermodels, from a baby-faced Amber Valletta to all the marquee names of the day: Naomi Campbell, Kate Moss, Linda Evangelista… the gang’s all here. The collection is a cross-pollination of Nanook of the North meets Mary Tyler Moore. There exists a pivotal scene in which peerless goddess Eartha Kitt croons her way through her NYC pad drowning in a sea of pet poodles. Yes, all this is waiting for you.
Isaac: “Naomi, I have to tell you about this thing in the show. Some of the girls, maybe you even, are going to be changing on stage where people can see you sort of, but you’ll be in a bra and panties the whole time.”
Kate: “What? No.”
This film scared the Prada backpacks off any American girls with dreams of galavanting through Thailand footloose and fancy-free post-graduation. That kooky friend who’s sort of a loose cannon, but gee, she sure knows how to liven things up? The one your mom constantly worried about on school trips? Brokedown Palace taught us how that friend wielded the ability to blithely land you in a Thai prison for drug trafficking, all simply by flirting with Australians. The story of two best friends on the worst-case-scenario vacation of all time is heartbreaking and harrowing. Claire Danes rules.
The entire film.
Alice Marano: “That’s all freedom is: an illusion.”
Cameron Crowe’s romantic romp about a group of 20-somethings living in the same apartment complex in grunge-era Seattle, Singles gives us Bridget Fonda and Matt Dillon in all the flannel you can handle. Centering around the music scene, the film features the sort of soundtrack one could only hope to expect from Crowe. It’s a bit like Melrose Place, with better dialogue and wall-to-wall Pearl Jam, Soundgarden, and Alice in Chains.
Janet Livermore: “Somewhere around 25, bizarre becomes immature.”
Winona Ryder’s diverse body of work has much to teach us all. As Finn, a young graduate student finishing her master’s thesis and experiencing doubts regarding her pending nuptials to Dermot Mulroney (in itself baffling), she learns of love, heartache, and sacrifice at the hand of her grandmother’s quilting bee. It is a film that explores generations of women through tumultuous relationships and age-old friendships. Weaving together multiple storylines, the plot itself is a rich emotional tapestry of revelations and colorful meditations on the trials and tribulations of growing up.
Finn: “Young lovers seek perfection. Old lovers learn the art of sewing shreds together and of seeing beauty in a multiplicity of patches.”
The first installment of Richard Linklater’s film trilogy, Before Sunrise follows an American tourist (Ethan Hawke) and a spirited French girl (Julie Delpy) as they spend a single day together in Vienna talking about everything under the sun, from poetry to parents to love’s unmitigated confusion. Back in the day, Before Sunrise was an isolated incident. Today, first-time viewers are bestowed with the time-warping ability to watch the relationship move forward, backward, and sideways over the course of two decades. Young audiences will miss out on the whole aging-alongside-the-characters thing, which admittedly informs the viewing. This first film remains my favorite of the three. A stand-alone piece of masterful filmmaking, it is chock-full of intimate, surprising performances and inspired dialogue.
Celine: “If there’s any kind of magic in this world, it must be in the attempt of understanding someone, sharing something. I know it’s almost impossible to succeed—but who cares, really? The answer must be in the attempt.”