The 15 Best Gen X Movies of All Time

Generations are defined by many things: their fashion sense, their colloquial slang, their politics, whether they attended Woodstock, watched TRL as a kid, or owned Taylor Swift’s country album in CD form. But perhaps the best way to judge which era one belongs to is by the movies that raised them—films that still strike a chord with their stories, their humor, their pop culture references, and even their soundtracks.

The big screen often reflects the society of its time, something that’s certainly true for these Gen X gems. They’re blockbuster comedies that propelled young actors to superstardom, hang-out comedies that questioned the value of success, cyber thrillers that started fictional world wars, and queer rom-coms that skewered binary norms. They spanned a decade, guiding audiences out of the fog of hairspray and neon that was the 1980s, ushering them into the grunge rebellion of the 1990s via Jane Austen adaptations and Cameron Crowe-directed coming-of-age films.

While the best movies often cross generational divides, it’s always good to remember one’s roots. In that spirit, here are 15 of the best Gen X movies (listed in chronological order) that captured a groundbreaking era—not just for cinema, but for the culture at large.

Fast Times At Ridgemont High (1982)
Risky Business (1983)
WarGames (1983)
Heathers (1988)
Do the Right Thing (1989)
Pump Up the Volume (1990)
Boyz n the Hood (1991)
Singles (1992)
Reality Bites (1994)
Clerks (1994)
Clueless (1995)
Before Sunrise (1995)
Hackers (1995)
Trainspotting (1996)
But I’m A Cheerleader (1999)

Fast Times At Ridgemont High (1982)

Cameron Crowe spent a year undercover at a San Diego high school, eventually writing a book about his experiences that he would then adapt into this ‘80s stoner comedy. With Amy Heckerling taking the directing reigns, Fast Times at Ridgemont High was a too-horny-for-its-decade love letter to teen romance and the many sexual epiphanies it inspires. Though Sean Penn’s slacker surfer bro Spicoli is its best-remembered character, Jennifer Jason Leigh’s Stacy Hamilton is its heart—a young girl experiencing life for the first time, guided by peers-turned-mentors with barely more experience than herself. Heckerling may have been forced to cut full-frontal scenes in order to earn an R rating, and the studio may have deemed it blockbuster porn, but the film remains one of the more authentic studies of high school on the big screen. Can you imagine if David Lynch had agreed to direct this thing instead? (Yes, he was approached about it.)

Risky Business (1983)

The film that cemented the image of Tom Cruise donning white briefs and a button-up into our collective pop culture pantheon, Risky Business is a cutting satire, one that dices up the privilege of rich suburban kids and feeds it to audiences with a dose of humor and some ridiculous hijinks. Cruise’s Joel is an overachieving high schooler hell-bent on enjoying his freedom when his wealthy parents leave on holiday. His pursuit of a good time leads to brushes with the city’s criminal underground, including sex workers, pimps, and the seedy company they keep. Despite the very real danger, Joel manages to outmaneuver every predicament, proving if you’re loaded (with money and confidence) escaping consequences really is possible. Tom Hanks reportedly wanted the lead role but, despite some disastrous auditions, Cruise nabbed the part after pestering director Paul Brickman to give him a chance. It’s a good thing too, since the film’s most iconic scene came thanks to the actor—who waxed the floor of Joel’s colonial living room and slid on some socks to guarantee his character’s smooth entrance.

By the way: If the way you remember that iconic dance scene includes Cruise wearing a pair of Ray-Bans, you’re misremembering. A lot of people do it—so many that it’s a prime example of the Mandela Effect.

WarGames (1983)

A twist-filled tech thriller that played on societal fears of the time including cyberwarfare and Cold War fallout, WarGames made such an impression on audiences that it spurred Ronald Reagan to issue a presidential directive. The movie, which was inspired by a trip to the Stanford Research Institute (and the life of Stephen Hawking), film follows David Lightman (Matthew Broderick), a computer genius who accidentally hacks his way into a supercomputer belonging to the U.S. military, setting off a chain of events that could lead the U.S. into a nuclear war with the Soviet Union.

Heathers (1988)

Heathers takes a stick of dynamite to the sticky-sweet John Hughes-era of teen comedies, smothering the optimism of youth in drain cleaner and trading doodled diary entries for forged suicide notes. As dark as that sounds, Heathers could have flirted with even more gruesome imagery; its writer, Daniel Waters, really wanted Stanley Kubrick to direct his coming-of-age comedy. (There’s an homage to Full Metal Jacket in its opening scenes if you know where to look.) Toying with generational values of purity, privilege, and the popular mean girls named Heather who trade on both, the film sees Winona Ryder and Christian Slater playing a pair of outcasts out to spark a bit of anarchy (and maybe, mass murder). Ryder almost didn’t nab the part of Veronica as the actress was fresh off her role in Beetlejuice and considered “not attractive” enough to play the film’s lead. Luckily, a mall makeover can fix even the worst dye job and Ryder was eventually given the chance to crown herself cinema’s ultimate Queen B.

Do the Right Thing (1989)

Spike Lee’s fourth-wall-breaking drama is both a visual time capsule for ‘90s-era racial tensions in America and, unfortunately, a still-timely warning against the stereotypes and prejudices that are still prevalent today. Lee spent just two weeks writing the film’s script, which follows the day in the life of a young Black man named Mookie (Lee) who navigates tribal conflicts in his Brooklyn neighborhood during a sweltering heat wave that pushes a city to its breaking point. Inspired by Alfred Hitchcock’s theories on the correlation between climate and violence, Lee’s masterpiece touches on everything from police brutality to civil rights history and the oppressive cycle of poverty with a sincerity that’s never overshadowed by its funnier moments.

Pump Up the Volume (1990)

Christian Slater incites a teenage revolution, translating his character’s angst and masturbation fetish via a voice distorter on a pirated radio station in Pump Up the Volume. Allan Moyle’s coming-of-age comedy reveled in the nihilism of youth, leaning into themes of free speech and anti-establishment that colored the time and setting them to an indie soundtrack for the ages. Inspired by a classmate who distributed anonymous pamphlets at his school, Moyle hoped to combat the John Hughes rom-coms that dominated the ‘80s. He initially intended for John Cusack to play the role of Mark Hunter, but the actor passed, saying he wanted to do more adult fare after Say Anything. Slater won Moyle over with his Jack Nicholson-esque smirk and acting style—not to mention his commitment to the role.

Boyz n the Hood (1991)

John Singleton’s electric directorial debut—the idea for which sprung from a film school application—made history when it netted the filmmaker a Best Director Oscar nomination, making him the first Black director and the youngest director in history to earn that nod (a record that still holds). At the same time, Boyz n the Hood shocked critics and audiences alike with its gritty, heartbreaking portrait of ‘90s gang culture in South Central Los Angeles. Cuba Gooding Jr., Ice Cube, and Morris Chestnut play a trio of young Black men surviving in Crenshaw amidst turf wars and episodes of police brutality. When tragedy strikes a member of their group, they are forced to confront the hopelessness of their situation. To give the film’s violent scenes a more visceral feel, Singleton wouldn’t warn the cast when real gunfire would be used, ensuring their reactions were authentic.

Singles (1992)

The blueprint for “no plot, just vibes” ‘90s flicks, this Cameron Crowe-directed ode to grunge culture may have birthed the concept for Friends years before Ross, Rachel, Chandler, Monica, Joey, and Phoebe shared apartments and IRL group chats at Central Perk. Filled with cameos from iconic grunge bands like Soundgarden and Pearl Jam and blink-and-you’ll-miss-it appearances from Tim Burton and Paul Giamatti, Singles follows a group of twentysomethings living in an apartment block in Seattle. Though it’s an ensemble film and presented in chapters, Singles largely focuses on the romantic troubles of a coffee shop waitress (Bridget Fonda) and an aspiring rock star (Matt Dillon). And is deserving of its cult status if for nothing else, introducing audiences to the fake grunge group, Citizen Dick.

Reality Bites (1994)

Ben Stiller’s directorial debut just happens to be this quintessential Gen X romantic comedy that avoided marketing itself as such at all costs. That’s probably because it came on the heels of a similar coming-of-age film—Singles—that didn’t bomb, but definitely deflated, at the box office. Cast members like Janeane Garofalo were loathe to assign any generational angst to the story of a group of college grads searching for meaning (and steady-paying jobs) in a post-recession world. But is there anything more ‘90s than the concept of “selling out,” the pop culture power of MTV, and the existence of a still-thriving Radio Shack? Winona Rider and Ethan Hawke play friends-turned-lovers Lelaina and Troy, both struggling to realize their dreams while working coffee shop gigs, musing about the pitfalls of materialism, and chain smoking. It’s the definition of a good hang-out movie complete with Hawke contributing a couple of jams to its soundtrack.

Clerks (1994)

Kevin Smith sold off his comic book collection, maxed out his credit cards, and borrowed money from his parents to make this classic Gen X comedy about a couple of friends working part-time gigs at a video rental store and a Quick Stop grocery mart. When Dante (Brian O’Halloran) is ordered to cover a co-worker’s shift at the convenience store where he works, he and his slacker buddy Randal (Jeff Anderson), come up with various ways of shirking their responsibilities, ultimately leading them to question the direction their lives have taken. While ‘90s comedies often loved to linger in the doldrums of daily life, Smith’s meandering tale almost ended with a shocking character death. Taking inspiration from Spike Lee’s Do the Right Thing, Smith originally planned for Dante to be the victim of a robbery gone wrong, but that ending proved too depressing for the studio.

Clueless (1995)

When 20th Century Fox came courting Amy Heckerling to write a TV pilot about cool teenagers, she thought of her Fast Times character, Jeff Spicoli. Not because he was a stoner, a surfer, or the breakout star of her cult comedy hit, but because of his positivity. “I thought, ‘I’m going to write a character who’s positive and happy,’” she told Entertainment Weekly. “And that was Cher.” Pulling inspo from Jane Austen’s Emma and her real-life studies of Beverly Hills high schoolers, Heckerling transformed her small-screen idea into a female-fronted comedy that would become the blueprint for those that followed. As Cher, a privileged popular girl with a naïve outlook on life and an unwavering belief in the power of a good makeover, Alicia Silverstone was able to make audiences fall in love with her out-of-touch airhead which, in turn, made Clueless a timeless coming-of-age comfort watch. As for what made it totally ‘90s? Besides the fashion and the lingo, Paul Rudd gifted his cast mates with personalized rice grain necklaces once filming was over.

Before Sunrise (1995)

Richard Linklater’s first entry in his Before trilogy was inspired by a real-life meet cute at a Philadelphia toy shop. He changed the setting and employed the help of writer Kim Krizan to pen the script for Before Sunrise in just 11 days. The romantic drama starring Ethan Hawke and Julie Delpy is a subtle, dreamy ode to travel and its ability to push people out of their comfort zones. Hawke and Delpy play two strangers who connect on a train to Vienna, and eventually embark on a swoon-worthy adventure. Filled with intimate vignettes and philosophical conversations, the dialogue is what fuels the fairy tale here—which is important, seeing as Delpy implied she and Hawke had to rewrite most of their scenes to lend a bit more passion to the film. Krizan disputed this, but the actors were given a writing credit on later follow-ups (which earned both actors, plus Linklater, Oscar nominations in 2005 and 2014 for Before Sunrise and Before Midnight, respectively).

Hackers (1995)

This crime thriller treated the internet like the wild west because, when it was made back in the mid-1990s, that’s exactly what it was. Reflecting both the anxieties and possibilities associated with technological free will, Hackers delighted in using dial-up as a plot device while positioning stars Johnny Lee Miller and Angelina Jolie as the kind of hot, rebellious nerds that only exist on film. Operating under codenames like “Acid Burn” and “Lord Nikon,” the group accidentally hacks its way into a conspiracy involving a wealthy oil conglomerate and a tech mastermind on a mission to get rich at any cost. Slick, stylish, and somewhat prescient, the film works thanks to help from real-life hackers who consulted on the script and taught the cast how to convincingly code on camera.

Trainspotting (1996)

Danny Boyle’s dizzying drug odyssey through the streets of Edinburgh was so controversial when it was first released that it prompted U.S. senator Bob Dole to condemn its “moral depravity” during his 1996 presidential campaign. Sure, he’d never actually seen the film, but the rumors of star Ewan McGregor learning how to cook heroin from recovering addicts must have reached his ears at some point. Thankfully, mainstream audiences had better cinematic tastes than Dole, showing up in droves to watch a group of friends and addicts explore the impoverished alleyways of their hometown while confronting classism, systemic injustice, and devastating loss.

But I’m A Cheerleader (1999)

What Gen X teen didn’t question their sexuality after converting to vegetarianism and playing their Melissa Etheridge CDs on a loop? Those behaviors are the catalyst for a stint at a conversion camp in Jamie Babbit’s satirical rom-com, But I’m A Cheerleader. Natasha Lyonne plays Megan, the titular teen archetype and blonde do-gooder from a conservative family who struggles to feel any attraction to her jock boyfriend. Fearing the worst—homosexuality—her parents send her to a therapy camp with a five-step program for praying the gay away. While there, Megan meets a camper named Graham (Clea Du’Vall) and the pair fall in love, ultimately defying her parents and happily living their truth. Babbit’s mom ran a drug rehabilitation program, something she pulled inspiration from when writing the film, and the director modeled the artificial look of life at camp—the intense blues and pinks that defined binary norms of the time—after films like Edward Scissorhands.

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