The Best Movies to Watch about the 90s

The 1990s were an important, transitional decade for me. As a Gen Xer, I was a teenager for the first half of the decade and in my early 20’s for the second half.

As a student of film I wanted to write on the best movies about the decade. This is not a list of the best movies of the 90’s, it’s the best movies about the 90’s. Films that captured the values, attitudes, and culture–the zeitgeist of the era. These aren’t just good movies, they are instructive about the decade.

I’ve picked 11 films that capture what everyday life was like in one of my favorite decades. We will go through them year by year from beginning to end.

Slacker (1991)

Slacker didn’t come up with the term, but it made it into a whole vibe. Richard Linklater’s indie is weirdly addictive: it follows dozens of bizarre Austin characters through a single day, bouncing from a guy ranting about alternate realities to someone literally trying to sell Madonna’s pap smear. There’s no plot, just pure people-watching as the camera drifts from one conversation to the next.

It sounds like it shouldn’t work, but it’s fascinating in that “I can’t look away” kind of way. Every character feels like someone you’d overhear at a coffee shop and want to eavesdrop on. The movie ended up defining Generation X’s aimless mindset, turning ‘slacker’ from an insult into a way of life.

It was the first movie to really capture Gen X slacker culture on screen, bottling that post-Cold War moment when a whole generation suddenly had a future but no idea what to do with it. It nailed the choice paralysis, anti-corporate attitude, and everyday boredom that couldn’t exist in the ambitious ’80s or digitally connected 2000s. It’s basically the blueprint for multiple indie films that came after.

Singles (1992)

Singles is basically a time machine to 1992 Seattle, when grunge ruled the scene. Cameron Crowe’s romantic comedy follows a group of twentysomethings living in the same apartment complex, fumbling through relationships with all the awkwardness you’d expect. There are answering machine games, the uncertainty of when to call someone back, and all the little rituals of dating. Singles is charming and funny, with characters you actually root for, like the coffee shop worker who can’t get over her self-absorbed musician boyfriend, or the couple so focused on playing it cool that they almost lose each other.

But what really makes it essential is the soundtrack and atmosphere. Members of Pearl Jam, Soundgarden, and Alice in Chains actually appear on screen, and every frame captures early ’90s Seattle: the fashion, the coffee culture, the whole vibe. It’s the perfect snapshot of the grunge scene at its peak, right before Nirvana became huge and MTV turned Seattle into a brand. You get a sweet, relatable rom-com and a front-row seat to one of music’s most important moments. It’s lightning in a bottle.

Wayne’s World (1992)

Wayne’s World is ridiculously quotable and still holds up as one of the funniest comedies of the decade. Mike Myers and Dana Carvey play two metalhead buddies hosting a public access show from a basement in Aurora, Illinois, and their chemistry is perfect—every scene with them just riffing feels effortless. The plot is simple (TV exec wants to commercialize their show, hijinks ensue) but it’s really an excuse for non-stop gags, fourth-wall breaks, and random detours like the iconic “Bohemian Rhapsody” car singalong. It’s hilarious in a way that doesn’t feel dated.

But it also nails something specific about early ’90s culture: the tension between staying authentic and “selling out,” the DIY spirit of cable access TV, and suburban kids creating their own weird media before the internet made that normal. It also gave suburban metalhead culture its moment in the spotlight, showing that the ’90s weren’t just about Seattle grunge or LA glamour. It’s both a love letter to and a parody of youth culture, managing to be sincere and ironic at the same time, which is peak ’90s. Plus, it gave us catchphrases we still use decades later. Shyeah, right!

Clerks (1994)

I can’t tell you how many times I’ve watched this movie. Clerks is Kevin Smith’s grainy black-and-white debut about a terrible day at a New Jersey convenience store, and it’s way funnier than that sounds. Dante gets called in on his day off and spends the entire shift dealing with nightmare customers, debating Star Wars with his slacker buddy Randal from the video store next door, and screwing up his love life. The dialogue is razor-sharp—these guys riff on everything from ex-girlfriends to pop culture to the hell of retail work, and it feels like conversations you’ve had with your friends at 2 AM. It’s funny but also brutally real about dead-end jobs and feeling stuck.

What makes it essential is that Smith shot it for $27,000 on credit cards at the actual convenience store where he worked, proving you could make a hit movie with no money if the writing was good enough—it inspired an entire generation of DIY filmmakers. It captured that mid-’90s slacker attitude perfectly: smart people trapped in dumb jobs, complaining endlessly but never quite doing anything about it. It’s the most authentic snapshot of retail hell ever put on film, and it still resonates with anyone who’s ever felt stuck. If you can’t get enough 90s Kevin Smith, watch Mallrats and Chasing Amy.

Reality Bites (1994)

Reality Bites is a definitive Gen X movie, and it’s easy to see why it hit so hard. Winona Ryder plays a recent college grad trying to make a documentary about her friends while working at a demeaning and creatively stifling job, caught between her slacker poet crush (Ethan Hawke) and a stable corporate guy (Ben Stiller). The love triangle works because the stakes feel real. It’s not just about romance, it’s about choosing between artistic integrity and paying rent, between the guy who gets you and the guy who can actually support you. The dialogue crackles with ’90s references and the cast has great chemistry, making it entertaining even when they’re being insufferable twentysomethings.

But what makes it uniquely ‘90s is how it captures that post-Cold War moment when Gen X had cultural freedom but economic uncertainty: these characters agonize over ‘selling out’ even while struggling to pay rent, caught between Boomer prosperity they can’t access and an unclear future. The selling out debate that drives the plot reflects genuine stakes—not later dot-com abundance, but the anxiety of educated people facing limited options. It couldn’t have been made before or since.

Empire Records (1995)

Empire Records is a cult classic about one chaotic day at an independent record store, and it’s pure ’90s comfort food. The ensemble cast plays a group of misfit employees trying to save their beloved shop from being bought out by a soulless corporate chain. There’s an embezzlement scheme gone wrong, a shoplifting pop star, a rooftop protest and multiple romantic entanglements, all set to a killer ’90s alt-rock soundtrack. It’s messy and earnest in the best way, with characters you care about even when they’re being dramatic.

What makes it resonate is how it treats the record store like a second home, a place where music-obsessed misfits could actually belong. This was 1995, when big chains were steamrolling independent shops, and the movie tapped into real fears about everything becoming corporate and bland. The whole ‘fight the man, find your people through music’ thing was peak ‘90s idealism, even if the movie’s version is way more romantic than the reality of working retail ever was.

Friday (1995)

Friday is Ice Cube’s laid-back comedy masterpiece about one day in South Central LA. Cube plays Craig, a guy who just got fired and spends the entire day on his porch with his buddy Smokey, watching the neighborhood unfold around them. It’s simple—they smoke, they talk, they deal with a drug dealer demanding money—but the chemistry between Cube and Chris Tucker is electric, and the parade of eccentric neighbors keeps things fresh. It’s genuinely hilarious, quotable as hell, and has a surprising amount of heart beneath all the chaos.

What makes it essential is how it captured mid-’90s West Coast hip-hop culture without the drama or violence that dominated other urban films at the time. This was Ice Cube (former NWA member) choosing to make a comedy that showed everyday Black life in a way that felt authentic and human, not sensationalized. It became a cultural phenomenon that spawned two sequels and introduced a whole generation to a specific vernacular and vibe. It’s a snapshot of a community, a time, and a culture, wrapped up in one very funny Friday afternoon. Plus, it’s just a good hangout movie.

Clueless (1995)

Clueless captured and popularized the shift in mid-’90s teen culture from grunge to prep, and it’s still charming and funny today. Alicia Silverstone plays Cher, a privileged Beverly Hills high schooler who spends her days perfecting her outfits, matchmaking her teachers, and giving makeovers to anyone. The plot is based on Jane Austen’s Emma, but you’d never know it from the Valley Girl slang and computerized closet. Cher’s journey from shallow fashionista to someone with genuine empathy is surprisingly sweet. The cast is perfect: Paul Rudd as her socially conscious ex-stepbrother Josh, Donald Faison and Stacey Dash as her best friends. It’s hilarious, with razor-sharp one-liners that still get quoted today.

But what makes it essential is how it defined a specific strand of ‘90s youth culture, one that embraced colorful optimism over grunge angst. The preppy fashion, the cell phones, the obsession with popularity, this was teen culture running parallel to Seattle flannel toward something brighter and more playful. It created its own language (“As if!”) and aesthetic that defined the rest of the decade. It’s the ultimate high school movie that manages to be both satirical and sincere.

Kids (1995)

Kids is the polar opposite of Clueless. Larry Clark’s film presented itself as the unfiltered reality of NYC street youth, and whether or not you buy that, it’s impossible to look away. It follows a group of skateboarders through one summer day as they drift through Manhattan: Telly is obsessed with deflowering virgins, while his friend Casper and their crew drink, do drugs, and skateboard through the city with zero supervision. When Jennie discovers Telly gave her HIV, she spends the film desperately trying to find him. Shot with handheld cameras that feel almost documentary-like, it’s grainy and viscerally real in a way that still feels shocking.

There’s something hypnotic about watching these kids navigate their world—it’s compelling, like stumbling into someone else’s life without permission. What makes it essential is how it captured a specific slice of mid-‘90s youth culture that mainstream films mostly ignored: the skate scene, the rave parties, the baggy clothes, the casual nihilism. It’s one of the most controversial movies of the decade, earning an NC-17 rating and sparking debates about exploitation versus truth. While Clueless showed teens as witty fashion plates, Kids showed a rawer vision that was just as stylized, only in the opposite direction. It’s unforgettable, even if you’re not sure what you just watched.

Can’t Hardly Wait (1998)

Can’t Hardly Wait is the ultimate late-’90s graduation party movie, and it’s pure nostalgic comfort. The film takes place at one wild house party where Preston finally has his chance to confess his four-year crush on Amanda (Jennifer Love Hewitt), who’s just been dumped by her jock boyfriend. Meanwhile, nerdy William plots revenge on his bully, wannabe rapper Kenny tries to lose his virginity, and Preston’s antisocial friend Denise gets locked in a bathroom with Kenny. It’s got multiple storylines weaving through the chaos, and they all work. It’s funny, sweet, and genuinely rewatchable.

The ensemble cast has great chemistry, and there are enough quotable moments and subplots to keep things entertaining. What makes it a time capsule is how it captures late-‘90s teen optimism right before Y2K anxiety hit: these kids are earnest, romantic, and still living in a world of landlines and mix tapes. It’s peak late-‘90s teen movie—glossy, hopeful, and unironic in a way that wouldn’t survive the 2000s. Plus, it’s a fun party movie.

Office Space (1999)

Office Space is Mike Judge’s cubicle comedy that became the defining workplace satire of the ’90s. Ron Livingston plays Peter, a programmer at a soul-crushing software company who’s so miserable he goes to a hypnotherapist—who dies mid-session, leaving Peter permanently relaxed and completely checked out. He stops caring, shows up late, ignores his boss, and somehow gets promoted while his hard-working friends get downsized. The movie is hilarious and iconic from beginning to end.

What makes it essential is how it captured late-’90s corporate culture: the downsizing consultants, the cubicle farms, the eight bosses asking about cover sheets, the “Is this good for the company?” question. It showed white-collar work as psychological torture. It became a cult classic because everyone who’d ever worked in an office saw their own nightmare reflected back. Twenty-five years later, it hasn’t aged a day. It’s the definitive portrait of late-’90s office malaise.

There you have it, the movies I think best represent the 90’s. Economic boom and idealism, anti-corporate/anti-establishment values, generational self-awareness and some aimlessness were the big hallmarks of the era. It was a special time, after Cold War paranoia but before Y2K, Columbine, 9/11 and entering the digital age changed American culture.

I wanted movies that captured a generation in their ordinary lives: a day at a convenience store, a day on a porch, a graduation party, from grunge to prep, from urban to suburban, I tried to cover a lot of real ground. Try watching one of these now — do you see 1990s values still echoed today?