32 Movies That Helped Define Generation X

John Cusack in Say Anything
(Image credit: 20th Century Fox)

The late '80s and early '90s (for the most part) were the very brief time when Generation X ruled the culture. Movies, including classics like Reality Bites, The Breakfast Club, and so many others, are what helped define the generation, both for better and for worse. So here they are, some of the most important cultural movies of the era.

Ben Stiller in Reality Bites.

(Image credit: Universal Pictures)

Reality Bites

Reality Bites is definitely the movie that best fits the purpose of this list. There are so many ways this movie defines Gen X, from the cast, including Winona Ryder, Ethan Hawke, Janeane Garofalo, and Ben Stiller, who also directed, to the plot about struggling to find purpose, to the music. It's number A1 on any list like this.

Bridget Fonda in Singles

(Image credit: Warner Bros.)

Singles

Seattle in the 1990s. There is nothing more iconic to Gen Xers. Singles brought that scene to the rest of the country. It includes many of the best bands from the city at the time, bands that were themselves defining a big piece of the culture, and also manages to highlight a lot of the angst that the generation also felt at the time.

Molly Ringwald and Judd Nelson in The Breakfast Club

(Image credit: Universal Pictures)

The Breakfast Club

High school in the '80s and '90s was defined on the big screen by director and writer John Hughes, and his impactful film on an entire generation has to be The Breakfast Club. It's a movie that people who grew up in the era still quote endlessly and rewatch whenever it strikes their fancy.

Spike Lee in Do The Right Thing

(Image credit: Universal Pictures)

Do The Right Thing

Spike Lee set the standard for telling the African-American side of the Gen X experience, and he opened up a lot of white eyes with his iconic movie Do the Right Thing. The movie remains just as powerful today as when it hit theaters in 1989, and at a time when only one side of the culture was really shown in movies, it was incredibly groundbreaking and important.

Heathers cast

(Image credit: New World Pictures)

Heathers

There is no darker, more cynical comedy than Heathers. Cynical is often a word used to describe Gen X, so it makes sense that a movie with such a biting sense of humor would be so iconic. Oh - and it stars a few Gen X heroes like Shannen Doherty, Christian Slater, and Winona Ryder.

Richard Linklater talks to the man driving him in Slacker

(Image credit: Orion)

Slacker

The name says it all. Slacker. For years, that was the label that Boomers and even Gen Xers put on the generation. It wasn't ever a fair label, but it stuck for a long time. It turns out, Gen Xers mostly just want to be left alone, but they'll strive just as hard as anyone for what they want. Director Richard Linklater might be a Boomer himself, but he tapped into the culture like few others.

Christian Slater in Pump Up The Volume

(Image credit: New Line Cinema)

Pump Up The Volume

Disillusionment and frustration are definitely two things that Gen X thought about their lives while in high school, and that made Christian Slater's renegade DJ character in Pump Up The Volume an icon. He said out loud what many of us thought in our adolescence, even if we were wrong most of the time.

Parker Posey looking very upset and wearing a sweatshirt that says "seniors" on it in Dazed And Confused.

(Image credit: Gramercy Pictures)

Dazed And Confused

Dazed and Confused might have been about the generation that preceded most of Gen X, but it still spoke to the generation like few other comedies did. Life in the '70s wasn't all that different from high school in the '90s. The internet changed everything for Millennials, but for about 20 years, life was pretty similar for teenagers.

Do Boy (Ice Cube) speaking on LA gang culture in Boyz N the Hood

(Image credit: Columbia)

Boyz N The Hood

Like Spike Lee, director John Singleton's work landed like a bomb on suburban America. Boyz N The Hood is one of the best movies about urban life in the '90s. It was an aspect of life that white America really didn't have any real insight into until Singleton and Lee told us. Boyz N The Hood remains one of the most important movies of the '90s.

John Cusack and Ione Skye in Say Anything

(Image credit: Twentieth Century Fox)

Say Anything

There is no bigger Gen X icon than John Cusack, and the role that most exemplifies that is Lloyd Dobler in Say Anything. It would be impossible to count just how many people took their style and musical tastes from Lloyd. He was a cool as cool got in the era.

michael madsen in reservoir dogs

(Image credit: Miramax)

Reservoir Dogs

Quentin Tarantino was the first director that Gen X really attached itself to. His movies didn't really influence style, or even music, as he used older tunes, but there is a nihilism in his movies that really resonates with those kids who were watching in the early and mid-'90s.

Phoebe Cates gets out of the pool in red bikini in Fast Times at Ridgemont High.

(Image credit: Universal)

Fast Times At Ridgemont High

For many, the first R-rated comedy they really remember watching is Fast Times At Ridgemont High. You didn't have to be in high school to idolize some of the characters, and the movie taught teenagers at the time a lot about the stuff their parents didn't want to talk about.

Leonardo DiCaprio smiles in mid conversation at the dinner table in Whats Eating Gilbert Grape.

(Image credit: Paramount Pictures)

What's Eating Gilbert Grape?

The cast alone from 1993's What's Eating Gilbert Grape? earns it a place on this list. Johnny Depp, Juliette Lewis, and Leonardo DiCaprio have been a part of Gen X's lives forever, it seems like, and this movie is the highlight of all of their early careers.

Jon Cryer in Pretty in Pink

(Image credit: Paramount Pictures)

Pretty In Pink

It might be a little embarrassing to admit just how many people took their fashion cues from Duckie in Pretty in Pink. Unrequited love may be ubiquitous among all generations of humans, but it felt especially acute in the '80s. Once again, we can probably thank John Hughes for that.

A close up of Denzel Washington with an afro in He Got Game

(Image credit: Buena Vista Pictures)

He Got Game

Like so many of his movies, Spike Lee spoke to a generation like few others in He Got Game. Basketball and hip-hop were enormous pieces in the Gen X puzzle, and this movie brought them together for the first time. A soundtrack of almost nothing but Public Enemy? That says it all.

Cher and Dionne dressed in black. and white in Clueless

(Image credit: Paramount Pictures)

Clueless

Between starring in Aerosmith videos and the classic comedy Clueless, Alicia Silverstone is a bona fide Gen X superstar. Her first truly star-making movie was, of course, Clueless. Plus, it made Paul Rudd a star, too.

John Keating (Robin Williams) looks on as his students stand in solidarity with him in Dead Poets Society

(Image credit: Buena Vista Pictures)

Dead Poets Society

One of the movies on this list that took place in an era outside of Gen X is Dead Poets Society. Even though it was set decades before most Gen Xers were born, the movie really spoke to the generation, especially the boys of the era. I can attest to that, without question. Robin Williams was an idol to us, and still is today.

Brian O'Halloran and Jeff Anderson in Clerks

(Image credit: Miramax Films)

Clerks

"I'm not even supposed to be here today," could be the quote that defines the era better than anyone else. At least how we felt at the time. Dante's thoughts and words were our thoughts and words. We were stuck in dead-end jobs, dealing with idiots and dreaming about bigger things, with no idea how to achieve them. At least we figured out most of that in the end.

Liv Tyler, Johnny Whitworth and Renee Zellwger in record store in Empire Records

(Image credit: Warner Bros.)

Empire Records

Generation X was the last generation that really shopped at record stores. By the time we were in our 20s, Napster had changed the game, and we never went back. Working at a record store was the dream of a lot of high school kids, and watching Empire Records gave us all something to strive for, even if most of us fell short.

Eddie Murphy in Coming to America

(Image credit: Paramount Pictures)

Coming To America

Coming to America is, in some way, really on this list to represent all of Eddie Murphy's movies. We grew up with Murphy on SNL and followed him for the next decade, sneaking into his rated R movies, and watching bootleg VHS tapes of his standup. In a way, the pinnacle of his early career was Coming To America, so here it is, standing in for so many classic '80s comedies.

Brandon Lee The Crow screenshot

(Image credit: Miramax)

The Crow

It's hard to know if The Crow would be on the list without the tragic death of Brandon Lee. It was such big news at the time that it made both the actor and the movie he died on the set of iconic. Of course, it also had a fantastic soundtrack that included Nine Inch Nails, The Cure, Rage Against the Machine, and more bands that also helped define the culture of the era.

Ralph Macchio stands with his arms posed in the middle of a karate match in The Karate Kid.

(Image credit: Columbia Pictures)

The Karate Kid

The Karate Kid is now a franchise that has now literally been with many Gen Xers for basically their entire lives. The first movie is legendary and it helped give us all hope that no matter our circumstances, we could win the trophy and get the girl. It didn't always work out that way, but it could, and we appreciated that.

wesley snipes in new jack city

(Image credit: Warner Bros. Pictures)

New Jack City

It's hard to understand those who don't remember the Crack epidemic just how all-encompassing it felt to everyone. D.A.R.E., "Just Say No," and the war on drugs were part of everyday life for teenagers in the '80s and '90s, and it was mostly because of Crack. No movie showed that societal disaster quite like New Jack City did.

Mouth, Mikey, Data and Chunk with the map in The Goonies

(Image credit: Warner Bros.)

The Goonies

The Goonies really might need much explanation as to why it's on this list, of course. It's frankly a little amazing just how enduring the movie has been over the years. It's still a movie that Xers point to as a favorite, many decades after the Steven Spielberg movie hit the big screens. The stars were our age, it was a story we believed could be ours.

Robert Duvall in a car, wearing a police uniform and looking over his shoulder in Colors.

(Image credit: Orion Pictures)

Colors

Like the Crack epidemic, the gang wars in Los Angeles were a part of nightly stories on the network news. You'd have thought the world was coming to an end in South-Central LA. The Bloods and Crips were household gang names. Colors, directed by Dennis Hopper and starring Robert Duvall and Sean Penn, brought that into theaters in the 'burbs in this slightly misguided, but still iconic flick.

Bill and Ted in the booth

(Image credit: Orion Pictures)

Bill & Ted’s Excellent Adventure

One thing we were always on the lookout for was anything afoot at the Circle K. We can thank Ted "Theodore" Logan and Bill S. Preston, Esq. for that. Gen Xers saw this movie over and over and over again in the era, and are honestly still liberally quoting from it today.

Vince Vaughn and other actors from Swingers sitting on a couch with video game controllers in their hands

(Image credit: Miramax)

Swingers

As Gen X got a little older, so did the characters in the movies we revered. Swingers is a perfect example of a movie that came along just as Gen X was graduating from college, trying to live their dreams (and struggling), and hoping to meet that someone special to spend the rest of their lives with. And we all wanted to be as cool as Trent (Vince Vaughn). And we played video games before we went out. But we never really did much swing dancing.

The Lost Boys

(Image credit: Warner Bros.)

The Lost Boys

The Coreys (Haim and Feldman), and vampires. Nothing says "Gen X" like that combo, right? The Lost Boys characters were so cool, whether you wanted to be a vampire or wanted to hunt them. It was all there in The Lost Boys.

A serious looking Christian Bale wears headphones as he walks down a hallway in American Psycho.

(Image credit: Lionsgate)

American Psycho

Generation X has always had a real streak of nihilism to it. Nothing quite on the level as American Psycho, of course, but it still managed to speak hilariously to that feeling. It was dark, and Gen X loved dark, dark humor.

Ron Livingston sits in his cubicle looking worried in Office Space.

(Image credit: 20th Century Studios)

Office Space

Everyone hates their job at some point, as Office Space so eloquently highlights. This was especially acute for Generation X when this movie came out. Mike Judge raised us with Beavis and Butthead in high school and he was there again to usher in our working lives after college.

Winona Ryder and Johnny Depp in Edward Scissorhands.

(Image credit: 20th Century Fox)

Edward Scissorhands

This list wouldn't be complete without a Tim Burton movie, now would it? It represents many of the movies that the director made that spoke to the generation, but this is the one that starred Depp and Ryder, so here we are.

The Youth Gang Competition from I'm Gonna Git You Sucka

(Image credit: MGM)

I’m Gonna Git You Sucka

I’m Gonna Git You Sucka brought a brand new comedic sensibility to the generation, and it remains a uniquely Gen X movie, as there may not be any other generation that has seen it, much less revere it like Generation X.

Hugh Scott
Syndication Editor

Hugh Scott is the Syndication Editor for CinemaBlend. Before CinemaBlend, he was the managing editor for Suggest.com and Gossipcop.com, covering celebrity news and debunking false gossip. He has been in the publishing industry for almost two decades, covering pop culture – movies and TV shows, especially – with a keen interest and love for Gen X culture, the older influences on it, and what it has since inspired. He graduated from Boston University with a degree in Political Science but cured himself of the desire to be a politician almost immediately after graduation.

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