Content Warning: The following article contains discussions of suicide, addiction, and misogynistic language.

Ah, Generation X. Caught between the Boomers and Millennials, they were known in their day for rallying against societal norms, corporate interests, and generally mainstream anything. "Damn the man" was their trademark because (aside from emphasizing non-conformity), this generation didn't care what you think – everything sucked, anyway.

Related: Movies That Define Gen X, From 'The Goonies' to 'Reality Bites'

Maybe Gen Xers' angst was fueled by the hyper-emotive tunes of their time, but for whatever reason, tons of these movies either feature music in their storylines or (at the very least) have wicked-rad soundtracks. So, dust off your Doc Martins and find your favorite thrift store cardigan: it's time for some serious lessons in uncertainty.

Updated on November 9th, 2022, by Hannah Saab:

With the recently released film, Clerks III, and the upcoming TV series, T3 Trainspotting 3: The Blade Artist, it's clear that there's continued interest in any spinoff, sequel, and more titles inspired by the best Gen X movies. The angstiest among the classics from the 90s and early 2000s can easily transport viewers back to the most memorable parts of their childhoods or teenage years, which is why it's great that there are so many to choose from.

'Reality Bites' (1994)

In what many consider to be the quintessential Gen X film, Ethan Hawke, Winona Ryder, Janeane Garofalo, and Steve Zhan star as four roommates trying to navigate lives after graduating from college. Directed by Ben Stiller (who plays the antithesis of the rest as a money-driven jackass), the film manages to capture the essence of the 90s in a way no other movie does.

While there is a fair share of laughs to be had, there's also an uncomfortable amount of awkward moments, highlighting the undercurrent of insecurity that permeates the narrative like a spray of CK One. A thoroughly modern tale, complete with HIV scares and coming-out sagas, Reality Bites goes to show how insecurity can hinder possibility. If that isn't angsty, nothing is.

'Do The Right Thing' (1989)

Written and directed by Spike Lee and starring Giancarlo Esposito, John Turturro, Samuel L. Jackson, Rosie Perez, and Danny Aiello, this groundbreaking film is angsty for good reason: it centers around disturbing levels of racism in Brooklyn.

Sounds fun, eh? Actually, it's magnificent. The theme of social injustice is juxtaposed with solid jams and bright, cheerful lighting and colors, perhaps making a comment on how folks generally try to gloss over anything they don't want to face. One thing is for sure: the ending is not what audiences saw coming.

'Trainspotting' (1996)

Based on the phonetically written novel by Irvine Welsh, Trainspotting is a masterpiece of 90s Gen-X culture. Starring Ewen McGregor and co-starring Jonny Lee Miller, Robert Carlyle, and Ewen Bremner, the story surrounds a group of characters addicted to heroin and their hapless attempts to both get rich and get clean – not necessarily in that order.

Directed by Danny Boyle, the film is like a time capsule of Gen X anxieties, trends, and grimy underbellies. It also easily has one of the best soundtracks ever assembled.

'High Fidelity' (2000)

The film stars John Cusack as an obsessive, self-centered, and all-around unlikable Gen X dude who can't hold down a relationship. Instead, he throws himself into saving his beloved record shop, which is struggling with modern times. Classic music angst.

High Fidelity also features Jack Black, Todd Louiso, Iben Hjejle, and (of course) Joan Cusack. What's fun is that while Zoë Kravitz plays the titular role in what was more than a gender-swapped remake, it's her mother, Lisa Bonet, who is the love interest in the original.

'Poetic Justice' (1993)

In this classic Gen X movie, directed by the late, great John Singleton, Janet Jackson and Tupac Shakur play two artists who want to escape their tragic and often violent environments. Through fate, they meet and embark on a road trip so filled with angst, disdain, and sexual tension, you can sense it all through the screen.

Obviously, with stars like that, you know the soundtrack is amazing. To add to the emotion, however, Poetic Justice also features poems by Maya Angelou, which basically makes it the most lyrical film ever made.

'Mad Love' (1995)

Drew Barrymore and Chris O'Donnell star in another road-trip movie, only unlike in Poetic Justice, these two characters are in mad love. After a brief stint in a mental health facility, Casey (Barrymore) gets sprung by her straight-laced boyfriend (O'Donnell), and the two of them take off, only to return when Casey's moods destabilize, and she finds herself in deep distress.

Romantic? Yep. Angsty? Absolutely. With so much uncertainty looming on the horizon for Casey, these two try to make the most of the time they have together, but throughout, audiences and protagonists alike know that all good things must come to an end.

'Empire Records' (1995)

Liv Tyler, Renée Zellweger, Robin Tunney, Ethan Embry, and Rory Cochrane all play cool kids who work in an even cooler record store called, you guessed it, Empire Records. But, looks can be deceiving, as audiences soon find out that behind their beautiful exteriors, each and every character has some deep, angsty stuff going on.

From slut-shaming and parental pressures to a suicide attempt and a fake funeral, this comedy manages to tackle some dark stuff, all to a soundtrack that's so b-side 90s cool kid that chances are you haven't even heard of most of the bands.

'So I Married An Axe Murderer' (1993)

So I Married An Axe Murderer is an underrated comedy starring Mike Myers and Nancy Travis, and is about love, trust, and outright paranoia. In it, Charlie (Myers) is a coffee house poet/singer who falls in love with Harriet (Travis), a hard-hearted harbinger of haggis (she's a butcher).

It's too bad Charlie thinks Harriet is an ax murderer. In fact, even Charlie's folks live in some form of dread: his mom believes every word of the bleak tabloids, and Charlie's dad thinks the world is ruled by a secret society of five men who control the entire world, Colonel Sanders included. If that sounds familiar, it's because the film is the impetus for The Pentaverate.

'Hackers' (1995)

When "Zero Cool" (Jonny Lee Miller) is a kid, he gets busted for hacking into the New York Stock Exchange and is banned from touching the keys until he turns 18. Immediately after his long-awaited b-day, he gets at it again under the handle "Crash Override."

In comes Angelina Jolie as his new online nemesis, "Acid Burn." Soon, the two hook up to thwart another hacker's plans to unleash a catastrophic computer virus. Oh, and the Secret Service is after all of them. It's non-stop angst. Fun fact – Miller and Jolie met on set and later got married.

'Office Space' (1999)

Ron Livingston, Ajay Naidu, Jennifer Aniston, and Gary Cole star in this nightmare of a film about what happens when Gen Xers find themselves working for the man.

What transpires is one of the most infuriatingly relatable films of all time for anyone who has ever had a thankless, joyless, soul-sucking, low-level job where the view is the adjoining cubicle. The film also boasts some of the best Gen X movie quotes in cinematic history, so if you could just go ahead and watch Office Space, that'd be great.

'The Breakfast Club' (1985)

Here we have the OG of Gen X films, featuring the Brat Pack that started it all. Written by John Hughes, The Breakfast Club centers around a group of mismatched high school kids (played by none other than Molly Ringwald, Emilio Estevez, Ally Sheedy, Judd Nelson, and Anthony Michael Hall) who all end up in the same weekender detention together. Not cool!

Everyone in the story has problems – and lots of 'em. After an entire Saturday together, however, the group bonds over that exact message. The angst! The uncertainty! The 80s soundtrack!

'Singles' (1992)

In this Cameron Crowe-directed Gen X music movie to end all Gen X music movies, Janet (Bridget Fonda) falls for struggling grunge musician, Cliff (Matt Dylan) and has no idea how to navigate her love for an inaccessible man.

Adding to the problem is that they both live in the same apartment complex, along with four other singles, and all are looking for bona fide, meaningful relationships. All anyone really needs to know about this film, however, is that it is set in 1992 Seattle and features members of Soundgarden, Pearl Jam, and Alice in Chains. You'll think you've died and gone to grunge heaven.

'Clerks' (1994)

Written and directed by Kevin Smith, Clerks is a black-and-white low-budget classic that perfectly captures slacker culture. It follows store clerks Dante Hicks (Brian O'Halloran) and Randal Graves (Jeff Anderson), as they spend their workday doing anything but being responsible, choosing instead to think about their girlfriends, upcoming parties, and the comfort of home.

With an entire day at their disposal and no desire for anything but fun, the film embodies the supposedly new movement known as "quiet quitting." Gen Xers have been familiar with it all along, as they had wacky protagonists like Dante and Randal to lead the way.

'Mallrats' (1995)

Yet another Generation X movie by Kevin Smith, Mallrats is a box office flop that became a beloved cult classic. It depicts Jay (Jason Mewes) and Silent Bob's (Smith) antics in a local mall after they're broken up with by their girlfriends. Set one day before Clerks, the movie is the second entry in Smith's Askewniverse.

It's obvious to any Gen Xer who has seen this film at this point that its main draw today is the way it reflects a generation's love for shopping malls. Once the center of most social activities for teenagers, the glory days of the shopping mall (where anything seemed possible) are now over – not for Jay and Silent Bob, though.

'Fight Club' (1999)

Arguably the representation of angst in the form of a Gen X movie, Fight Club is a film that needs no introduction (and can't be talked about anyway). Director David Fincher's award-winning masterpiece tells the story of the unassuming burnt-out worker called the Narrator (Edward Norton) who meets someone who changes his life forever, the soap salesman Tyler Durden (Brad Pitt).

It's a film known for its brilliant twist, stellar cast, and, most of all, its timely critique of rampant consumerism and capitalism's role in the decline of society. It captured the disillusionment, fear, and growing anger around systemic issues, and is still just as relevant and worth watching again today.

Next: Great 90s Movies That Time Forgot