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 did not care what you think – everything sucked, anyway.
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.
Reality Bites (1994)
.jpeg?q=50&fit=crop&w=1500&dpr=1.5)
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. Streaming now on Prime and Apple TV.
Angstiest banger: “I’m Nuthin” -– Ethan Hawke
Do The Right Thing (1989)
Written and directed by Spike Lee and starring Giancarlo Esposito, John Turturro, Samuel L. Jackson, Rosie Perez, and Danny Aiellothis groundbreaking film is angsty for good reason: it centers around crazy levels of racism in the Bronx.
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 do not want to face. One thing is for sure: the ending is not what audiences saw coming. Stream it on Prime, today.
Angstiest banger: “Fight The Power” -– Public Enemy
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 Carlyleand Ewen Bremnerthe story surrounds a group of heroin addicts and their hapless attempts to both get rich and get clean – not necessarily in that order.
Streaming now on Pluto TV, Prime, and Roku, and 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.
Angstiest banger: “Perfect Day” – Lou Reed
High Fidelity (2000)
The film stars John Cusack as an obsessive, self-centered, and all-around unlikable Gen X dude who can not 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 Hjejleand (of course) Joan Cusack. What’s fun is that while Zoë Kravitz plays the titular role in what was more than a gender-swapped remakeit’s her mother, Lisa Bonet, who is the love interest in the original. See it now on Prime and Disney +.
Angstiest banger: “Town Called Malice” – The Jam
Poetic Justice (1993)
In this classic Gen X film, 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. Streaming now on Peacock.
Angstiest banger: “Again” – Janet Jackson
Mad Love (1995)
Drew Barrymore and Chris O’Donnell star in another road-trip movie, only unlike in Poetic Justicethese two characters are in mad love. After a brief stint in a mental hospital, 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? Yerp. 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. Streaming now on Netflix.
Angstiest banger: “Ultra Anxiety” – Madder Rose
Empire Records (1995)
Liv Tyler, Renée Zellweger, Robin Tunney, Ethan Embryand 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 shit 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. Stream it now on Hulu and Prime.
Angstiest banger: “Sugar High” – Coyote Shivers
So I Married An Ax Murderer (1993)
Streaming now on Hulu and Prime, this underrated comedy, starring Mike Myers and Nancy Travis, 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.
Angstiest banger: “This Poem Sucks” – Mike Myers, Paul Sanchez, David Knowlesand Carl Rusk
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. ” Yep.
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, and it’s streaming on Roku. Fun fact – Miller and Jolie met on set and later got hitched.
Biggest banger: “Cowgirl” – Underworld
Office Space (1999)
Ron Livingston, Ajay Naidu, Jennifer Anistonand 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 most quotable lines in movie history, so if you could just go ahead and stream Office Space on Prime, that’d be great.
Angstiest banger: “Shove this Jay Oh Bee” – Canibus with Biz Markie
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 Nelsonand 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! See it today on Prime and Hulu.
Angstiest banger: “Don’t You Forget About Me” – Simple Minds
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 Jamand Alice in Chains. You’ll think you’ve died and gone to grunge heaven. Streaming now on Prime and Vudu.
Angstiest banger: Considering the lineup, there are far too many to pick just one.
Read Next