10 Movies That Defined Generation X

Steve Zahn, Winona Ryder, Ethan Hawke and Janeane Garofalo in “Reality Bites.” Photo Courtesy: Universal/Everett Collection

Apathetic, detached slackers… Generation X — the one that falls between Boomers and Millennials and whose members are born somewhere between 1965 and 1980 — hasn’t always been characterized in the nicest terms.

Let’s go over a few of the movie titles released when Gen Xers were coming of age and learning how to grapple with grown-up life and tedious, underpaid 9-to-5 jobs. And let’s see what — other than cynicism, angst, ripped jeans and grunge music — defined the disaffected generation that gave us Winona Ryder, Ethan Hawke, Julie Delpy and Keanu Reeves.

Be advised that, when it comes to representation, this list could look like it lacks a bit of diversity. Not for nothing, Gen X has been accused of skewing white and straight and of overrepresenting white, college-educated twenty-somethings. We strived for some balance with the selection.

Do the Right Thing (1989)

Rosie Perez and Spike Lee in “Do the Right Thing.” Photo Courtesy: Everett Collection

Spike Lee wrote, directed, produced and even had a role in this movie set on a scorching summer day in Brooklyn. When the owner of the Italian-American pizzeria in the heart of the film’s majority Black neighborhood refuses to hang pictures of Black leaders on his Wall of Fame, conflict arises. Lee managed to capture the discontent and struggles of a younger generation while portraying police brutality and the many intricacies of race relations.

Heathers (1989)

Winona Ryder, Kim Walker, Lisanne Falk and Shannen Doherty in “Heathers.” Photo Courtesy: New World/Everett Collection

Granted, the big hair and bigger shoulder pads the Heathers sport here are reminiscent of a soon-to-be-outmoded ’80s look. Generation X icons Christian Slater and Winona Ryder star in this dark comedy about high school cliques and bullying that became a cult classic. She’s Veronica, the only non-Heather among the mean and popular Heathers. He’s J.D., the mysterious and eternally-clad-in-dark-colors-and-grungy-plaids new student in Veronica’s high school. She has a thing for him and realizes he’s also very much into her. But J.D. definitely has a more wicked side than Veronica could have imagined.

Pump Up the Volume (1990)

Samantha Mathis and Christian Slater in “Pump Up the Volume.” Photo Courtesy: New Line/Everett Collection

Christian Slater finds himself in high school again in this teenage movie where he plays Mark Hunter, a nerdy, shy teenager dealing with a double life. By night Mark is the host of a pirate radio station in which he engages in long, angst-ridden monologues about how “all the great themes have already been used up, turned into theme parks” and how he doesn’t look forward to the future because the ’90s are a “totally exhausted decade where there’s nothing to look forward to and no one to look up to.”

No one knows who the voice on the radio is, but Mark’s words sure pique the attention of the rebellious Nora (Samantha Mathis), who also happens to be his crush. “Why Can’t I Fall in Love” performed by Ivan Neville and “Everybody Knows” by Leonard Cohen make for a very timely soundtrack that also boasts themes by Pixies and Sonic Youth.

Point Break (1991)

Keanu Reeves and Patrick Swayze in “Point Break.” Photo Courtesy: 20thCentFox/Everett Collection

This one is certainly the most adrenaline-fueled title on the list. Academy Award-winner Kathryn Bigelow directs this action-caper in which the undercover FBI agent Johnny Utah (Keanu Reeves) infiltrates a group of surfers led by Bodhi (Patrick Swayze) while trying to identify a band of bank robbers believed to be surfers.

Waves, perfect tans, surfer culture, people jumping out of planes with and without parachutes, and precise 90-second robberies make for a movie about discontent and following a dream. Plus, Keanu Reeves perfects the art of the cocky one-liner with dialogue like “The FBI is going to pay me to learn to surf?”  and “I caught my first tube this morning, sir.”

Reality Bites (1994)

Ethan Hawke and Winona Ryder in “Reality Bites.” Photo Courtesy: Universal/Everett Collection

If we had to choose just one movie to encapsulate how Generation X felt in the ’90s, it would probably be this one. Winona Ryder plays Lelaina, a valedictorian right out of college who’s trying to navigate her life as a grown-up and who wants to have a career as a documentarian. Ethan Hawke is Troy, Leilana’s womanizing best friend and perennial slacker. Ben Stiller, who also directed the movie, plays Michael, a convertible-driving yuppie who works at an MTV-like TV station.

Lelaina is videotaping Troy and their friends Vickie (Janeane Garofalo) and Sammy (Steve Zahn), pursuing her passion for documentaries and trying to capture the struggles of her generation. She also has a relationship with Michael and tries to understand whether a sort of platonic friendship with Troy is all there is to them.

Clueless (1995)

Alicia Silverstone and Stacey Dash in “Clueless.” Photo Courtesy: Paramount Pictures/Everett Collection

This modern-day take on Jane Austen’s Clueless was set in 1990s Beverly Hills and written and directed by Amy Heckerling. Alicia Silverstone plays the ultra-rich and privileged Cher, one of the most popular girls at her high school. She has a good heart, but she’s clueless when it comes to not judging a book by its cover. Stacey Dash plays Cher’s best friend, Dionne, and Brittany Murphy is Tai, the new girl in school and Cher’s new project — Cher feels Tai needs a makeover and better taste in boys.

There’s also a storyline in which the teenage Cher ends up being attracted to her college-aged ex-step-brother Josh (Paul Rudd), which hasn’t necessarily aged well. But Clueless is still a classic when it comes to advanced ’90s tech (brick cell phones and software that coordinates your outfits), fashion (matching plaid skirts and blazers!) and slang.

Before Sunrise (1995)

Julie Delpy and Ethan Hawke in “Before Sunrise.” Photo Courtesy: Columbia/Everett Collection

Richard Linklater (Boyhood) directed and co-wrote this tale about the American tourist Jesse (Ethan Hawke) and the French Céline (Julie Delpy). They meet on a Eurail train and decide to debark in Vienna and spend one night together chatting and getting to know the city — and one another. The romantic film is basically a series of conversations between the two young people and their reflections on life.

In true Linklater fashion, the filmmaker reunited with Delpy and Hawke every decade for the sequels Before Sunset (2004) and Before Midnight (2013) that further explore the relationship between Jesse and Céline.

Trainspotting (1996)

Ewen Bremner, Jonny Lee Miller, Ewan McGregor and Robert Carlyle in “Trainspotting.” Photo Courtesy: Miramax/Everett Collection

Danny Boyle directed this movie and basically put on the map actors Ewan McGregor, Kevin McKidd, Johnny Lee Miller and Kelly Macdonald. Based on an Irvine Welsh novel, the movie follows a group of friends and heroin addicts living in the suburbs of Edinburgh. McGregor plays Trenton, a 26-year-old living with his parents who has no prospects in life whatsoever.

Other than its commentary on how to choose life in an overwhelming world of consumerism, the movie also has the kind of soundtrack — with themes by Iggy Pop, Blur, Lou Reed and Elastica — that would become a referent in itself.

Martín (Hache) (1997)

Juan Diego Botto and Eusebio Poncela in “Martín (Hache).” Photo Courtesy: Strand Releasing/Everett Collection

Let’s add a Spanish-Argentinian co-production to the mix. When teenager Hache (Juan Diego Botto) overdoses in Buenos Aires, his fed-up mom decides it’s time for him to spend some time with his dad Martín (Federico Luppi) in Madrid. Hache, who his parents think may have tried to commit suicide, doesn’t do much and is primarily obsessed with his ex, his guitar and getting high. Martín and Hache have long conversations about literature and the meaning of longing for your home country. “Your country are your friends. And that’s what you miss, but it fades away,” says the expat Martín.

Co-written and directed by Adolfo Aristarain, the movie explores the idea of identity and finding yourself from the perspective of Hache, who debates between two cities and two different chances at life.

High Fidelity (2000)

Jack Black, Todd Louiso, John Cusack and Lisa Bonet in “High Fidelity.” Photo Courtesy: Everett Collection

Let’s wrap things up with this story based on a Nick Hornby novel and directed by Stephen Frears. John Cusack plays Rob, the heartbroken owner of an independent record store in Chicago. Rob and his employees — the brazen Barry (Jack Black) and the knowledgeable Dick (Todd Louiso) — take melomania and musical snobbishness a tad too seriously. But through them, we listen to all sorts of good tracks like “Dry the Rain” by The Beta Band and “Oh! Sweet Nuthin'” by The Velvet Underground. All that while Rob tells the audience about his top five breakups.

Also, Hulu recently adapted this story in the form of a TV show set in current-day Brooklyn starring Zoë Kravitz as Rob. Kravitz’s real-life mom, Lisa Bonet, played a role in the original movie. The series sure has more diversity than the original movie and is worth watching for many reasons, but the perfectly curated soundtrack is a big one.