25 movies you should watch to really understand Xennials

Poor Xennials. The post-boomer generation of people born between the mid-1970s and early 1980s face a lot of erasure due to the obsession with millennials and how we're killing every industry. But this generation faced the world with a unique set of traits and values that, if you pay close attention, are extremely evident in the movies that define the era, along with the perfect fashion choices of the '80s and '90s.

The movies have a few themes in common: post-graduate ennui, a distaste for authority and yuppies, "slacker" tendencies, feelings of alienation, a desire to disrupt the norm, punk music, and lots of flannel. You'll also see several entries from Richard Linklater and John Hughes, and multiple appearances by Gen X darlings like Ethan Hawke, John Cusack, and Judd Nelson.

Ben Stiller directed this Gen X masterpiece whose very Gen X thesis is, well, reality bites. In the film, Stiller, Winona Ryder, Ethan Hawke, Janeane Garofalo, and Steve Zahn (a Gen X all-star team) face the challenges of "adulting" in the '90s, even though this was before "adult" was used as a verb. The movie tackled the quintessential Gen X struggles over "selling out," dead-end jobs, and having divorced parents. 

Before Sunrise is a movie-length ode to Gen X love. Ethan Hawke meets Julie Delpy while traveling in Europe, and spend a magical day together talking each other's ears off about anything and everything under the sun. It's a giant dialogue about existential crises and love and what it means to be human. 

This may be the first John Cusack vehicle on the list, but it's most certainly not the last. This Nick Hornby adaptation follows Rob Gordon (Cusack) as a recently dumped record store owner who becomes obsessed with getting in touch with his exes to find out why he's so bad at relationships. The movie is stuffed to the brim with music references and a hilarious Jack Black performance. 

Speaking of music, Empire Records is the iconic Gen X music movie, if only for some of its stars (ahem, Ethan Embry, Liv Tyler, Renée Zellweger). The movie depicts a day in the lives of record store employees at a store in Delaware — the coolest thing you could be in the early '90s was a record store employee. I watched Empire Records for the first time on a bus on a school trip to Six Flags. It was kind of the perfect viewing experience. 

The Breakfast Club's relevance transcends generations, but there's no denying that this John Hughes masterpiece is a pillar of Gen X filmmaking. While Hughes himself was a boomer, he had a distinct ability to capture what it was like to be a high school kid in the '80s.  

Heathers is a perfect satire of that "yuppie" culture Gen Xers hated so much. Winona Ryder and Christian Slater are a Gen X dream team, rebellious, cynical, and... extremely attractive. Heathers is a classic for the ages. 

A few years before he was High Fidelity's Rob Gordon, John Cusack played Lloyd Dobler, a self-appointed "underachiever" who falls for the school valedictorian Diane Court (Ione Skye). The boombox scene is iconic. With the combination of writer-director Cameron Crowe, John Cusack, and "In Your Eyes" by Peter Gabriel, there is no doubting Say Anything's Gen X street cred. 

Cameron Crowe shows up again with Singles, a Gen X romcom for the ages starring Bridget Fonda, Campbell Scott, Kyra Sedgwick, Matt Dillon, and all the grunge music you could possibly imagine. No really. The movie takes place in Seattle, the hub of grunge. Real musicians Eddie Vedder and Chris Cornell appear in the film, too. It's a total time capsule. 

Dazed and Confused is about high school in the '70s, so it captures a specifically Gen X experience. The Richard Linklater film is all about being, well, dazed and confused, coming of age just like, figuring stuff out, man! 

Gen Xers like Kevin Smith were responsible for a boom of indie films during the '90s, and Clerks is perhaps the most iconic of them all. The black-and-white comedy launched Smith's career and kickstarted a trend of meandering, comedic films with hero slackers as the main characters. 

This Chuck Palahnuik adaptation is the story of a regular guy, a cog in the machine, who longs for something more. Ed Norton and Brad Pitt star in Fight Club, which became a phenomenon and somewhat of a manifesto for dudes who didn't get it. Nevertheless, it was definitely one of the most influential movies of the time period. 

Gen X movies were often characterized by a whole gaggle of pretty actors playing a group of friends who recently graduated school and are dealing with all the trials and tribulations of transitioning to adulthood. St. Elmo's Fire is no exception. This movie came complete with Emilio Estevez, Rob Lowe, Demi Moore, Judd Nelson, Ally Sheedy, and more. 

Spike Lee addressed racial tensions in a way that no one else was doing during this time period. Spike Lee plays Mookie, a pizza delivery guy living in Brooklyn with his sister. The film takes place during a summer heat wave and captures a moment in time as well as the crux of a generation's struggles. 

Richard Linklater's cult classic again takes place during a single day and follows a cast of characters as they go about their day in Austin, Texas. If there's one word that many use to sum up Generation X, no matter how accurate it actually is, that word is "slacker." So to say this film is essential viewing in order to understand Gen Xers would be an understatement. 

Straight Gen X comedies don't get as much love as they should. Encino Man stars three iconic Gen Xers, Brendan Fraser, Sean Astin, and Pauly Shore. Brendan Fraser plays a caveman who thaws in the 20th century and learns all about 20th century life from Astin and Shore. But they learn from cavemen Link too. 

What?! Another John Cusack movie? That's right. In Grosse Pointe Blank, he plays a disillusioned hitman who ends up back in his hometown for his high school reunion. Sound like a nightmare and a half? Yeah, well, it is. A perfect, Gen X nightmare. 

A bunch of high school hackers expose a corporate extortion conspiracy in this very "of the time" movie, which stars Jonny Lee Miller, Matthew Lillard, and Angelina Jolie. 

There aren't a lot of expressly Gen X horror movies, but Scream is definitely one of them. It's as scary as it is funny, a parody of the classic slasher film that's simply soaked in irony, just like Gen Xers.  

The only British movie on the list, Trainspotting is one of the best black comedies of the '90s. It addressed themes of drug addiction and poverty in Edinburgh, stars Ewan McGregor, and upset lots of old people with its depiction of drug use, which makes it very Gen X indeed. 

Wayne and Garth are perhaps two of the most iconic slackers of all time. All they want to do is "party on" and bang their heads to Queen's "Bohemian Rhapsody." Wayne's World is a classic for the ages. 

John Singleton's autobiographical film that chronicles teenage life in South Central L.A. is as nuanced and complex as the real-life issues the film addresses. Ice Cube, Cuba Gooding Jr., Regina King, Laurence Fishburne, Angela Bassett, and others round out this simply iconic cast. 

John Hughes is back again, this time with Ferris Bueller's Day Off. Matthew Broderick stars in this instant classic as a bored high school kid who's longing for more. There's hardly a person who hasn't seen Ferris Bueller multiple times at this point.  

No one really talks about it, but Adam Sandler is a total Gen X filmmaker. And while many of his films qualify, there's something about Big Daddy that makes it so Gen X it almost hurts. I think it's because it's about Gen Xers on the cusp of settling down, becoming parents, and starting families. 

Christian Slater plays a high school student from the suburbs, a total angsty loner, who starts an FM radio station and starts a movement. There's almost nothing more Gen X than the combination of Christian Slater, lots of music, and the story of a punk who fights to be heard. 

One of the kookiest Gen X films on the list, Being John Malkovich tackles themes of celebrity and fame. In The Cinema of Generation X: A Critical Study of Films and Directors, Peter Hanson writes that the movie, which is about a portal that regular people can enter to experience the world as actor John Malkovich, is the "wittiest reflection" on the "social shift" of the 1990s, when, "notoriety and fame because interchangeable concepts." He quotes director Charlie Kaufman, who said that the film "comes from the idea of not wanting to be yourself and being envious of other people. There is for sure the idea of looking out in the world and feeling you don't deserve to be there."  

Editor's Note: The article was originally published in April 2020. It has since been updated.