The 25 most iconic Gen-X films

This dark coming-of-age drama is not easy to watch. However, it is riveting in its truthfulness. Teenage sex, underage drinking, raves, and HIV/AIDS were all mainstream topics for Generation X. All that, plus a breakout debut performance from Chloe Sevigny and a notable yet disturbing one from Leo Fitzpatrick, made Kids an entertaining cautionary tale. 

Get used to seeing Richard Linklater on this list. He's arguably the most prominent Gen X director on the planet, and his films seem relatable to those from any wing of the generation. SubUrbia is one Linklater film that tends to get lost in the shuffle among his more well-known efforts like Dazed and Confused (which is not a Gen X film, by the way). Still, the story of some young adults pondering life while drinking and hanging outside a convenience store can be highly entertaining if told correctly, as is the case here. The soundtrack is great, too.

Like Richard Linklater, director Kevin Smith appears a few times on this list. First is this story of a young comic book artist (Ben Affleck) in love with an energetic lesbian (Joey Lauren Adams) while also dealing with issues between him and his longtime best friend (Jason Lee). Complicated love scenarios are frequent in Gen X films, and it doesn't get more complex than this.

Parker Posey was the indie film queen of the 1990s, and she took her turn in a leading role with his underrated cult flick directed by Daisy von Scherler Mayer. Posey's twenty-something Mary is a free-spirited slacker who spends her time hanging at clubs and throwing popular house parties. When her life spins out of control, she needs to find some direction and eventually does as a library clerk.

Not all Gen Xers are slackers. Some are overachievers yet shallow when it comes to materialism and popularity. Say hello to Cher (Alicia Silverstone) and her rich friends, who have their own vernacular and come off ditzy and lost but actually care about things besides clothes, cars, and money. While this was a satirical, over-the-top look at the American high school of the 1990s, Cher was endearing. 

A good number of Gen X-type movies of the 1990s focused on twenty-somethings looking for their place in life. In the case of Rob Gordon (John Cusack), he's a thirty-something unlucky-in-love record-store owner trying to find his way in Chicago. Cusack, whose characters often championed the underdog, is not always likable in the lead role in this movie version of Nick Hornby's book, but there is plenty of realism to Rob. Even in their 30s, people look for direction and fulfillment, professionally or personally. 

This late 1990s film based on Chuck Palahniuk's novel starred Edward Norton and Brad Pitt and was a massive hit with those Gen X outcasts dissatisfied with their jobs — even if they were good ones. The film was also lauded for its portrayal of the overemphasis on consumerism that sprouted in the 1980s and continued well into the '90s. There's an element of deep-thinking asked of the audience — something that became the norm among 1990s movies.

It might not be a stretch to say that the Scream franchise of films defined the horror genre for Generation X. There's plenty of blood, decent murder scenes, and some extremely funny moments. These movies are fun to watch because the humor is just as good as the action and the death. The only downside is that it gave Jamie Kennedy more than 15 minutes of fame.

Another offering from John Cusack. This time as Martin Blank, a paid assassin who returns to his Michigan hometown for the dreaded 10-year high school reunion. It's a quality black comedy about potentially re-inventing oneself and second chances — themes that seemed rather commonplace in 1990s films and Gen X fare. Cusack and Minnie Driver, as Martin's former and possibly present-day love interest, deliver strong performances.

The day-in-the-life storylines are another favorite of Gen X-type films. In this case, it's about teens and twenty-somethings working in an independent record store dealing with the appearance of a celebrity, losing your virginity, blowing the boss' money while trying to solve a problem, and trying to muster up the courage to tell someone you love them. All while the future of the store is on the line. It's far from a perfect film, but Liv Tyler, Robin Tunney, and Renée Zellweger deliver solid performances in a project that offers a buffet of young Gen X issues.

One of the most acclaimed movies of the 1990s (from any genre), Trainspotting has a particularly fond place in the hearts of certain Gen X fans. A black comedy revolving around the lives of twenty-something heroin addicts in Edinburgh captured the seedy aspects of a generation. Though the characters can be vile at times, their struggle to survive and find purpose in life is somewhat admirable. 

Swing music had its time during a fairly lengthy stretch in the 1990s. Swingers helped the movement. Mike (Jon Favreau) is trying to make it as a comedian/actor in Los Angeles while still dealing with the effects of a break-up with his longtime girlfriend. The film also turned Favreau's co-star Vince Vaughn into a marquee attraction thanks to his character's play-it-cool, smart-alecky demeanor that seemed to play well with twenty-somethings.

Hanging out at the mall was not just a girl thing in the 1980s and '90s. In the case of Gen X folk, it was a rite of passage for teens and some young adults, like Brodie Bruce (Jason Lee). Another offering from Kevin Smith, Mallrats doesn't always get the credit it deserves within his "New Jersey Trilogy." It's a goofy film but tends to grow on viewers who still respond to the slacker theme that was a major part of this generation. Just keep that kid off the escalator!

Christian Slater played the quintessential Gen X character to a tee on more than one occasion. Some critics considered him the Jack Nicholson of a generation, at least for a few years. Slater's Mark Hunter is not much for fitting in or conforming to teen life in the suburbs. So, he starts a pirate radio station under the handle of "Hard Harry," drawing outcasts and introverts out into the open to raise the middle finger at the establishment. A stellar alternative rock soundtrack also aids him. 

Social and racial injustice issues involving different generations and age groups came to the forefront in film during the 1980s but perhaps more so in the 1990s. Do the Right Thing is still the film Spike Lee is known most for and could be considered the catalyst for such a movie movement. Lee's tale of racial tension in a Brooklyn neighborhood offered viewpoints from baby boomers and Gen Xers and how different they are.

Based on their iconic Saturday Night Live characters, this beloved Mike Myers-Dana Carvey comedy captured a fair share of the basic Gen X stereotypes. Slackers, stoners, consumerism, and kids who want to live in their parents' basements forever. It made for great comedy with an above-average plot and vision from director Penelope Spheeris, a baby boomer with a brilliant understanding of the generation that followed.

Slacker is like the little independent film that could. It was the first picture that showed the talent of director/writer Richard Linklater. Another day-in-the-life movie chronicling the lives of various mostly twenty-something hipsters, bohemians, and deviants hanging around the streets of Austin, Texas. The dialogue stands out most about the film, covering topics such as UFOs, the JFK death conspiracy, and Madonna's pap smear. 

N.W.A. introduced the world to the hard times and hard living that was going on in Southern California, particularly South Central Los Angeles and nearby Compton, during the 1980s and '90s. No film told the story better than John Singleton's directorial debut. The movie was lauded for its realistic and brutally honest take on the environment. It's also armed with stellar performances from the likes of Cuba Gooding Jr., Laurence Fishburne, and Ice Cube in his film debut.

Another classic from Richard Linklater. Travelers Jesse (Ethan Hawke) and Céline (Julie Delpy) meet on a train headed for Vienna. She's a college student in Paris, and he's an American traveling around Europe to run away from life. They decide to spend the day in Vienna, and sparks fly. Travel, spontaneity, and the potential of something beautiful, especially when it comes to love, are hallmarks of Generation X films. Not many did it better than the movie that spawned two more films: Before Sunset (2004) and Before Midnight (2013). 

"My teen angst bulls—t has a body count." If that doesn't sum up the brilliantly dark and humorous Heathers, we don't know what does. The words of high schooler Veronica Sawyer (Winona Ryder) rang true in this story about a powerful female clique (three of which are named Heather) that secretly hates each other. Add newcomer bad boy J.D. (Christian Slater) to the mix, and Gen X-angst held by plenty of high schoolers around America turns deadly on screen. 

Everybody loves an underdog. Who could not love Lloyd Dobler (John Cusack)? A champion of mediocrity poised to become a star kickboxer. High schoolers in the mid-to-late 1980s enjoyed their keg parties, hanging out with friends, and taking a shot at dating the beautiful girl (Ione Skye) that seemed way out of their league. This Cameron Crowe gem had it all, including the greatest-ever fictional use of a boom box. 

To some film critics and fans, this John Hughes classic is the gold standard for Gen X films. It's among the best when nailing down the insecurity that lingers inside high schoolers of any category. Others believe this film did not age well. Gen Xers are into labels — like branding someone a brain, an athlete, a basket case, a princess, and a criminal.

With Seattle's burgeoning grunge music scene as a backdrop, Singles details the lives of those in their 20s navigating the choppy waters of love. While the cameos are fun and the soundtrack is among the best of all time, strong performances from Matt Dillon, Campbell Scott, and Kyra Sedgwick make this honest romantic comedy from Cameron Crowe shine brighter than most of its era.

Full disclosure: There are stronger overall movies on this list, but what Reality Bites does better than most Gen X films is hit the sweet spot about the question of, "What's next? In this case, director Ben Stiller showcases recent college graduates trying to find their place professionally, personally, and emotionally. Winona Ryder, Ethan Hawke, and Janeane Garofalo all shine — especially when dancing to "My Sharona" in a gas station convenience store.

Like it or not, many in the latter end of Generation X liked to complain. Nothing was their fault, especially their lot in life, whether a slacker or those seemingly content with working dead-end jobs. Nobody summed that up better than Dante (Brian O'Halloran) and Randal (Jeff Anderson): convenience store and video store workers, respectively, who think they are above their jobs yet don't have the drive or confidence to move on and up. Their angst for work and customers is so hilarious, in an often raunchy way, in Kevin Smith's black-and-white, low-budget breakout directorial debut. People are still whining, "I'm not even supposed to be here today."