The best characters from Gen-X films

There are plenty of employees of the indie hip Empire Records to choose from. Yet, the most genuine and relatable seems to be A.J. (Johnny Whitworth). He's a good worker, a reliable friend, and completely in love with co-worker Corey (Liv Tyler) but afraid to let her know. Sure, he's a typical character in the realm of romantic and teen comedies, but there's a good chance the viewer has been in his shoes. 

To most members of Generation X, life in the 1990s was nothing like that of Cher (Alicia Silverstone) and her rich friends from Bronson Alcott High School. That said, Cher is one of the more iconic characters in the history of Gen-X cinema. Clueless is one of the great teen classics, and high-schoolers at the time, regardless of monetary or social status, found themselves using terms like "as if," "jeeping," and "cake-boy." They can thank Cher for it all.

Musicians span every generation. In the case of Citizen Dıck frontman Cliff (Matt Dillon), he's not very good at his job or being a boyfriend to Janet (we'll get to her). However, he's passionate about music and feels most comfortable and confident amid others in the budding Seattle music scene of the late 1980s and into the '90s. Cliff would be a great cartoon version of himself, not quite a slacker but not yet ready to give up on his dream and grow up.

Heather Chandler (the late Kim Walker) is the ultimate "mean girl." She's the Queen Bee at Westerburg High and rules the group of "Heathers" that owns the school. She makes life miserable for just about everybody and doesn't care. Heather Chandler is also about domination, which is not necessarily a trait of most Gen-Xers. She's ambitious and knows how to get what she wants. She also happens to have most of the best lines in the movie.

It's the role that shot Vince Vaughn into Hollywood stardom. Single, Gen-X males in their 20s thought Trent was "money" and wanted to be like him. You know, they started dressing like they lived in the 1940s, quaffed their hair, and took swing dance lessons. Trent is also a goofball. He's confident but talks a big game and thinks he's cooler than life, even if he isn't. 

Writer, director, and producer Kevin Smith gave us plenty of memorable Gen-X film characters. Brodie (Jason Lee) is one of the best. He's a slacker with a sharp wit and comic book obsession. He also likes to waste his time hanging out at shopping malls (he "loves the smell of commerce in the morning" but is not happy with the kid playing on the escalator). Brodie might not have any immediate direction, but he's funny and sharp enough to eventually better himself.

The "idea" of Tyler Durden (Brad Pitt) made for one of the most iconic Gen-X film characters. This confident yet neurotic and somewhat sociopathic personality consumed our Narrator (Edward Norton). That was the point. Tyler Durden is the type of person an introvert or strait-laced individual might want to channel. At one time or another, a young Gen-Xer wanted to be like somebody else.

If Trent is, for lack of a better term, an *@&hole, then Mike (Jon Favreau) is the everyman worth rooting for. The "guy behind the guy" is trying to find his way professionally and personally in a new city while hoping to get over the breakup with a longtime girlfriend. Having the guts to strike out on your own was a common trait of young Gen-X folks, and Mike is doing that in a serious moment of self-doubt. We've been there. Plus, who knew Favreau was such a good swing dancer? 

The Gen-X film universe is filled with twenty-somethings trying to find their way through life. So, it's rather refreshing to see someone in their 30s, Rob Gordon (John Cusack), struggling to find his place. Record-shop owner Rob struggles to sustain a romantic relationship and doesn't have much self-confidence unless we're talking about creating stellar "Top 5" lists or mastering useless pop-culture tidbits. 

Kids is not an easy movie to watch. The breakthrough performance from the acclaimed indie film was Chloë Sevigny's turn as Jennie. She's a good girl at heart and quite smart, but she faces the consequences of losing her virginity. Jennie is meant to be a cautionary tale in perhaps the most honest picture of the genre from the 1990s.

Christian Slater was a Gen-X film favorite (Heathers, anyone?), but he truly shined as an introvert, not hip on conforming to the everyday suburban ideals of his community or high school in this Allen Moyle favorite from 1990. So, why not start a pirate radio station, think up a cool handle like "Hard Harry," and begin a mild revolution of outcasts? Critical thinking was "in" among Generation X, and it was OK to shun the system. Mark and Hard Harry taught us that. Plus, he backed it up with an awesome alt-rock setlist. 

Steve's professional life is going pretty well for most of this Cameron Crowe Gen-X classic. He's trying to solve the gridlock problem in Seattle with the idea of a Supertrain (give people great coffee, great music ... they will park and ride). It's love that Steve (Campbell Scott) is still trying to figure out. Specifically, whether to get really serious with his new girlfriend, Linda (Kyra Sedgwick). 

Joey Lauren Adams shines as the outgoing, sassy, confident lesbian in perhaps the most poignant of Kevin Smith's films (sorry, Jersey Girl). Sure, Alyssa has her vulnerabilities, but she's an empowered female character that should be more celebrated within the Gen-X film genre. Though she has her flaws, like the rest of us, it's rather easy to see why Holden (Ben Affleck) fell in love with her in a matter of minutes. If only she were better at Skee-Ball. 

Party Girl has earned cult status since its 1995 release. Mainly because Parker Posey is brilliant in the lead role of Mary, a New York City twenty-something with no direction but an insatiable appetite for a good time. Eventually, she's forced to find responsibility and grow up a little. Mary might be superficial on the surface, but there's something deeper worth exploring.

It's not fair to pick between Jesse (Ethan Hawke) or Céline (Julie Delpy), so we went with both. They just might be the best Gen-X film couple. Audiences couldn't get enough of the pair, so director Richard Linklater made two more movies about them: Before Sunset (2004) and Before Midnight (2013). Traveling was a big part of life for young Gen-Xers, but one didn't need such an experience to appreciate this great story and the time together these likable characters shared.

What does a recent college graduate of the early 1990s do right out of school? Work at the GAP and continue to have casual sex. That's Vickie (Janeane Garofalo). Sure, she might be a Gen-X, 1990s stereotype, but she's also genuine — especially while awaiting the results of her HIV test. Vickie is relatable when she proclaims the only thing she really learned in college was memorizing her social security number. 

Not all of these Gen-X characters grew up in pleasant surroundings. For Tre' (Cuba Gooding Jr.), it's often a matter of survival on the gang-infested, violent streets of South Central Los Angeles. Thanks to pop Furious (Laurence Fishburne), Tre' has a good head on his shoulders and is one of the great, strong, young Black role models in film history. There are plenty of great performances from this John Singleton classic, but Tre' offers the most positive of the bunch.

Veronica (Winona Ryder) might be a member of the popular "Heathers" clan at Westerburg, but all she wanted was for her high school to be a nice place. Trying to fit in at high school while keeping some semblance of individuality can be brutal for any student, no matter the generation. In the late-1980s and early '90s, it seemed more cutthroat than ever. Now, most students don't team up with a handsome but psychotic rebel to kill off the popular crowd.

The video store jockey and antagonist of Kevin Smith's stellar directorial debut, Randal (Jeff Anderson) is best known for his wisecracks, infatuation with hardcore pōrn, inappropriate language, and hassling pal Dante (more on him later). Randal is also content with his lot in life as an early 20-something doing menial work and looking down on others, most notably the customers of the video store. In a lot of ways, he's a Gen-X icon.

In many ways, Lelaina (Winona Ryder, again) is the poster girl for Gen-X films. She enjoyed a successful college career. She isn't happy paying her dues in her field upon graduation, yet she's still trying to prove her independence. Not to mention, this self-proclaimed "non-practicing virgin" is also struggling to succeed in the game of love. She kind of sums up the culture of college grads from the mid-to-early '90s by saying they're "people who are trying to find their own identity without having any real role models or heroes." 

Janet (Bridget Fonda) is trying to find herself in Seattle. She's currently working in a coffee house while figuring out life and what she can do to please her spacey boyfriend, Cliff, who tends to take her for granted. Janet has her insecurities and but she also strives for simple things. Like a guy who says "Bless You" when she sneezes. Doesn't seem too much to ask.

Wayne (Mike Myers) and Garth (Dana Carvery) are not slackers. In fact, they are pretty ambitious, considering their cable-access television show is hit with the locals from Aurora, Ill. Plenty of Gen-Xers figured it was better to create their own jobs than work or make money for someone else. Plus, party animals Wayne and Garth already happened to be among the most iconic characters in the history of Saturday Night Live. 

This is truly John Cusack's greatest role: the ultimate social underdog, Lloyd Dobler. He's an underachieving recent high school graduate with no real direction (also known as a "champion of mediocrity"). But he sets his mind on asking out the most beautiful and intelligent girl (Ione Skye) in his class. Lloyd is actually a very good boyfriend, in addition to a well-liked, loyal friend to all. With that, he's found his calling, showing that the everyman has a chance for greatness no matter how unlikely the scenario seems. 

Yes, we know Dante "wasn't even supposed to be here today." But there's something deeper to the 22-year-old than his doom-and-gloom outlook on life. Dante (Brian O'Halloran), like a good number of 22-year-olds, is afraid of change. He isn't patient, or perhaps confident, enough to apply himself and get a better job than working the counter at a New Jersey convenience store. Also, he'd rather subject himself to the emotional pain inflicted by an ex-girlfriend (Caitlin) than move forward with his devoted current significant other (Veronica). 

Also known as "The Criminal" among the five students subjected to Saturday detention at Shermer High. He's the token bad boy/rebel, but as we see throughout this John Hughes coming-of-age classic, there is a softer side to Mr. Bender (Judd Nelson). The wise-cracking troublemaker has something about him that attracts people, even if they initially can't stand him. Bender is more intelligent than he appears and pretty funny. He's the bad egg Gen-X boys admired, and good girls wanted to date to anger their parents.