Top 20 Best Teen Movies of the 1990s

“Drive Me Crazy” is a 1999 film starring Melissa Joan Hart and Adrian Grenier as high schoolers who decide to start dating as a way to make the people they actually like jealous. But guess what? The more time they spend together they actually end up falling in love with each other. And although they can’t admit it at first, in the end they come together happily ever after. Sure, there’s nothing super original going on here. But sometimes, we want our teen movies to provide comfort rather than total originality. Give us characters we care about, a few laughs and tears, and we’re happy. “Drive Me Crazy” certainly made many of us ‘90s teens happy.

“Cry-Baby” could’ve been a pretty standard 1950s-esque teen romance musical with cool kids, hot cars and greased hair. But, in the hands of the great John Waters it was a smart, over-the-top parody of those exact films. While it didn’t do much business upon its release in 1990, it has since gained recognition for the joyful campiness that Waters is so darn good at. Throw in a young Johnny Depp not afraid to poke fun at his own teen idol image and you have one of the best teen movies of the ‘90s.

“Pleasantville” is a film about a brother and sister living in 1998 who are transported back in time to the world of the ‘50s black and white television show, “Pleasantville”. While there, they see both the good and the bad of a world that isn’t as perfect as it looked on TV. The film is a high school drama, a love story, a social and political commentary and also a pretty cool visual experience that all work together to make one of the truly underappreciated films of the decade. With four out of four stars from Roger Ebert and an 86% rating on Rotten Tomatoes, “Pleasantville” found plenty of critical acclaim even though its showing at the box office was disappointing.

“Drop Dead Gorgeous” is another ‘90s teen movie that has seen a growth in appreciation over time. Despite the impressive cast - which includes the likes of Kirsten Dunst, Brittany Murphy, Allison Janney and Amy Adams - this darkly comic satirical mockumentary about a small town beauty pageant was a box office flop. The film also seemed to split the critics down the middle. However, in the decades since its release, more and more people have discovered “Drop Dead Gorgeous” and it has continued to acquire cult status among teen movie fans.

Wes Anderson proved that he could make a good movie with his directorial debut, “Bottle Rocket”. But, in 1998, his sophomore effort, “Rushmore”, showed the world that he could make a great film. The movie is funny, quirky, completely original, features brilliant performances from Jason Schwartzman and Bill Murray, and is replete with all that now-iconic Wes Anderson visual style. Along with its 90% score on Rotten Tomatoes, the movie has appeared on many ‘best’ lists, including placing 9th on both The A.V. Club and Paste’s best films of the decade.

“But I'm a Cheerleader” is a satirical teen rom-com about a girl who is sent to a conversion therapy camp by her parents in an attempt to change her sexual orientation. That’s probably all we have to say for you to understand why the film was maybe just a little controversial back in 1999. While some critics thought it too broad to really land its satirical shots, views have changed about the movie since its initial run. Even the culture website AfterEllen, which had been hard on the movie in their first review, later came to call it “one of the five best lesbian movies ever made”.

This excellent dark comedy stars Matthew Broderick as a high school teacher who attempts to sabotage the student presidential election of a student he dislikes, played by Reese Witherspoon. The film hits some beautiful satirical notes regarding politics and high school, and features great performances from both Broderick and Witherspoon - the latter of which was deemed one of the “100 Greatest Film Performances of All Time” by Premiere magazine. The movie took home multiple Independent Spirit Awards, including best feature film and best direction. It also picked up an adapted screenplay nomination from the Oscars. “Election” definitely gets our vote.

“The Virgin Suicides” is a movie, Entertainment Weekly in 2015 ranked it the 39th best high school movie ever - which isn’t too shabby! The film was Sofia Coppola’s directorial debut and is focused on the lives of five girls who, after one of them attempts to take their own life, are put under close watch by their religious parents. The film has a much darker tone then many teen movies and is certainly not an “easy” watch. But Coppola tells the story with such a deft hand you wouldn’t know she’d never directed a feature film before.

A dark comedy about a group of three popular high school girls who accidentally kill the fourth member of their clique, “Jawbreaker” had a hard time finding an audience back in 1999. The critics were also unkind to the movie as evidenced by the brutal 14% on Rotten Tomatoes. Much of the criticism revolved around the movie’s similarities to one of the great teen flicks of the ‘80s: “Heathers”. Some reviews even went as far as to deem it plagiarism. However, in the decades since its release, the former has been able to distinguish itself from the latter and be appreciated for the film it is - which, according to Vice, is a “teen classic”.

An iconic raunchy comedy, “American Pie” captures the quintessential emotions of being a teenager, and is the movie that made some of our favorite actors, like Jason Biggs and Alyson Hannigan famous. Like many movies that followed over the years, it imagines that the most important pursuit for teenage boys is the loss of their virginity. So when four friends make a pact to have sex by prom night, we know that it’s going to be hilarious, whether they succeed or not. Along the way they start to figure out who they are and what’s really important to them, so we’re left with a movie that’s one of the greatest teen comedies of the ‘90s.

Everyone remembers their last year of high school. For some of us it’s the best of times, for others, it’s the worst. But the one thing that’s certain is that we never forget it. For a bunch of teenagers, the last night of school is an event to remember. It’s an alcohol-fuelled fiesta with everyone trying to get in their last hurrah. For most of the teens, it’s about going out with a bang, but we’ll never forget that among it all, Jennifer Love Hewitt made us believe in love again. But the best part? Seeing how young and baby faced this star studded cast looks!

Alongside “I Know What You Did Last Summer”, this movie is now a staple in the 90s horror movie canon. As if high school isn’t bad enough, teenager Sidney Prescott has to deal with the terror of a killer targeting her and her friends. Introducing the now famous Ghostface, this movie gave us an icon we now see parading around every Halloween. From the brief appearance of Drew Barrymore to the chilling climax, this movie never fails to keep us enthralled. It took a bunch of teens who love horror movies, and put them inside of one, to point out the cliches even as each character fell right into them.

The ‘90s were filled with the dark and the occult. The second movie on this list with Neve Campbell in the credits, “The Craft” takes us into the world of teenage witchcraft, where newcomer Sarah falls in with a group of outcast girls. All she wants is new friends, but things turn sour when Sarah realizes that the group might be using their magical powers for evil. Starting out as a thriller with a sense of humor, the movie drops all of the comedy to become one of the darkest teenage movies we’ve ever seen.

With prom just around the corner, Zack has to rekindle his popularity after his popular girlfriend leaves him for a reality TV star. Claiming that any girl can replace his ex, Zack is challenged to turn dorky art student Laney into the Prom Queen. What Zack doesn’t expect is that he and all his friends will come to like Laney. This movie has plenty of fun in it, like the iconic makeover scene, and also some heartbreaking scenes like when Laney finds out about the bet. It’s not the most conventional start to a relationship, but in our heart of hearts, we all knew that Zack and Laney were meant to be.

Schools and educators have been trying to get teens interested in Shakespeare for decades - if not longer. Turns out, the way to do it is to make an amazing “Romeo and Juliet” movie. While there have been some good ones in the past, they don’t come close to matching the vibrancy, passion and visual aesthetic of Baz Luhrmann’s modern pop take on the century’s old play. Grossing over $145 million at the box office, scoring 73% on Rotten Tomatoes and an A- audience CinemaScore, 1996’s “Romeo + Juliet” made Shakespeare actually kind of cool.

Widely known as one of Quentin Tarantino’s favorite films, this movie follows a rag tag bunch of teenagers celebrating the last day of school. There’s something charming about this movie that reminds us of our own teenage days. Whether it’s the humiliating hazing, our first keg party, or those alternating undertones of excitement and vague boredom that permeate the movie, we can all relate to one of the things these crazy kids get up to. It’s a coming of age story that leaves us feeling a little nostalgic, and we can’t help but be grateful that the spirit of adolescence can be captured so well on film.

Most people know Sarah Michelle Gellar as Buffy, the ass kicking vampire slayer, but in this movie she transforms from righteous do-gooder into Kathryn Merteuil, the beautiful but twisted teenager who treats manipulation like a sport. Egging on her playboy stepbrother, played by Ryan Phillippe, the two of them start upon a path of destruction that leaves people damaged and distraught in their wake. This is one of the darkest teen movies we’ve ever seen, and thanks to the incredible performances of the cast, also one of the best.

It’s hard to believe that Drew Barrymore could ever be anything other than radiant, but this movie shows us that she can also be pretty dorky. Playing Josie, a journalist, she goes undercover as a high school student for research, and is forced to relive some of the worst days of her life. Lucky for her, she has a second chance to reinvent herself. Just like her entire office who watch via a hidden camera, we can’t look away when Josie becomes one of the popular kids, or gets voted Prom Queen. And there’s nothing like the tension in that final scene when we wait to see whether Josie will ever get her first kiss.

If you miss Heath Ledger as much as we do, you’ll know that his role as heartthrob Patrick is one of his best. Based on Shakespeare’s “The Taming of the Shrew”, this teen rom-com sees two very different sisters try to manage their time in high school. Popular Bianca wants to date and party, while her sister Kat wants to stay at home and read feminist literature, but Bianca can’t date until Kat does. And if there’s one movie scene we all dream of re-enacting in our lives, it’s the one where Patrick serenades Kat with the help of the marching band.

Alicia Silverstone steals the show in this cult classic as Cher Horowitz, a Valley girl with more to her than meets the eye. Playing the ditzy teenage daughter of a successful lawyer, she thinks she can argue her way out of any situation. She ends up adopting new girl Tai, and puts her on the path to popularity. This comes with pitfalls once Tai becomes more popular than her, and decides she wants to date Cher’s step brother Josh. Horrified by this, Cher realizes that she herself is in love with Josh, despite their differences. With great fashion, good natured matchmaking, and true love, as if this movie could be anything but brilliant!