Every Movie That Defined Your Teenage Life in the ’90s

After his girlfriend breaks up with him for The Real World star Brock Hudson (Matthew Lillard), Zack Siler’s (Freddie Prinze Jr.) reputation takes a hit, but his ego remains when he claims he can still have any girl in the school. This prompts his supposed best friend Dean (played by the late Paul Walker) to wager a bet that suggests Zack can’t turn just any girl into the prom queen in six weeks. What follows is the classic teen film trope where the popular guy tries to convert a not-so-popular girl to his side of the tracks, and to the surprise of no one — they fall for each other. Then, of course, the dorky girl finds out she’s a bet and gets her heartbroken, only to be swept off her feet again when the cool dude proclaims his love for her in front of the entire school. Years later, the film has been widely criticized for its tone-deaf narrative, but that hasn’t stopped us from rewatching it again and again.

Most memorable moment:

As much as we hate to admit it, the scene where Laney Boggs (Rachel Leigh Cook) reveals her makeover while Kiss Me by Sixpence None the Richer plays in the background is the stuff of teen film glory. It may have taken us several years later to realize how tragic it was to commend a film where a woman was only made to feel beautiful after someone changed how she looked entirely, but that’s the '90s for you.

Why we love it:

She’s All That is saturated with an all-star cast including Freddie Prinze Jr., Rachael Leigh Cook, Matthew Lillard, Paul Walker, Kieran Culkin, Usher, Lil Kim, Gabrielle Union, Clea DuVall, Anna Paquin and two sneaky appearances Sarah Michelle Gellar as the “girl in the cafeteria” and Milo Ventimiglia as “the soccer player.”

On the last day of high school in 1976, a group of teens finds themselves doing what teens do best without adult supervision — smoking weed and drinking beers. The scene is set in Austin, Texas, where star football player Randall "Pink'' Floyd (Jason London) has been forced to sustain from drugs and alcohol if he hopes to win the championship game. Meanwhile, upcoming freshmen try to avoid getting hazed as fellow students stumble upon a keg party where mayhem and hilarity ensue. It may not have made it big at the box office, but the commercial success of Dazed and Confused following its release created a loyal fanbase, and it continues to be a reference point for successful teen films of the ‘90s. It didn’t hurt either that the film was jam-packed with an ensemble cast including Rory Cochrane, Joey Lauren Adams, Milla Jovovich, Jason London, Parker Posey, Adam Goldberg, Ben Affleck, and Matthew McConaughey.

Most memorable moment:

Among the many quotable scenes throughout Dazed and Confused, nothing is more memorable than Matthew McConaughey’s infamously ad-libbed line, “alright, alright, alright.”

Why we love it:

It’s a classic coming of age film that will bring you back to the innocence of being a teenager without the ick factor. The soundtrack is pretty incredible, too.

When five horny pals decide to make a pact that they will have sex before college, you know the laughs are going to come in droves, and that’s precisely what we got with the release of American Pie in 1999. Arguably one of the most blatantly sexual teen films of the '90s, American Pie featured a cast that would go on to become major players in film and television during the 2000s, including Jason Biggs Chris Klein, Natasha Lyonne, Tara Reid, Alyson Hannigan, Sean William Scott, and Mena Suvari. The plot mainly focuses on the best friends getting laid, but there are some genuine moments amidst comedic scenes that feel more now like low-level fart jokes at best. Still, American Pie delivers a story that spoke to many of the true fears high school graduates face like the ending of friendships and the beginning of unknown responsibilities while facing the first stage of pending adulthood. At its core is a heartfelt story that reminds teenagers to seize the moments that matter most and stop placing unnecessary pressure on the things they have little control of, like having sex before college or falling in love with the perfect person.

Most memorable moment:

Let’s just leave it at “warm apple pie.”

Why we love it:

This was the type of film that teens knew was a bit too risqué for their parents to know about, so they sneak into the theatre to see or watched it at a friends house when the adults weren’t around.

If you weren’t walking the halls of your high school responding to everything with “as if!” or “whatever,” then we have to ask — were you even really there? Clueless spawned a new era of slang terms that landed themselves on t-shirts, pens, stickers, and probably those little notes we used to pass back and forth before the digital world took over. In the mid-90s, Cher, Tai, Dionne and the rest of the student body at Bronson Alcott High School became the gold standard for fashion, partying, and flirting. And even though most of us could never dream of living the lavish Beverly Hills lifestyle of Cher Horowitz (Alicia Silverstone), we could likely relate to the average girl stereotypes that Tai Fraiser (played by the late Brittany Murphy) was known for before Cher decided to give her a makeover. Despite some of it’s over the top moments, Clueless was born at a time when the tackiness of the '90s had reached its peak, and it leaned in so well to that moment that going back now feels like you’ve entered a time machine.

Most memorable moment:

Without a doubt the moment when Cher fails her driving test and comes home to a confession from Tai that she has fallen for Cher’s ex-stepbrother, Josh Lucas (Paul Rudd). This sends Cher down a confusing spiral as she lists why Tai and Josh wouldn’t make a good couple because subconsciously, she is in love with him. Tai retaliates with a long-lasting sting: “You’re a virgin who can’t drive.”

Why we love it:

Even though the concept of two ex-step siblings falling for each other is a bit gross, there is nothing like drooling over a young Paul Rudd on the screen.

Josie Geller (Drew Barrymore) may have been a 25-year old aspiring journalist, but when she goes undercover for a story at a local high school, we begin to realize that she never really grew out of her teenage personality. That’s where Josie learns the hard way that bullying and popularity remain synonymous and pretending to be someone you’re not to reach the top never works. Thankfully, Josie discovers the best version of herself, which prompts her to change her undercover assignment to an open letter for her faux classmates where she comes clean about her age and the story she was trying to chase when all the while realizing what she was really chasing was the woman she wants to become. Oh, and she’s fallen in love with her teacher and bravely announces that she’s never been kissed and hopes he will be the one to change all of that.

Most memorable moment:

When she finally gets that kiss on the baseball field in what is probably the most anxiety-inducing lead up to any climax between two lovers in a teen film.

Why we love it:

Because Drew Barrymore is a pro at delivering adorably awkward moments on a level that’s so relatable we could write it ourselves.

The concept of modernizing William Shakespeare's The Taming of the Shrew is not something any teenager of the '90s asked for, but it’s the film we most certainly needed. When Cameron (Joseph Gordon-Levitt) finds out Bianca (Larisa Oleynik) can’t date until her unpopular sister Kat (Julia Stiles) dates, he makes it his mission to find Kat the perfect guy. The only issue is, no guy in school wants to go anywhere near the dark and moody Stratford sister, that is, until Cameron convinces Patrick (Heath Ledger) to date her in exchange for some cold hard cash. Things start off rocky for Patrick and Kat, but he eventually wins the sister’s affection, and they fall in love. Everything seems to be going according to plan until Kat finds out that Patrick is being paid to date her. Naturally, the whole thing blows up in everyone’s face, and the end of the movie hosts an adorable sequence of events where we see Patrick confessing his true feelings for the sister who, as it turns out, isn’t so angry after all.

Most memorable moment:

It’s a toss-up between Heath Ledger’s serenading Julia Stiles character from the bleachers or Kat’s poem where she lists the ten things she hates about Patrick before admitting through tears that she doesn’t hate him; not even close; not even a little bit; not even at all.

Why we love it:

Despite how typical the plot line was for its time, 10 Things I Hate About You has a genuine likability and includes characters that seem wise beyond their years. It also serves as a time capsule before the untimely passing of Heath Ledger.

Any teenager who was questioning their sexuality in the '90s was probably watching But I’m a Cheerleader on repeat thanks to its satirical look at parents who can’t seem to handle their kids coming to terms with their sexual identity. The film follows high school cheerleader Megan Bloomfield (Natasha Lyonne), who is promptly sent to a residential inpatient conversion therapy camp to cure her lesbianism. While there, Megan falls in love and comes to embrace her sexuality instead of fighting it off for her parents' sake. Despite its dark underbelly, But I’m a Cheerleader created an essential narrative between teens and their parents, or at the very least, it created a safe space for teen members of the LGBTQ+ community to own their sexual identity while understanding that that love truly can conquer all — with a few laughs along the way.

Most memorable moment:

The graduation scene where Megan performs a cheer proclaiming her love for Graham, and basically all the other moments when we get to see Natasha Lyonne and Clea DuVall performing next to each other on-screen.

Why we love it:

It’s an important film that doesn’t get nearly enough of the credit it deserves.

Borrowing from the plot line of She’s All That and various other teen flicks of the decade, Drive Me Crazy flips the gender narrative for high school makeovers. Nicole (Melissa Joan Hart) is devastated to learn her crush isn’t interested in her, so she plots to make him jealous by convincing her next-door neighbour, the very unpopular Chase (Adrian Grenier), to let her make him over so he can join her crew. Chase is intrigued by the offer because he knows it will make his ex-girlfriend jealous after recently breaking up with him. But, like most stories that start out this way, Nicole and Chase fall for each other and ultimately begin to learn the true cost of popularity. The storyline might be overplayed and tired, but Drive Me Crazy had a loyal fanship that has grown as the next generation continues to embrace how delightful cheesy it is.

Most memorable moment:

That moment at the centennial dance when Chase asks Nicole to dance with him and she asks him who they are trying to make jealous, and he responds with “Everyone, Nicole. Everyone.”

Why we love it:

We get to witness a young Adrian Grenier well before the fame that followed his starring role in Entourage. The soundtrack also lends itself well to the music of the time featuring covers by popular '90s group The Donnas and well-known hits from Backstreet Boys, Less Than Jake, and Jars of Clay. And how could we forget the cast showing off their acting chops further in the official music video for Britney Spears smash hit Drive Me Crazy.

The year was 1998, and Jennifer Love Hewitt was at the height of her fame, making her the ideal cast for the lead role of Preston Meyers (Ethan Embry) love interest in Can’t Hardly Wait. The film takes place on the last day of high school when Amanda Beckett’s (Jennifer Love Hewitt) jock boyfriend dumps her right before all of their classmates attend a graduation party. Preston sees this as an opportunity to express his undying love for her and come clean about the crush he’s had since the beginning of high school. Against the better judgement of his best friend Denise (Lauren Ambrose), Preston decides to confess to Amanda by hand delivering a love note he wrote for her when they first met. While trying to grab her attention at the party, Preston faces a series of hilarious setbacks. Eventually, the whole plan backfires on him when Amanda puts him (and all the other boys at their school) on blast because they seem only to like her for her beauty instead of her brain. Luckily, this sappy lovebird is able to tell his crush how he really feels before it's too late.

Most memorable moment:

The awkward sexual encounter that’s shared between Kenny (Seth Green) and Denise perfectly captures the embarrassing journey teens often face when attempting to lose their virginity.

Why we love it:

The movie barely takes a moment to catch its breath before leaning into the next funny moment.

Possibly the most scandalous film of our ‘90s teen lives is Cruel Intentions. A modern adaptation of the novel Les Liaisons dangereuses, written by Pierre Choderlos de Laclos in 1782. It follows the lives of some obscenely wealthy and privileged teenagers that use their power as a means of plotting against each other to continue their climb to the top. Kathryn (Sarah Michelle Gellar) creates a wager with her stepbrother Sebastian (Ryan Phillippe) to devirginize a new student, Annette (Reese Witherspoon). If Sebastian fails to seduce Annette, Kathryn will gain possession of his vintage Jaguar XK140. If he succeeds, Kathryn will have sex with him, which may sound like it’s crossing the line for step-siblings, but since Kathryn is the only girl Sebastian hasn't slept with — he sees it as a necessary conquest. The problem occurs when Sebastian falls in love with Annette, creating a once again classic tale of a boy meeting a girl and changing who he is just to be with her. When Kathryn realizes what’s happening her rage takes over and leads to Sebastian's accidental death.

Most memorable moment:

The kiss between Selma Blair and Sarah Michelle Gellar had all of us hot and bothered, regardless of our sexual identity.

Why we love it:

The revenge that Annette plots against Kathryn are a bittersweet symphony of events.