When John Hughes hung up his hat as the resident teen film storyteller, the world was left to wonder if we would ever experience the same coming of age stories again. Luckily, the ’90s proved to be a decade where teen films came in abundance, but that didn’t guarantee a steal at the box office. Nor did it promise that teens of the ’90s would connect to the stories adults continued to assume were about them. Still, as the decade wore on, several films about teenage life, and more specifically high school, were born. Some were tender and earnest, while others were seemingly funny and often ridiculous, but they were relatable above all else.
In the spirit of this nostalgic journey, we’ve rounded up 10 teen classics from the era that defined the genre and teenage life in the ’90s, for better or worse.

She’s All That, 1999
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.”
Dazed and Confused, 1993
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.
American Pie, 1999
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.
Clueless, 1995
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.
Never Been Kissed, 1999
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.
10 Things I Hate About You, 1999
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.
But I’m a Cheerleader, 1999
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.
Drive Me Crazy, 1999
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.
Can’t Hardly Wait, 1998
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.