4 Amazing ’90s Movies That Perfectly Capture The Millennial Teenage Experience

Being a Millennial in the late ’90s was a whirlwind of emotions. Limited Internet access and no mobile phones made navigating high school a very different experience from today’s norms. If you wanted to make plans, you’d have to call a friend’s house and probably talk to their parents first. Relationship dynamics played out in real time instead of being broadcast over social media. But that doesn’t mean it was any less intense.

Notes passed via random kids in class were the closest thing to social media. Rumors spread through whispers and in gossip columns of school newspapers. Popular kids ruled the school, and everyone else faded into the background. Whether you lived it or would like to know what it was like, there are several movies that capture the ’90s teenage experience. There’s a story about a prom bet, a tale of unrequited love, a jealousy scheme gone wrong, and a film about a cynical girl who falls for a bad boy. 

She’s All That (1999)

She’s All That focuses on the high school social hierarchy. The story begins when Zack Siler (Freddie Prinze Jr.) finds out that his girlfriend cheated on him with a Reality TV star. He brushes off their breakup, claiming that he can make any girl in the school popular just by dating her. When his friend Dean (Paul Walker) disagrees, they make a bet in which Zack has to turn a random girl from school into the prom queen in just six weeks. Unsuspecting art student Laney Boggs is chosen for the bet.

Zack gets to work by trying to be friends with Laney (Rachael Leigh Cook). She initially brushes him off until he asks for help with art class. Laney does her best to ignore his charms. But Zack uses (what starts out as) fake sincerity to win her and her family over. He even gets his sister to give Laney a makeover, which brings out her natural beauty and helps with her shyness. Things get complicated when Zack really starts to fall for Laney, which upsets Dean and makes his ex-girlfriend super jealous.

Can’t Hardly Wait (1998)

Can’t Hardly Wait places the time-old tale of unrequited love in a high school setting. The story chronicles the events of a graduation party where Preston Meyers plans to tell his secret crush, Amanda Beckett, how he feels about her. Amanda, who is newly single after being dumped by her boyfriend, wanders around the party alone while fending off various male suitors. Over the course of the evening, their advances slowly start to agitate her. 

Meanwhile, Preston (Ethan Embry) spends most of the night working up the courage to give Amanda (Jennifer Love Hewitt) a letter in which he explains why they would be the perfect couple. Due to several distractions, he loses the letter, and it eventually ends up in Amanda’s hands. Moved by the words, she decides to find Preston even though she has no idea who he is or what he looks like. When they finally meet, things don’t go the way Preston had hoped. 

10 Things I Hate About You (1999)

While the Shakespeare play on which 10 Things About You is based is very misogynistic, the film is pretty harmless. The story focuses on Katrina (Julia Stiles) and Bianca Stratford (Larisa Oleynik), who are constantly at odds with their overprotective father, Walter. Each sister has aspirations that their dad disapproves of. Kat wants to go to college in New York, and Bianca wants to date. Frustrated by his daughters, Walter gives in and says Bianca can only date if Kat does. 

Knowing that Kat’s standoffish personality will make dating difficult, Bianca and her friends decide to pay bad boy Patrick Verona (Heath Ledger) to date her. Patrick does his best to win Kat over, and his charm eventually works. But when Patrick asks her to the prom, knowing that she doesn’t believe in the tradition, she becomes suspicious. Everything falls apart at the prom when Bianca and her date get into a fight, leaving Kat caught in the middle of the drama. 

Drive Me Crazy (1999)

Drive Me Crazy is a story about finding love where you’d least expect. Like most teen movies of the ’90s, it begins when the popular Nicole Maris (Melissa Joan Hart) decides to team up with rebel Chase Hammond (Adrian Grenier), to make their respective crushes jealous. The pairing isn’t too random since Nicole and Chase live next door to each other and used to be childhood friends. But they eventually drifted apart after Chase went through a family tragedy and their interests changed.

Despite some initial hiccups in their scheme, which includes a clause that allows either of them to ditch at any time, plan goes really well. However, things are never straightforward when feelings are faked. The arrangement starts to get messy when their friends get involved, with Chase accusing Nicole of being selfish. Friendships are tested, and real feelings are exposed when the pair finally gets what they want.