The Top Movies About High School From the Past Twenty-Five Years

February 11, 2020 · CLASSMATES FUN

Watching movies about high school often bring back your own memories of that era. True, they’re not always accurate (the characters never have a bad hair day! Or braces! And they always have such perfect style!), but they can still be entertaining. From ridiculously funny to soul-crushingly realistic, here are some of the top high school movies from the 1990’s and beyond.

Clueless (1995)
Rated PG-13

Clueless is a modern-day twist on Jane Austen’s novel Emma, with plenty of added ‘90s lingo thrown in (As if! Whatever!). Our protagonist is charismatic, popular 16-year-old Cher Horowitz (played by Alicia Silverstone), who’s the daughter of a wealthy Beverly Hills lawyer (“the scary kind”, she says). When a girl new to town (Tai, played by Brittany Murphy) starts at their school, Cher and her best friend Dion (Stacey Dash) decide to take her under their wing to boost her popularity. A young Paul Rudd plays Cher’s ex-stepbrother Josh, who’s in college studying to be a lawyer and is, to the annoyance of Cher, always hanging around the house (mostly to seek mentorship from her dad and to help with his cases). Even though parts of the movie have aged (like the large flip phones, pagers, and ‘90s clothing), the story remains entertaining, regardless of how many years have passed.

10 Things I Hate About You (1999)
Rated PG-13

Based on Shakespeare’s Taming of the Shrew, 10 Things I Hate About You follows sisters Kat (Julia Stiles) and Bianca Stratford (Larisa Oleynik), who live in Seattle with their overprotective single father. When new kid Cameron (Joseph Gordon-Levitt) sees Bianca at school, he instantly falls for her, but she isn’t allowed to date unless Kat does. Kat is ill-tempered and has no interest in going out, but Cameron and Bianca devise a plan to pay outcast Patrick (Heath Ledger, in one of his earliest movies) to win her over. All the characters are charming, but it’s the desperately unhip but lovable father who stands out, especially when he delivers lines like “I’m down, I’ve got the 411” and “my momma didn’t raise no fool!”

Romy and Michele’s High School Reunion (1997)
Rated R

Although not technically a movie about high school, this comedy makes the list because it’s about a high school reunion. Best friends Romy (Mira Sorvino) and Michele (Lisa Kudrow) are ten years out of school and living in Los Angeles. Their reunion is coming up, but Romy is worried their lives aren’t exciting enough to show off to the “A Group” (the popular clique), who they desperately want to make jealous. Romy works at a car dealership and Michele is unemployed, and after trying unsuccessfully to find better jobs, they decide to fake it. They buy business clothes, rent a luxurious car, and head on their way, ready to tell everyone the story about how they made millions by “inventing post-its”. It’s hard to admit, but we all feel a little catty sometimes, making this story instantly relatable.

Mean Girls (2004)
Rated PG-13

Written by Saturday Night Live alum Tina Fey and based on the book Queen Bees and Wannabees by Rosalind Wiseman, Mean Girls follows former home-schooler Cady Heron (Lindsay Lohan, in one of her best roles), as she navigates public high school for the first time. She becomes friends with the popular girls (known as “the Plastics”) while secretly trying to sabotage the “Queen Bee” Regina George (Rachel McAdams) for stealing the guy that she has a crush on. But as she learns more about the inner workings of the “in” crowd, she struggles to stay away from the girl drama and become a “plastic” herself. Over 15 years later, people are still quoting the movie. It guest stars other SNL alums Amy Poehler (Regina George’s mom), Tim Meadows (the school principal), and Ana Gasteyer (Cady’s mom). Tina Fey plays Cady’s math teacher.

Lady Bird (2017)
Rated R

This is not a typical high school movie, but instead a movie about a typical high school. Lady Bird follows Christine “Lady Bird” McPherson (Saoirse Ronan), who is a senior living in Sacramento and attends a catholic high school. Lady Bird has dreams to go to the East Coast for college, far away from her parents and the mandatory church services. However, her grades aren’t very good and her parents don’t have the money to send her there, as her dad has just lost his job. Lady Bird and her mother (Laurie Metcalf) have a strained relationship and constantly butt heads, mostly because, as her dad says, they “both have strong personalities”. The movie doesn’t follow a specific storyline and instead focuses on Lady Bird’s life in general, both at school and at home. Although still humorous, there are a lot of dramatic moments, making this film more realistic than other ones about high school.

Booksmart (2019)
Rated R

Booksmart, directed by actress Olivia Wilde in her directorial debut, features two graduating high school seniors, Amy (Kaitlyn Dever) and Molly (Beanie Feldstein), who are best friends but loners. Molly spent the entirety of high school studying in order to go to a prestigious college, and she looks down on her peers for being slackers and partiers. As school is winding down, she finds out that they were in fact able to party on weekends and still get good grades in their classes. It didn’t occur to Molly that you could do both, and she wants to catch up with her peers before school is out. She convinces Amy to go to a party with her the night before graduation so that they can cram four years of rebellion in one night. Lisa Kudrow and Will Forte play Amy’s parents, and Saturday Night Live alum (and Olivia Wilde’s husband) Jason Sudeikis plays the school principal. With raunchy humor and laugh-out-loud scenes, Booksmart is perfect for a casual movie night.

Superbad (2007)
Rated R

Written by actor Seth Rogen and his writing partner Evan Goldberg, Superbad follows two high school seniors Seth (Jonah Hill) and Evan (Michael Cera), who are looking to sleep with the two girls they have crushes on in order gain experience before they leave for college. Although that concept seems like other typical high school films with tired story lines, this actually focuses more on the friendship between the two protagonists. The girl that Seth is interested in, Jules (Emma Stone), invites him to her party and asks him to bring alcohol, and Seth persuades Evan to come with him in order to hit on Becca, the girl he in turn likes. The majority of the film is about their misadventures trying to secure booze for the party, with help from their frenemy Fogell (Christopher Mintz-Plasse in his first role), who purchases a fake ID (he chooses the name McLovin’ as his alias, to the horror of Seth and Evan). Although still a raunchy film, there are sweet moments, and the heart of it all is about friends preparing to go their separate ways before the start of college.

Rushmore (1998)
Rated R

From the quirky mind of Wes Anderson (The Royal Tenenbaums, Fantastic Mr. Fox) and actor Owen Wilson, Rushmore is about an eccentric student named Max Fischer (Jason Schwartzman), who falls for elementary school teacher Rosemary Cross (an unrequited love, of course). He befriends parent Herman Blume (Bill Murray), but Herman also falls for Rosemary, and the two begin dating. When Max finds out, he seeks revenge, playing various damaging pranks on him. This film deals with issues outside of school, but it still shows the life of a teenager and his relationship with his teachers and peers. Wes Anderson is known for his dark comedy, and this definitely falls into that category.

Election (1999)
Rated R

Election is about – what else – a high school election for class president. Reese Witherspoon stars as Tracy Flick and Matthew Broderick plays her teacher, Jim McAllister. Tracy is over-achieving to the point of being irritating, and Jim, who runs the student government, seeks to sabotage the election results so that he doesn’t have to work with her. Although she is annoying, he mostly loathes her because she had an affair with his friend and fellow teacher, which disgusts him. He sees her seductive side and is afraid to be too involved with her. Election is uncomfortable to watch, which is also the reason why it’s so appealing. Although it’s easy to relate to the drama of running for student body president, the film takes it to uncharted territory. It’s definitely worth a watch.

BONUS: Freaks and Geeks (1999-2000)

Although this is a television show and not a movie, it’s included in this list because it’s one of the most realistic representations of high school that’s out there. Although it only ran for one season, it’s since become a cult classic and gave rise to many now-famous movie stars like James Franco, Seth Rogen, Jason Segel, and Martin Starr. The show focuses on two different social groups within a suburban Michigan high school in 1980 – the burnouts who often skip class (the freaks), and the nerds who are socially awkward and are often bullied (the geeks). Lindsay Weir (Linda Cardenelli) is a mathlete who comes from a middle-class family, but she longs to fit in with the burnouts (for reasons her parents and mathlete friends fail to understand), and her younger brother Sam (John Francis Daley) is a freshman who, along with his best friends Neal (Samm Levine) and Bill (Martin Starr), struggles to navigate the ins and outs of high school. There are hysterically funny moments in the show, but for every humorous scene, there are just as many painful ones, which is also true of high school.


Have you seen any of these films or have other suggestions for movie night? Leave a comment below!