The start of September is forever associated with back to school. Every year as we approach the 1st of the month, I go back to that first day of class feeling. Though I am not sitting through 8 hour days of lectures, I do miss the classroom friendships and lunchtime chats about student life. One of my favorite rituals for this time of year is to rewatch old movies that are set in a back-to-school plot. It’s like watching holiday movies around Christmas but make it academic. While there are some high school memories I’d rather forget—aka my yearbook photos—the sense of nostalgia never gets old. My mind goes to Cher strutting around Beverly Hills in her perfectly plaid outfits in Clueless or Channing Tatum trying to pass off as a college student in 22 Jumpstreet. I highly recommend taking a movie night or two to revisit these back-to-school classics.
I can’t think of Clueless without thinking of plaid and to this day, I’ve never seen anyone pull off a plaid blazer and mini skirt set quite like Cher Horowitz. In the opening scene, Cher walks into a closet bigger than my bedroom and picks out her clothes on a desktop computer. Relatable! So were the outfits she wore to school, skirt and strap regulations, anyone? If I sound jealous, it’s because I was watching Alicia Silverstone and Stacey Dash give Brittany Murphy a makeover and live their best teenage lives. The three girls navigate report cards, debate class, parties in the Valley, and teenage love in this ‘90s classic.
She’s The Man (2006)
This movie is prime Amanda Bynes cinema and the modern adaptation of Shakespeare’s Twelfth Night. It reminds me of the teenage brother and sister version of the Parent Trap but instead of swapping parents, Amanda Byne’s character, Viola pretends to be her brother at his new boarding school. Saying the plot was complicated would be an understatement, there’s a love hectagon between all the characters that needs a handwritten map with arrows to follow. The varsity soccer team, school uniforms, and boarding school setting are sure to give you pangs of nostalgia.
22 Jump Street (2014)
Truly one of the funniest comedies I’ve seen thanks to Channing Tatum and Jonah Hill as they play cops going undercover at a local college. Also, one of the few sequels that didn’t flop (21 Jump Street is the high school version). Schmidt and Jenko awkwardly try to fit in with college students and experience all the classic firsts—living in dorms, frat parties, and spring break. While searching for the supplier of a synthetic drug circling campus, Schmidt and Jenko realize that even though they’re not really college students, they have some growing up to do. But don’t worry there are way more laughs than Hallmark moments.
Lady Bird (2017)
Would you like some teenage angst with your high school experience? Because that’s what Saoirse Ronan is serving in the coming-of-age drama Lady Bird. It’s the quintessential outsider movie as the main character Christine, who calls herself “Lady Bird”, dreams of escaping her Catholic high school and small town for adventure. There are mother/daughter issues, first romance, senior year of high school, and college applications. All relatable growing pains as you transition from a teenager to an adult but with more seriousness than the comedies on this list.
Confessions of a Teenage Drama Queen (2004)
Emphasis on the drama queen, this movie is a Lindsay Lohan musical comedy, and a 2000s nostalgia trip in one. The main character, Lola, is forced to move from New York City to suburbia by her mother and she isn’t happy about it. Classic teenage movie. She starts at a new high school and snags the lead in the school’s musical. She shamelessly sings, dresses like a bohemian celebrity, and sneaks into rock concerts. I will forever rewatch this movie for the rebelliousness, Juicy Couture sweatsuits, hallway showdowns, and Megan Fox cameo.
A pack of quintessential teenage boys tries to live out their high school dreams of parties and girls before graduation. Superbad follows high schoolers Seth and Evan, played by Jonah Hill and Michael Cera, as they awkwardly try to secure alcohol for their crushes and make it to a party. The plot was written by Seth Rogan and Evan Goldberg, loosely based on their Grade 12 experience during the ‘90s. The movie perfectly captures how high school was depicted in pop culture before the TikTok era of Gen Z.
Bring It On (2000)
Before Netflix’s Cheer Squad there was Bring It On that inspired cheerleading dreams for high schoolers everywhere. It was the first of five sequels and arguably the best of the series becoming a cult classic. Kirsten Dunst stars as Torrance, the newly elected team captain of her high school cheerleading squad who discovers the team’s routines are plagiarised from another squad. With the help of a sassy gymnast, Missy, Torrence tries to save her team before the Daytona Beach Nationals. There’s hairspray, sports games, 2000s music, and lots of scenes in a high school gymnasium.
Bookworms Amy and Molly, played by Kaitlyn Denver and Beanie Feldstein, spent most of their high school years focusing on grades, not parties. They experience FOMO when they realize they missed out on underage drinking, dating, and rule-breaking—you know the usual teenage antics. Some teenagers aim for Yale, and others aim for an impressive alcohol tolerance before college. Same same but different. It’s almost like the female version of Superbad watching Amy and Molly try to fit as much debauchery as possible in a night.
Like what you saw? Here’s more:
The ’90s & 2000s Shows That Guided Me Through Teenagehood
The Best Movie Soundtracks By The Decade
Nostalgic Movies That Made Us Want To Start A Band