Movies to Watch if You Love ‘10 Things I Hate About You’

The 1990s (and arguably the early 2000s) were such a simpler era. A decade before WiFi turned our coffee shops into silent offices and a cloud was simply that fluffy thing in the sky. Moreover, it was when the 1999 film 10 Things I Hate About You gave us Heath Ledger’s impromptu performance of “Can’t Take My Eyes Off You,” which has become ingrained in pop culture. 10 Things I Hate About You is a contemporary retelling of William Shakespeare’s classic play The Taming of the Shrew, set at a modern American high school. Gil Junger’s direction expertly blends the playwright’s timeless wit with the comedic and emotional intricacies of teenage life. 

The film stars Julia Stiles, the late Heath Ledger, Joseph Gordon-Levitt, and Larisa Oleynik, and combines Shakespearean origins and 90s teen culture, making it a cult classic. So, if you’re seeking more flicks like 10 Things I Hate About You, here is a delightful selection of films that will whisk you away on a nostalgic journey back to those glorious (or not) teenage years. 

Clueless (1995)

Clueless, directed by Amy Heckerling, is a classic teen comedy that perfectly captures the spirit of 1990s American teenage culture. The film is set in the sun-drenched environs of Beverly Hills and revolves around Cher Horowitz, a fashion-savvy, self-proclaimed matchmaker played endearingly by Alicia Silverstone. Clueless, loosely based on Jane Austen’s Emma, depicts Cher’s struggles navigating the nuances of high school society while playing cupid for her classmates and teachers, often with comically unforeseen consequences.

Never Been Kissed (1999)

In Never Been Kissed, a Raja Gosnell-directed romantic comedy, Drew Barrymore plays Josie Geller, whose story is both touching and hilarious. Aspiring writer and the Chicago Sun-Times’ youngest copy editor, Josie is tasked with a difficult assignment: posing as a high school student and writing about the modern youth culture. But now that she’s back, Josie has to deal with the painful memories of her high school years, when she was the target of bullying because of her awkwardness and lack of social skills. She struggles with unresolved emotions and hopes for forgiveness as she navigates teenage drama, love triangles, and prom demands. 

She’s All That (1999)

If you’re in the mood for a flick that combines teenage romance, high school drama, and a sprinkle of prom night chaos, then She’s All That is the movie you’ll want to hit the replay button on. Directed by the talented Robert Iscove, this film dives headfirst into the timeless dilemma of seeing beyond surface-level beauty. The story follows Freddie Prinze Jr.’s Zack Siler, a successful high school athlete who, after his fiancée dumps him, wagers to transform Rachael Leigh Cook’s artsy and shy Laney Boggs into the prom queen. 

4Mean Girls (2004)

In Mean Girls, Tina Fey and company combine biting humor and insightful commentary to explore the turbulent world of high school social politics. The film, directed by Mark Waters, written by Tina Fey, and based on Rosalind Wiseman’s self-help book Queen Bees and Wannabes, follows Lindsay Lohan’s character, Cady Heron, as she adjusts to American high school life after having been homeschooled in Africa. She soon encounters ‘The Plastics’—a trio of popular girls led by the formidable Regina George. Mean Girls has effortlessly cemented itself as a must-watch in pop culture. 

Drive Me Crazy (1999)

John Schultz’s Drive Me Crazy takes you through the complicated web of teenage love, complex friendships, and the never-ending pursuit of fitting in. Nicole Maris, played by Melissa Joan Hart, and her neighbor, the rebellious Chase Hammond, portrayed by Adrian Grenier, are at the center of the story. Both jilted by their crushes, they hatch a plan to pretend to date each other, hoping to make their desired partners jealous and regain their social status. The classic “fake relationship” trope evolves into genuine feelings. The film, titled after Britney Spears’s song, “(You Drive Me) Crazy,” perfectly captures the spirit of late ’90s high school life.

Bring It On (2000)

A cult classic and pop culture touchstone, Bring It On cheers its way into discussions on race, integrity, and spirited rivalry. The film vaults into the fiercely competitive world of high school cheerleading with intense enthusiasm and commentary on cultural appropriation. At the heart of the story is Torrance Shipman, played by Kirsten Dunst, who takes the lead as the captain of the Rancho Carne Toros cheerleading squad, only to discover their award-winning routines were stolen from the East Compton Clovers, an underfunded yet talented team led by the formidable Isis, portrayed by Gabrielle Union. 

Easy A (2010)

In his 2010 film Easy A, director Will Gluck gives Nathaniel Hawthorne’s The Scarlet Letter a fresh, contemporary spin by placing the story in the dramatic world of American high schools. Emma Stone’s portrayal of Olive Penderghast, a bright and funny teenager, is spot on, and the film follows her as she navigates the dangerous seas of high school rumors. Olive adopts a scandalous new reputation once a tiny white lie about losing her virginity spins out of control. As the allegations spread, she wears a scarlet ‘A’ on her clothes, embracing her newfound celebrity while criticizing the double standards and hypocrisy surrounding female sexuality.

But I’m a Cheerleader (1999)

The sarcastic and bold But I’m a Cheerleader, directed by Jamie Babbit, examines gender roles, sexuality, and the pressures of modern society. Natasha Lyonne gives a powerful performance as Megan Bloomfield, a stereotypical high school cheerleader, who is taken to “True Directions,” a conversion therapy camp because her family and friends think she’s a lesbian. Megan struggles with her sexual orientation amid the strange, pastel environment of the center that aims to “cure” young people of their homosexuality. As she meets a range of characters confronting similar challenges, especially the rebellious Graham, played by Clea DuVall, Megan discovers authentic love and acceptance. 

Save the Last Dance (2001)

Save the Last Dance melds the allure of dance with the raw complexities of urban life and racial dynamics. Directed by Thomas Carter, The film follows Sara, a white ballet dancer played by Julia Stiles, whose ambitions are shattered by the loss of her mother. After moving to Chicago, she enrolls in a predominantly Black high school, where she meets Derek, portrayed by Sean Patrick Thomas. Derek introduces her to the vibrant hip-hop dance world, and their shared passion soon sparks a romantic relationship. However, their interracial romance confronts societal prejudices, familial expectations, and personal aspirations.

(Featured image: Touchstone Pictures)

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Faith Katunga

Faith is a freelance journalist with an insatiable curiosity for all aspects of current events, from the global economy and fashion to pop culture and travel. She watches an absurd number of cat videos on Instagram when not reading or writing about what is going on in the world. Faith has written for several publications, including We Got This Covered, Italy Magazine, TheTravel, etc., and holds a master's degree in Fashion Culture and Management.