10 Movies and TV Shows Like 10 Things I Hate About You (1999)

Description: Like '10 Things I Hate About You', 'Clueless' is a clever modernization of classic literature (Jane Austen's 'Emma') set in a contemporary high school. Both films feature sharp, satirical takes on teenage life and romance, with strong female protagonists who undergo personal growth. The movies share a similar visual style—bright, fashion-forward aesthetics that defined 90s teen cinema—and both use humor to explore deeper themes of class, identity, and social expectations.

Fact: Alicia Silverstone's character was originally written as a villain. The film popularized several fashion trends, including plaid mini-skirts and knee-high socks. It spawned a TV series and a failed Broadway musical adaptation.

Description: This late-90s ensemble comedy shares with '10 Things I Hate About You' a focus on high school social dynamics during a single transformative night (a party vs. a prom). Both films feature multiple intersecting storylines, witty dialogue, and a nostalgic celebration of teenage experiences. The movies capture similar late-90s aesthetics and music trends, blending comedy with moments of genuine emotional depth about young love and self-discovery.

Fact: The film features early appearances by future stars like Jason Segel and Melissa Joan Hart. Several cast members were actually teenagers during filming. The 'Humanitarian Party' scene was based on real high school parties.

Description: Like '10 Things I Hate About You', 'Never Been Kissed' is a romantic comedy about social outsiders navigating high school culture, with the added twist of an adult protagonist. Both films explore themes of authenticity, popularity, and first love, blending humor with heartfelt moments. They share a similar late-90s visual style and soundtrack aesthetic, and both feature prom as a climactic setting for romantic resolution.

Fact: Drew Barrymore's production company produced the film. The baseball scene required 42 takes. Barrymore insisted on doing her own stunts, including the famous bleacher fall.

Description: Similar to '10 Things I Hate About You', 'She's All That' is a modern teen romantic comedy that reimagines a classic story—in this case, 'Pygmalion'/'My Fair Lady'. Both films feature popular male leads who make a bet to transform an unconventional girl, leading to unexpected romance. The films share themes of high school social hierarchies, personal transformation, and authentic self-discovery. Both were released in 1999, capturing the same late-90s teen movie aesthetic with colorful visuals, witty dialogue, and iconic prom scenes.

Fact: The film's famous 'slow clap' scene was improvised by Freddie Prinze Jr. Rachael Leigh Cook wore minimal makeup to emphasize her character's 'unattractive' transformation. The movie's success helped launch the careers of both Prinze and Cook as teen movie stars.

Description: While focused on cheerleading, 'Bring It On' shares with '10 Things I Hate About You' a sharp, witty take on high school dynamics and female friendships. Both films feature strong female protagonists who challenge the status quo, clever dialogue, and vibrant visual styles that capture youthful energy. The movies balance comedy with thoughtful commentary about competition, authenticity, and teenage social pressures, all set against colorful high school backdrops.

Fact: The cheer routines were performed by real squads. Kirsten Dunst trained for months to play a cheerleader. The film spawned multiple direct-to-video sequels and a Broadway musical.

Description: This modern fairy tale shares with '10 Things I Hate About You' a classic story structure (Cinderella vs. Shakespeare) updated for contemporary teen audiences. Both films feature intelligent, independent female leads who challenge their circumstances, romantic relationships that develop through written communication, and climactic dances that resolve the central conflicts. The movies balance fairy tale romance with realistic teenage concerns and witty dialogue.

Fact: Hilary Duff performed all her own cheerleading stunts. The diner set was built from scratch for the film. Chad Michael Murray's audition impressed producers so much they rewrote his character.

Description: Both 'Mean Girls' and '10 Things I Hate About You' are iconic teen comedies that blend sharp humor with insightful social commentary. They feature intelligent female protagonists who navigate complex high school hierarchies while maintaining their individuality. The films share themes of identity, peer pressure, and the performative nature of teenage life. Like '10 Things', 'Mean Girls' has become a cultural touchstone with endlessly quotable dialogue and memorable characters.

Fact: Lindsay Lohan actually attended high school while filming. The 'Burn Book' was inspired by real-life 'slambooks' from writer Tina Fey's high school. Rachel McAdams was nearly 26 when playing a high school junior.

Description: 'Easy A' shares with '10 Things I Hate About You' a smart, self-aware protagonist who navigates high school social dynamics with wit and intelligence. Both films are modern takes on classic literature (The Scarlet Letter vs. The Taming of the Shrew) and feature strong female leads who challenge stereotypes. The movies balance comedy with thoughtful commentary on reputation, rumors, and teenage sexuality, all while maintaining a bright, energetic visual style.

Fact: Emma Stone ad-libbed many of her character's funniest lines. The film's director intentionally cast older actors as teachers to emphasize the generation gap. The famous 'Pocketful of Sunshine' dance scene was completely improvised.

Description: 'The DUFF' mirrors '10 Things I Hate About You' in its exploration of high school labels and social status. Both films feature unconventional female leads who resist being defined by others, with romantic subplots that develop through witty banter and personal growth. The movies share a similar tone—balancing humor with heartfelt moments—and both ultimately celebrate individuality over conformity. Visual similarities include vibrant high school settings and dynamic party scenes.

Fact: Mae Whitman was 26 when playing a high school senior. The film's director worked closely with the book's author to maintain authenticity. Several scenes were improvised, including much of Whitman's comedic dialogue.

Description: Released the same year as '10 Things I Hate About You', this teen rom-com similarly features opposites attracting through a scheme (in this case, pretending to date to make exes jealous). Both films explore themes of social status, authenticity, and unexpected romance, with charismatic leads and colorful late-90s aesthetics. The movies share a similar balance of humor and heart, culminating in climactic dance scenes that resolve the central relationships.

Fact: Originally titled 'Next to You'. Melissa Joan Hart cut her signature long hair for the role. The film's soundtrack featured popular late-90s artists like Britney Spears.