Best Old-School Teen Films from the 90s to Early 2000s

Description: Although slightly before the 90s, this film is a cornerstone of teen cinema, where five high school students from different social groups spend a Saturday in detention together, learning about each other's lives.

Fact: The film was shot in sequence over 28 days, and the actors were encouraged to improvise, leading to many spontaneous moments.

Description: Although from the 80s, this film's influence on teen culture extends into the 90s. Ferris, a high school student, fakes illness to enjoy a day off with his friends, teaching life lessons along the way.

Fact: The film was shot in Chicago, and the parade scene was a real event, with the actors inserted into the footage.

Description: Set on the last day of school in 1976, this film follows various groups of teenagers as they party, cruise, and contemplate their future, encapsulating the laid-back vibe of the era.

Fact: Many of the actors, including Matthew McConaughey, were discovered through open casting calls.

Description: A modern adaptation of Jane Austen's "Emma," this film follows Cher, a rich and popular high school student, as she navigates the complexities of love and friendship. Its witty dialogue and fashion have made it a timeless classic for teens.

Fact: The film popularized the term "as if" and its fashion, particularly plaid skirts and knee-high socks, became iconic.

Description: Set at a high school graduation party, this film intertwines multiple stories of love, revenge, and self-discovery among the attendees, capturing the essence of the end of high school.

Fact: The film features an ensemble cast with many actors who would later become stars, and it was one of the first films to use the internet for promotion.

Description: This film delves into the pressures of high school football in a small Texas town, focusing on the team's star quarterback and his teammates as they face personal and athletic challenges.

Fact: The film was inspired by real-life stories of high school football culture in Texas, and it features a now-iconic scene with whipped cream.

Description: A modern take on Shakespeare's "The Taming of the Shrew," this movie features a plot where a new student pays a bad boy to date the sister of his crush. It's filled with humor, romance, and memorable performances.

Fact: Heath Ledger's performance of "Can't Take My Eyes Off You" was improvised, and the poem read by Kat at the end was written by Julia Stiles.

Description: A popular jock makes a bet that he can turn an unpopular girl into the prom queen, leading to unexpected romance and self-discovery. This film captures the essence of high school popularity contests and personal transformation.

Fact: The movie was inspired by "Pygmalion" and "My Fair Lady," and it features one of the earliest performances by Anna Paquin.

Description: A group of high school friends make a pact to lose their virginity by prom night, leading to a series of comedic and heartfelt moments. It's a raunchy yet endearing look at teenage sexuality and friendship.

Fact: The film was initially rated NC-17 but was edited down to an R rating. It spawned several sequels and a spin-off series.

Description: A new student navigates the treacherous waters of high school popularity, dealing with "The Plastics," a group of mean girls. It's a sharp, funny, and insightful look at high school social dynamics.

Fact: The screenplay was written by Tina Fey, and the film includes many now-iconic lines and scenes.