This coming-of-age film follows the mayhem of group of rowdy teenagers in Austin, Texas, celebrating the last day of high school in 1976. The graduating class heads for a popular pool hall and joins an impromptu keg party, however star football player Randall "Pink" Floyd (Jason London) has promised to focus on the championship game and abstain from partying. Meanwhile, the incoming freshmen try to avoid being hazed by the seniors, most notably the sadistic bully Fred O'Bannion (Ben Affleck).

Five high school students from different walks of life endure a Saturday detention under a power-hungry principal (Paul Gleason). The disparate group includes rebel John (Judd Nelson), princess Claire (Molly Ringwald), outcast Allison (Ally Sheedy), brainy Brian (Anthony Michael Hall) and Andrew (Emilio Estevez), the jock. Each has a chance to tell his or her story, making the others see them a little differently -- and when the day ends, they question whether school will ever be the same.

Kat Stratford (Julia Stiles) is beautiful, smart and quite abrasive to most of her fellow teens, meaning that she doesn't attract many boys. Unfortunately for her younger sister, Bianca (Larisa Oleynik), house rules say that she can't date until Kat has a boyfriend, so strings are pulled to set the dour damsel up for a romance. Soon Kat crosses paths with handsome new arrival Patrick Verona (Heath Ledger). Will Kat let her guard down enough to fall for the effortlessly charming Patrick?

Shallow, rich and socially successful Cher (Alicia Silverstone) is at the top of her Beverly Hills high school's pecking scale. Seeing herself as a matchmaker, Cher first coaxes two teachers into dating each other. Emboldened by her success, she decides to give hopelessly klutzy new student Tai (Brittany Murphy) a makeover. When Tai becomes more popular than she is, Cher realizes that her disapproving ex-stepbrother (Paul Rudd) was right about how misguided she was -- and falls for him.