Corporate drone Peter Gibbons (Ron Livingston) hates his soul-killing job at software company Initech. While undergoing hypnotherapy, Peter is left in a blissful state when his therapist dies in the middle of their session. He refuses to work overtime, plays games at his desk and unintentionally charms two consultants into putting him on the management fast-track. When Peter's friends learn they're about to be downsized, they hatch a revenge plot against the company inspired by "Superman III."

In Seattle during the era of grunge music, the lives and relationships of a group of young people, all living in the same apartment building, go through a period of flux. Among them are waitress and aspiring architect Janet (Bridget Fonda), who finds herself obsessed with bad boy musician Cliff (Matt Dillon) ; Linda (Kyra Sedgwick), an emotionally fragile environmentalist on the look-out for love; and Steve (Campbell Scott), a quintessential nice guy who studies traffic patterns.

Ted's (Ben Stiller) dream prom date with Mary (Cameron Diaz) never happens due to an embarrassing injury at her home. Years later, Ted hires Pat Healy (Matt Dillon) to track down Mary so he can reconnect with her. Pat lies to Ted about Mary and he finds out everything he can about her to trick her into dating him. Ted travels to meet Mary and has to weave through the web of lies that Pat and Mary's friend Tucker (Lee Evans) have woven to try and win her over.