Ecstatic when his parents leave on vacation for a few days, high school senior Joel Goodsen (Tom Cruise) cuts loose with his best friend Miles. After an attempt at securing the services of a prostitute goes slightly awry, Joel hires gorgeous Lana (Rebecca De Mornay) for a night of delight. Stunned by the amount of Lana’s “bill” the next morning, Joel grows frantic after he crashes his father’s Porsche. In an effort to raise lots of money fast, a desperate Joel turns the house into a brothel.
After graduating from high school, art school hopeful Hoops McCann (John Cusack) struggles to complete his application to the Rhode Island School of Design. Resigning himself to a summer of boredom, McCann agrees to go along with his best friend, George Calamari (Joel Murray), on a family trip to Nantucket, Mass. But, after McCann and Calamari meet rocker-in-distress Cassandra (Demi Moore), it suddenly looks like it’s going to be “one crazy summer.”
A victim of his own anger, the Kid (Prince) is a Minneapolis musician on the rise with his band, the Revolution, escaping a tumultuous home life through music. While trying to avoid making the same mistakes as his truculent father (Clarence Williams III), the Kid navigates the club scene and a rocky relationship with a captivating singer, Apollonia (Apollonia Kotero). But another musician, Morris (Morris Day), looks to steal the Kid’s spotlight — and his girl.
In a seaside California town, best friends Mac (Mel Gibson) and Nick (Kurt Russell) are on opposite sides of the law. Mac is a former drug dealer trying to clean up his act, while Nick is a high-profile detective trying to take down a Mexican drug lord named Carlos (Raul Julia). Soon Nick’s loyalties are put to the test when he begins an affair with restaurateur Jo Ann (Michelle Pfeiffer) — a love interest of Mac’s — unwittingly leading his friend into a police-orchestrated trap.
Lovely teen Julie Richman (Deborah Foreman) is steeped in the excessive, pink-clad culture of the San Fernando Valley, complete with her narcissistic boyfriend, Tommy (Michael Bowen). At a party, however, Julie falls for an edgy Hollywood punk named Randy (Nicolas Cage), and the two begin an unlikely romance. Torn between fitting in with her superficial friends and embracing a more non-conformist lifestyle, Julie ultimately has to decide to stay with Tommy or take a risk with Randy.
After assassin Martin Blank (John Cusack) has trouble focusing on his work, resulting in a failed assignment, he returns to his hometown, Grosse Point, Mich., for his 10-year high school reunion. There he meets Debi Newberry (Minnie Driver), an old girlfriend that he stood up for the prom. Martin’s secretary (Joan Cusack) sets up a hit for him while he is in town, but Martin starts to reconsider his life. Meanwhile, he is hounded by an unstable rival hit man, Grocer (Dan Aykroyd).