Hard-as-nails Lily Dillon (Anjelica Huston) works as a swindler for dangerous bookie Bobo (Pat Hingle), probably the only man she fears. Arriving in Los Angeles on “business,” Lily looks up her son, Roy (John Cusack), a small-time con artist content with paltry sleight-of-hand cheats. Roy’s girlfriend, Myra (Annette Bening), looks like an All-American type but is a grifter looking to pull off another big-time con. The convergence of the three hustlers inevitably means trouble for all of them.
After learning that a stranger has been accidentally killed near their rural homes, four Oregon boys decide to go see the body. On the way, Gordie Lachance (Wil Wheaton), Vern Tessio (Jerry O’Connell), Chris Chambers (River Phoenix) and Teddy Duchamp (Corey Feldman) encounter a mean junk man and a marsh full of leeches, as they also learn more about one another and their very different home lives. Just a lark at first, the boys’ adventure evolves into a defining event in their lives.
Gib (John Cusack), a college freshman, keeps striking out with women. When he learns that a beautiful Californian (Nicollette Sheridan) wants to have a tryst with him, he decides to carpool all the way to the West Coast to meet her. Unfortunately, one of the other passengers on the trip is Alison (Daphne Zuniga), an attractive but domineering girl who has rejected Gib once before. The journey is a nightmare until a funny thing happens – Gib and Alison start to fall in love.
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.”
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).
With the occasion all but overshadowed by her sister’s upcoming wedding, angst-ridden Samantha (Molly Ringwald) faces her 16th birthday with typical adolescent dread. Samantha pines for studly older boy Jake (Michael Schoeffling), but worries that her chastity will be a turnoff for the popular senior. Meanwhile, Samantha must constantly rebuff the affections of nerdy Ted (Anthony Michael Hall), the only boy in the school, unfortunately, who seems to take an interest in her.
Lane Meyer (John Cusack) is a teen with a peculiar family and a bizarre fixation with his girlfriend, Beth (Amanda Wyss). When Beth dumps Lane, he decides to kill himself, making bumbling attempts at suicide. Outside of his morbid endeavors, Lane spends time with his oddball buddy, Charles (Curtis Armstrong), and befriends Monique (Diane Franklin), a visiting French student. Eventually, Lane resolves to race Beth’s obnoxious new beau on the ski slopes, with unexpected results.