In this study of Generation X manners, Lelaina Pierce (Winona Ryder), the valedictorian of her college class, camcords her friends in a mock documentary of posteducation life. Troy Dyer (Ethan Hawke) is her best friend, a perpetually unemployed musical slacker. Vickie Miner (Janeane Garofalo) is a manager at the Gap who worries about the results of an A.I.D.S. test, while Sammy Gray (Steve Zahn) has problems grappling with his sexuality. When Lelaina meets Michael Grates (Ben Stiller), an earnest video executive who takes her homemade video to his MTV-like station, she must decide what she values - the materialism of yuppie Michael or the philosophical musings of Troy.