Lelaina (Winona Ryder), freshly graduated from college, decides to make a movie about the lives of her Twentysomething friends: slacker musician Troy (Ethan Hawke), Gap shop manager Vickie, and Vickie’s best friend Sammy (Steve Zahn).
When a smooth music video station executive (Ben Stiller) takes an interest in her, professionally and personally, Lelaina is forced to decide exactly what she wants from life.