Rob Gordon (Cusack) is the owner of a record store in Chicago, where he sells music the old-fashioned way -- on vinyl. He's a self-professed music junkie who spends his days at ''Championship Vinyl'' with his two employees, Dick (Louiso) and Barry (Black). When his long-time girlfriend, Laura (Hjejle), walks out on him, he examines his failed attempts at romance and happiness, and finds himself being dragged, kicking and screaming, into adulthood.