Rob Gordon (John Cusack) is the owner of a semi-failing record store in Chicago where he sells music the old fashioned way - on vinyl. He's a music junkie who spends his days at his store, Championship Vinyl, with his two employees Dick (Todd Louiso) and Barry (Jack Black) creating their all-time favorite top-five lists of songs. Although they have an encyclopedic knowledge of pop music and are consumed with the music scene, it's of no help to Rob when his long-time girlfriend Laura (Iben Hjejle) walks out on him. This hilariously funny comedy examines Rob's failed attempts at romance and happiness, as he is dragged kicking and screaming into adulthood.