Rob Gordon (John Cusack) is the owner of a semi-failing record store located on one of the back streets of Chicago. He sells music the old-fashioned way - on vinyl, with two wacky clerks: rock snob Barry (Jack Black) and quietly opinionated Dick (Todd Luiso). But Rob's business isn't the only thing in his life that's floundering - Rob's needle skips the love groove when his longtime girlfriend Laura (Iben Hjejle) walks out on him, forcing him to examine his past failed attempts at romance the only way he knows how.