Unemployable due to his inability to do things right, Bob (Tom Green) decides to approach jobs by trying them all in alphabetical order. After flunking every A-letter job, he moves on to the B's and ends up working as a butler to Anne Jamieson (Brooke Shields), an overly tidy woman with two children, Tess (Genevieve Buechner) and Bates (Benjamin Smith). The kids take a liking to Bob, despite the fact that he's not the best butler or baby sitter, while Anne slowly realizes the joys of family.