Wealthy New York City playboy Arthur Bach (Dudley Moore) is perpetually drunk and completely rudderless. Dutifully supported by his sharp-tongued and quick-witted butler, Hobson (John Gielgud), Arthur reluctantly prepares to enter into an arranged marriage with heiress Susan Johnson (Jill Eikenberry). When he meets Linda Marolla (Liza Minnelli), a waitress from Queens, he falls head over heels in love, but if he backs out of his engagement with Susan, he may lose his fortune.
Sam (Sam Rockwell) and Eddie (Steve Zahn) are just a couple of clueless, untalented singers. But, when they are mistaken for a pair of safecracking geniuses by a mobster named Veal Chop (Paul Giamatti), they are unwittingly sucked into a life of crime. Though they have no idea what they are doing, Sam and Eddie have no choice but to go along with the Mafia’s orders and break into three safes. Things get even more complicated when Sam falls for the daughter of one of their robbery victims.