Billy Bigelow has been dead for 15 years. Now outside the pearly gates, he long ago waived his right to go back to Earth for a day. He has heard that there is a problem with his family: namely with his wife Julie Bigelow, née Jordan, and his child he hasn't met. He would now like to head back to Earth to assist in rectifying the problem; but before he may go, he has to get permission from the gatekeeper by telling him his story. Adapted from the Rodgers and Hammerstein hit Broadway musical.

A young poet named Hoffman broods over his failed romances. First, his affair with the beautiful Olympia is shattered when he realizes that she is really a mechanical woman designed by a scientist. Next, he believes that a striking prostitute loves him, only to find out she was hired to fake her affections by the dastardly Dapertutto. Lastly, a magic spell claims the life of his final lover.