Newly deceased playboy Henry Van Cleve arrives at the outer offices of Hades where he asks a bemused Satan for permission to enter the gates of Hell. Though the Devil doubts he will qualify, Henry proceeds to recount a lifetime wooing and pursuing women.

Eddie is an eighty-three-year-old war veteran. He spends his days maintaining the rides at Ruby Pier, a seaside amusement park. Now Eddie's own life is about to come to an end. One morning, an accident occurs on one of the rides. In front of a horrified crowd, Eddie attempts to save the five-year-old's life. The last thing he sees is the little girl's frightened face, the last thing he feels is the child's hands in his. Then, a blinding flash of light...

Deceased drifter Mike arrives in Heaven and quickly falls for newborn soul Annie, soon to start her assignment on Earth. When Annie leaves, Mike follows, risking all to find her with no memories of their previous existence.