What a Way to Go!

What a Way to Go! is a 1964 American black comedy directed by J. Lee Thompson and starring Shirley MacLaine, Paul Newman, Robert Mitchum, Dean Martin, Gene Kelly, Bob Cummings and Dick Van Dyke.

Plot

In a dream-like pre-credit sequence, Louisa May Foster (Shirley MacLaine), dressed as a black-clad widow, descends a pink staircase in a pink mansion. As she reaches the bottom, she is followed by pall-bearers carrying a pink coffin. As they round the bend in the staircase, the pallbearers drop the coffin, which slides down the stairs, leading into the opening titles.

Louisa tries to give away more than $200 million to the U.S. government Internal Revenue Service, which believes it an April Fools' Day joke. Louisa ends up sobbing on the couch of an unstable psychiatrist (Robert Cummings). Louisa tries to explain her motivation for giving away all that money, leading into a series of flashbacks combined with occasional fantasies from Louisa's point of view.

We meet Louisa as a young, idealistic girl. Her mother (Margaret Dumont in her final film role), fixated on money, pushes for Louisa to marry Leonard Crawley (Dean Martin), the richest man in town. Louisa instead chooses Edgar Hopper (Dick Van Dyke), an old school friend who, inspired by Henry David Thoreau, lives a simple life. They marry and are poor but happy, shown through a silent film spoof with the underlying motif, "Love Conquers All." Their life is idyllic until Hopper, hurt and angry by Crawley ridiculing how they live, decides to aim for success. Neglecting Louisa in order to provide a better life for her, he builds his small store into a tremendous empire, running Crawley out of business. But in so doing, Hopper literally works himself to death.