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

In the film, a wealthy widow wants to donate most of her fortune to the Internal Revenue Service. She narrates her life story to her psychiatrist. Each of her past husbands found wealth and success, but met with tragic deaths. She thinks she is cursed, and she would instead prefer a "simple life" inspired by the writings of Henry David Thoreau.

In a dream-like pre-credit sequence, Louisa, a black-clad widow, descends a pink staircase inside a pink mansion. She is followed by pallbearers carrying a pink coffin. The pallbearers slip and drop the coffin, which slides down the stairs.

Louisa wants to give her $211 million to the U.S. government Internal Revenue Service, who believes it is an April Fools' Day joke. Sobbing to her unstable psychiatrist, Dr. Stephanson, Louisa tries to explain why she wants to give away her money, leading to a series of flashbacks, interspersed with fantasy sequences.

Louisa describes her childhood as a young, idealistic girl in a small town in Ohio. Her money-grubbing mother pushed Louisa to marry rich local business owner Leonard Crawley. Louisa instead marries Edgar Hopper, a poor shop owner who, inspired by Henry David Thoreau, prefers a simple life. They are happily poor until the jilted Leonard arrives and ridicules their rustic lifestyle, humiliating Edgar and motivating him to achieve success. Edgar transforms his small store into a tremendous empire, neglecting Louisa, ruining Crawley, and eventually overworking himself to an early death.

A grieving Louisa travels to Paris where she meets Larry Flint, an impoverished avant-garde artist. They fall in love, marry, and live a picturesque bohemian lifestyle. Larry invents a crane-like machine that converts eclectic sounds into paint strokes on canvas. One day, Louisa plays classical music that produces a beautiful painting, resulting in Larry's first major art sale. Larry builds larger cranes and sells many more paintings, making him a successful artist. One night, two petulant cranes turn on their creator and beat him to death.

Louisa, richer and more depressed, prepares to return to the United States. When she misses her flight, famed business tycoon Rod Anderson Jr. offers her a lift on his private jet. She initially finds him cold and calculating, but sees his softer side during the flight. They marry shortly afterward and live luxuriously in his Manhattan penthouse. Fearful of losing him like her first two husbands, Louisa convinces Rod to retire to a small farm similar to his childhood home. After sharing a jug with a few locals, an inebriated Rod mistakenly attempts to milk a bull, which kicks him through the barn wall, leaving Louisa widowed once again.

Now fantastically wealthy, Louisa wanders the country. In a small-town café, she meets Pinky Benson who, for over a decade, has performed nightly dressed as a clown. Management loves Pinky's corny musical act because it never distracts the customers from eating and drinking. The two fall in love and idyllically live aboard Pinky's run-down houseboat on the Hudson River. On Pinky's birthday, Louisa suggests he perform without his usual time-consuming clown make-up and costume so they will not be late for his party after the show.