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 (Bob 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.
Now a millionaire, Louisa vows never to marry again. She travels to Paris, where she meets Larry Flint (Paul Newman), an avant-garde artist who is driving a taxi. Louisa falls in love with Flint and they marry, living an idyllic life and bohemian lifestyle, shown through a foreign-film spoof. Flint invents a machine which converts sounds into paint on canvas. One day, Louisa plays classical music and it produces a beautiful painting which Flint sells (his first significant sale). Buoyed by success, he creates more and more paintings, becoming hugely successful. Obsessed now, he builds larger machines to do the painting. Flint relentlessly produces art until, one night, the machines turn on their creator and beat him to death.
Even richer but more depressed, Louisa decides to return to the United States. She misses her flight, but meets Rod Anderson (Robert Mitchum), a well-known business tycoon. He offers her a lift on his jet, Melissa. At first she finds him cold and calculating, but Louisa sees his softer side on the flight. They are married shortly after landing. They live a lush and idyllic life, depicted through a fantasy sequence spoofing the glamorous big-budget films of the '50s. Fearful of losing him like her first two husbands if he threw himself back into his work, Louisa convinces Rod to sell everything and retire to a small farm and to Melissa, his prized cow. Rod mistakenly attempts to milk Melrose, his bull, who kicks him through the wall of the barn, leaving Louisa a widow again.
Now fantastically wealthy, Louisa wanders the United States. In a café in a small town, she meets Pinky Benson (Gene Kelly), a performer who does corny musical numbers in clown makeup and costume. Management loves him because Pinky's act never distracts the customers from eating and drinking. Once again, Louisa falls in love and gets married. They live an idyllic life on Pinky's run-down houseboat, depicted through a film sequence spoofing big Hollywood musicals. On her husband's birthday, Louisa suggests that Pinky perform without make-up, to save time. Never noticed before, Pinky is suddenly noticed by the customers. Virtually overnight, he becomes a Hollywood star. Variety headline (dated Wednesday, August 7, 1963) proclaims, "Benson Boffo Bistro Balladeer". He neglects his wife in his pursuit of fame. Another Variety headline (dated Wednesday, October 2, 1963), "Benson Broadway B.O. Bonanza". Everything in his life is pink. A further Variety headline proclamation (dated Wednesday, January 29, 1964), "Pinky Quick Click in Pix with Slick Flicks". He is such a beloved star, Pinky's adoring public tramples him to death after the premiere of one of his films. (His is the funeral we see in the opening scene.)
After listening to her story, the psychiatrist proposes to Louisa, who turns him down, after which he suffers an accident and is knocked out. In comes the janitor, who Louisa recognizes as Leonard Crawley (Martin), no longer the wealthy man he used to be. Leonard and Louisa marry, living a poor but idyllic life on a farm with their four children. The story ends when Leonard apparently strikes oil with his tractor. Louisa becomes distraught, thinking her curse has struck again, until oil company representatives show up and inform them that Leonard has merely damaged a pipeline. They are still poor but happy.
When the film began production in 1962, the role of Louisa May Foster had been intended for Marilyn Monroe, and the original script had been tailored to fit her talents. The film had been assigned to Monroe as a part of her new contract she had signed with 20th Century-Fox, stating that she would be paid $1 million to star in What a Way to Go! and to complete the troubled Something's Got to Give. After Monroe's death, filming was postponed, until Shirley MacLaine was hired the following year.
Ironically, the swimming pool set in the Pinky Benson sequences is the same set (with some minor redressing) used for Something's Got to Give.
MacLaine was quoted as saying that she was happy to work with "Edith Head with a $500,000 budget, 72 hairstyles to match the gowns, and a $3.5-million gem collection loaned by Harry Winston of New York. Pretty good perks, I'd say."
Robert Mitchum's role was originally meant for Frank Sinatra but Sinatra suddenly wanted several times more money than what the other male leads received. The studio refused Sinatra's demands; Gregory Peck was sought but he was unavailable. Shirley MacLaine recommended Mitchum to director J. Lee Thompson who recommended him to the studio.
What a Way to Go! premiered on May 12, 1964, and grossed $11,180,531 at the US box office, earning $6.1 million in US theatrical rentals. It was the 11th highest grossing film of 1964.
What a Way to Go! was nominated for Academy Awards for Best Art Direction (Jack Martin Smith, Ted Haworth, Walter M. Scott, Stuart A. Reiss) and Best Costumes by Edith Head and Moss Mabry, a BAFTA Best Foreign Actress Award for Shirley MacLaine, a Laurel award for Best Comedy and Best Comedy performer for Paul Newman, and an American Cinema Editors Eddie award for best editor for Marjorie Fowler. It won a Locarno Film Festival award for Best Actor for Gene Kelly.