Published on April 1, 2026
When widow Louisa May Hopper Flint Anderson Benson attempts to donate $211 million to the U.S. Treasury, she is directed to a psychiatrist. Louisa, portrayed , expresses her disdain for money, stating that her ultimate goal is happiness. However, there’s a peculiar pattern: every time she marries, her current husband strikes it rich… and then dies unexpectedly.
Louisa recounts her life in flashbacks, detailing her marriages to a range of characters including a Thoreau-reading store owner (Dick Van Dyke), an avant-garde artist (Paul Newman), a successful businessman (Robert Mitchum), and a corny performer (Gene Kelly).
Released in 1964, *What a Way to Go!* is a whimsical comedy boasting impressive credentials. The script was written and Adolph Green, a duo known for crafting some of the most cherished musicals of the 1950s, including *Singin’ in the Rain*. The film garnered Academy Award nominations for Best Art Direction and for costumes designed and Moss Mabry.
The film’s lavish costumes warrant attention, as Shirley MacLaine dons over a dozen stunning outfits throughout the story. These range from a breathtaking backless swimsuit to an evening gown that dazzles like diamonds and a playful all-pink ensemble complete with a pink wig and gloves. MacLaine herself remarked that *What a Way to Go!* featured “pretty good perks,” including working with Edith Head on a budget of $500,000, along with seventy-two hairstyles to complement the gowns, and a $3.5 million collection of gems from Harry Winston in New York.
Among the film’s four subplots, the segment featuring Gene Kelly as Pinky Benson, a small-town entertainer, stands out. After years of performing the same uninspired musical-comedy routine at a local eatery, Louisa persuades Pinky to embrace his authentic self for his final act. Clad in a suit, he performs a romantic song and skyrockets to fame. However, with success comes a transformation into an egomaniac, culminating in a five-and-a-half-hour film dubbed *Flaming Lips*. When a studio executive proposes he star in a remake of *The Four Horsemen* alongside icons like Frank, Marlon, and Cary, Pinky quips, “Why should I carry those deadweights? I’ll play all four.”
This narrative also features an extravagant musical number with MacLaine and Kelly, who, while not as polished a dancer as Vera-Ellen or Cyd Charisse, partners well with Kelly in a homage to *Follow the Fleet*.
Interestingly, *What a Way to Go!* was initially intended for Marilyn Monroe, but following her untimely death, Shirley MacLaine stepped into the lead role. One can’t help but wonder how Monroe might have approached the character, although it is likely that the screenplay was adjusted to highlight MacLaine’s unique talents.
Frank Sinatra and Gregory Peck were considered to play one of Louisa’s husbands. There were even discussions about including Fred MacMurray as a sixth husband, but this idea was likely abandoned to keep the film’s runtime manageable.
While *What a Way to Go!* may not rank among Shirley MacLaine’s finest films, it delivers a dose of lighthearted entertainment that occasionally sparks genuine laughter.
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