What a Way to Go! (1964, J. Lee Thompson)

One of the greatest forgotten comedies with the best casts ever. Shirley Maclaine is super as a long-suffering woman who wanted a simple life with true love, but all the men she married came into money and became obsessed with success, driving them to their deaths and leaving her with increasingly massive inheritance. My favorite, self-referential part: in telling her story, Maclaine imagines each of her marriages as a different style of movie.

Undercranked silent with Van Dyke:

Maclaine (just after her oscar nomination for Irma la Douce) spurns self-important department store heir Dean Martin in her hometown, instead marrying Dick Van Dyke (of Bye Bye Birdie). After some idyllic months in their crumbling shack, he finds he has a knack for salesmanship and devotes the rest of his short life to business.

Arty Foreign Film with Newman:

Next comes bohemian painter Paul Newman (character name: Larry Flint) who makes a fortune selling artworks painted by machines (and by a monkey). Then to switch things up, Robert Mitchum, who’s fabulously wealthy when he meets her and dies as soon as he attempts to retire to a simpler existence. Finally Gene Kelly, a hack café comic who becomes a star the first time she convinces him to perform without his costume and makeup.

Spendy Hollywood production with Mitchum:

All this is being told to psychiatrist Robert Cummings (Jean Arthur’s love interest in The Devil and Miss Jones) in framing story after she’s caught trying to give away her fortune to the IRS. Maclaine then finds a financially ruined Dean Martin, working as a janitor in the building, who has come to appreciate the simple life after being driven out of business by Dick Van Dyke, and it’s true love.

Musical, of course, with Kelly:

Won a well-deserved oscar for costumes (although it kinda cheated with the parade of self-consciously glamorous dresses in the Hollywood meta-film), and another for art direction, presumably for the house that Gene “Pinky” Kelly has painted entirely pink. Writers Betty Comden and Adolph Green did The Band Wagon, Singin’ in the Rain and On The Town, and Thompson had just made The Guns of Navarone and Cape Fear. Thanks to Joanna for the recommendation.