Marilyn Monroe spends most of How to Marry a Millionaire refusing to wear her glasses, on the theory that men do not make passes at women who can see. The joke works because the film knows exactly what its heroines are doing and refuses to punish them for it. Hollywood has been telling that story for 70 years, sometimes with sympathy and sometimes with a moral tacked on at the end.
The films that handle the subject well span 1953 to 2018, and what changed across them is the audience’s tolerance for a heroine who admits the money matters to her.
How to Marry a Millionaire (1953)
Three women pool their money to rent a Manhattan penthouse they cannot afford, on the reasoning that rich men do not visit cheap apartments. Monroe, Lauren Bacall, and Betty Grable play it broad, and Nunnally Johnson’s script gives each of them a different position on what they are willing to accept in a husband.
It was the first film 20th Century Fox shot in CinemaScope, made for $1.9 million and returning $8 million, one of the studio’s biggest hits of the decade. Bacall’s Schatze is the sharpest character, a woman who has done the arithmetic and states her terms without embarrassment, and the film lets her end up somewhere she did not plan without treating that as a lesson.
Breakfast at Tiffany’s (1961)
Audrey Hepburn’s Holly Golightly is the most imitated character on this list and the most misread. Blake Edwards films her as a charming eccentric, while Truman Capote’s novella is clearer about how she pays her rent, and the tension between the two versions is what keeps people arguing about the film 60 years later.
The Mickey Rooney performance as Mr. Yunioshi is indefensible and unavoidable, and any recommendation has to say so. What survives is Hepburn’s reading of a woman who has built an entire personality as a working instrument, and George Peppard’s Paul, who is being kept by an older woman and never quite says the word for it.
The film took five Oscar nominations and won two, both for Henry Mancini, one shared with lyricist Johnny Mercer for Moon River. Hepburn was nominated for Best Actress and lost. The result was correct and still feels wrong.
Pretty Woman (1990)
Garry Marshall’s film grossed $463 million worldwide and rewrote the romantic comedy for a decade. The original script was a bleak drama about class and addiction, and the studio turned it into a fairy tale, which is why the movie feels like two films stitched together and why the seams are the interesting part.
Julia Roberts does something difficult in it. She plays a woman who understands her own position exactly and refuses to be embarrassed about it, and the shopping sequence works because the humiliation comes first and the correction is hers to enjoy. Richard Gere has the harder job and mostly disappears into it, and the film needs him to, since the fantasy collapses the moment the audience starts studying him.
Indecent Proposal (1993)
Adrian Lyne’s film asks one question for two hours. A billionaire offers a married couple $1 million for a night with the wife, and the answer they give matters less than what the offer reveals about the marriage they already had.
It grossed close to $267 million worldwide and was mocked by critics on release, but the mockery aged worse than the film. The Indecent Proposal premise still circulates as a hypothetical in bars and podcasts, which is the sort of afterlife most 1990s dramas never get. Demi Moore and Woody Harrelson are both good, and Robert Redford plays the buyer with a gentleness that makes the whole thing worse.
Titanic (1997)
James Cameron’s film pushed past the $2 billion mark across its releases, and the ship is only half of what people came back for. The other half is a young woman engaged to a wealthy man she does not love, choosing a penniless one, in front of her mother, who has explained precisely what that choice costs the family.
Cameron takes Rose’s dilemma seriously. Billy Zane’s Cal is written as a monster, which is the film’s weakest choice, since a woman weighing a life with a sugar daddy against one with a penniless artist has been a staple of love stories since the silent era, and the choice only holds if both sides of it are real. The story still works because Rose’s options are genuinely narrow.
Frances Fisher’s single scene about what happens to unmarried women without money says more about Rose’s position than any speech Jack gets.
The Great Gatsby (2013)
Baz Luhrmann’s version opened to $51.1 million and finished with $353 million worldwide, and its excess is a defensible reading of the novel. Fitzgerald wrote a book about a man who assembled a fortune as an argument aimed at one person, and Luhrmann films the argument at full volume. Leonardo DiCaprio’s Gatsby is the best performance in any Great Gatsby adaptation, and Carey Mulligan finds the frightened calculation in Daisy that most versions flatten into vanity. The film is loud, and the party scenes go on too long, and both of those things are the point.
Crazy Rich Asians (2018)
Jon M. Chu’s Crazy Rich Asians opened to $35 million across five days and took $238 million worldwide against a $30 million budget and was the first major studio release with a nearly all-Asian cast since The Joy Luck Club in 1993. The love story is conventional and the money drives every turn of it, since the conflict is about a family that regards Rachel as an unserious American who will not sacrifice for the collective.
The mahjong scene is the best-written sequence on this list. Two women play a game while conducting a negotiation neither states aloud, and Michelle Yeoh loses the hand on purpose to make a point about who is actually surrendering. Constance Wu plays it as an economist would, since her character is one.
The Reversal Between 1953 and 2018
Schatze Page announces her terms in the first reel of a 1953 comedy, and nobody in that film shames her for it. Rachel Chu, in 2018, has to demonstrate that she wants nothing at all before the family will have her. Seventy years produced a heroine required to be indifferent to money in a way the 1950s never demanded of anyone.
That comparison is the uncomfortable part of watching these in sequence, and it explains why the older titles still play so well. A 1953 screenwriter could put wealth and marriage in the same sentence and let a character do the arithmetic out loud. The modern version hands the arithmetic to the antagonist and asks the heroine to prove she never did it.