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In Harold and Maude, a 20-year-old who stages fake suicides for attention falls for a woman about to turn 80. The 1971 film lost money on release and is now a cult classic taught in film courses. It belongs to a small group of movies that take a pairing most viewers would call impossible and treat it as ordinary. Most were attacked or quietly released, then found later by viewers the studios never expected. These films share little beyond that refusal to flinch, and the best of them are decades old. They endure because of the filmmaking, and the strangeness of each couple is the smallest part of why they last.
Harold and Maude and the Age-Gap Taboo
Harold and Maude pairs a death-obsessed young man with Maude, a 79-year-old who steals cars and models for sculptors. Ruth Gordon played Maude and Bud Cort played Harold, and director Hal Ashby kept the romance mostly off-screen so the friendship could sustain the film. Colin Higgins wrote the screenplay as his graduate thesis, and he later reused its morbid comic tone in his script for the hit Nine to Five. The soundtrack by Cat Stevens became as well known as the movie itself. Critics dismissed it in 1971, and Paramount nearly buried it. It found its audience in repertory houses, where it played for years, and the Library of Congress added it to the National Film Registry in 1997. The age gap is the premise, but the film treats Maude’s appetite for living as its center, and Harold’s change follows from that. The pairing works because the script never asks the viewer to be scandalized by it.
Breakfast at Tiffany’s
Holly Golightly spends Breakfast at Tiffany’s searching for a wealthy older man to marry, while her neighbor Paul is kept by an older woman who pays his bills. Blake Edwards directed the 1961 adaptation of Truman Capote’s novella, with Audrey Hepburn as Holly and George Peppard as Paul. Both leads use their appeal as a source of income. Holly’s pursuit of a sugar daddy drives the plot, even though the film softens Capote’s harder portrait of her. The song “Moon River,” written by Henry Mancini and Johnny Mercer, won the Academy Award for Best Original Song. Capote disliked the result and Hepburn’s casting, since he had pictured a rougher character, and Mickey Rooney’s caricature of a Japanese neighbor remains the film’s most criticized choice. Still, the movie made the pairing glamorous, and it lasted. It is one of the few studio films of its era to build a romance around money and dependency and punish no one for it.
Open Marriage in Bob & Carol & Ted & Alice
The 1969 comedy follows two married couples who decide to drop the rules after one pair returns from a therapy retreat preaching total honesty. Natalie Wood, Robert Culp, Elliott Gould, and Dyan Cannon played the four leads, and Paul Mazursky directed it as a satire of the era’s encounter-group culture and its flirtation with open marriage. The film stops short of the foursome it sets up, and that hesitation became its most discussed feature. It ends with the four in bed together and then choosing not to go further, a finish that withholds the payoff its premise promised. It earned four Academy Award nominations, rare for a studio comedy about swinging, with nods for Gould and Cannon among them. The couples talk about openness far more than they practice it, and the distance between the talk and the act is the joke.
Vicky Cristina Barcelona and the Triangle
Woody Allen’s Vicky Cristina Barcelona, released in 2008, sends two American friends, played by Scarlett Johansson and Rebecca Hall, to Barcelona, where both become involved with the painter Juan Antonio and then with his volatile ex-wife Maria Elena. Javier Bardem and Penelope Cruz played the Spanish couple. The three settle into a household that works until it does not. Cruz won the Academy Award for Best Supporting Actress, and the film took the Golden Globe for Best Motion Picture in the musical or comedy category. The story presents the three-way without the punishment such plots usually impose. Cristina leaves on her own terms, and the film stages no penalty for the months she spent inside it. Allen treats jealousy as the practical problem the trio cannot solve, and he lets the audience sit with that.
Professor Marston and the Wonder Women
This 2017 film dramatizes the real home of William Moulton Marston, the psychologist who created Wonder Woman. Angela Robinson directed it, with Luke Evans as Marston, Rebecca Hall as his wife Elizabeth, and Bella Heathcote as their partner Olive Byrne. Marston helped invent an early lie-detector test and developed the DISC theory of personality, and the three adults lived together for years and raised children. The movie ties his creation of the character to the polyamorous household and its ideas about power and submission. It was one of the few mainstream films to present a three-person relationship as functional. Critics praised Hall’s performance, and the film struggled at the box office despite strong reviews. The family kept the household private during their lives, and the film treats that secrecy as the cost they paid for it.
Secretary and the Power Exchange
Steven Shainberg’s Secretary, released in 2002, follows a young woman who takes a job with a demanding lawyer and finds that a dominant and submissive relationship suits her better than the conventional one she is offered later. Maggie Gyllenhaal and James Spader play the pair in a story adapted from a Mary Gaitskill short story. Spader plays the lawyer as withdrawn and exacting, and the office becomes the one place either of them feels understood. The film was unusual for treating the dynamic as a path to stability. It premiered at Sundance, where it won a Special Jury Prize for originality, and built a following that outlasted its small theatrical release. The relationship is a fit between two specific people, and it has aged better than most films on the subject.
The Long Afterlife of These Films
Harold and Maude lost money in 1971 and is now part of the canon of films studied as classics, which is the pattern across most of this list. Studios rarely greenlight stories like these, and the list reaches back more than 60 years. Unconventional here means a pairing the surrounding culture had no ready script for at the time of release. Each film works by declining to treat its couple as a problem the plot must fix. The discomfort that met these movies on release faded, and the films outlived it by decades.
