Hollywood loves a good romance, but some on-screen pairings raise eyebrows more than others. May-December romances, where a significant age gap exists between partners, can be fascinating, awkward, or just plain bizarre. Here are 10 of the weirdest May-December movie romances that have graced the silver screen.
Cactus Flower (1969)
Cactus Flower features Walter Matthau as Dr. Julian Winston, a dentist feigning marriage to avoid commitment. His young girlfriend, Toni (Goldie Hawn), attempts suicide, leading to more lies and a request for his nurse, Stephanie (Ingrid Bergman), to pose as his wife. The twist? Stephanie loves him! This kooky comedy explores mature love versus youthful infatuation with plenty of laughs along the way.
As Good as It Gets (1997)
Jack Nicholson plays Melvin Udall, a misanthropic novelist, who finds a strange connection with Carol Connelly (Helen Hunt), a waitress and single mother. Melvin’s journey from a rude bigot to someone capable of kindness is sparked by his interactions with Carol and her son. Their unconventional May-December romance blossoms amidst an unusual road trip and personal growth.
Sunset Boulevard (1950)
In Billy Wilder’s dark classic, William Holden is Joe Gillis, a screenwriter who becomes entangled with Norma Desmond (Gloria Swanson), a faded silent film star. The age gap isn’t the strangest part; Norma’s grip on reality is. Joe becomes her gigolo, but his attempts to leave her delusional world lead to a tragic end.
Breezy (1973)
Directed by Clint Eastwood, Breezy tells the story of Frank Harmon (William Holden), a cynical businessman, and Breezy (Kay Lenz), a free-spirited young woman. Their stark differences—generational and lifestyle—make their romance an unlikely match. They decide to enjoy their time together, knowing it might not last, highlighting the contrasts between WWII values and the hippie era.
Alex & the Gypsy (1976)
Jack Lemmon stars as Alex, a bail bondsman, in this quirky romantic comedy. He reconnects with his former mistress, Maritza (Geneviève Bujold), a gypsy woman needing his help. Their 17-year age difference underscores their incompatibility, rooted in cultural contrasts. Alex’s traditional lifestyle clashes with Maritza’s craving for freedom and a nomadic existence.
Blame It on Rio (1984)
Matthew Hollis (Michael Caine) finds himself in a compromising situation in Blame It on Rio when he has a fling with his friend’s daughter, Jennifer, during a vacation. The comedy escalates as Matthew deals with guilt, resists Jennifer’s advances, and tries to keep the affair secret, all while his own marriage crumbles and his friend is also involved in an extramarital affair. The fact that he knew her since she was a baby makes the concept even more uncomfortable.
Obsession (Circle of Two) (1981)
Obsession (originally titled Circle of Two) explores the intense, albeit unphysical, relationship between 60-year-old artist Ashley St. Clair (Richard Burton) and 16-year-old Sarah Norton (Tatum O’Neal). Despite Sarah’s passionate pursuit, Ashley refuses to cross the line. The film delves into themes of unrequited love and the complexities of age and desire. It’s widely considered creepy due to the extreme character portrayals within their age groups.
The Graduate (1967)
Dustin Hoffman is Ben Braddock, a recent college graduate seduced by Mrs. Robinson (Anne Bancroft), his father’s business partner’s wife. The Graduate evolves into a story about hypocrisy, loss of innocence, and breaking societal norms as Ben falls for Mrs. Robinson’s daughter, Elaine (Katharine Ross), leading to a rebellious act at Elaine’s wedding.
The Humbling (2014)
Al Pacino plays Simon, an aging actor involved with Pegeen (Greta Gerwig), a much younger woman in The Humbling. Pegeen’s longtime crush on Simon complicates matters, overshadowing the May-December dynamic with other issues. Themes of mental health, sexual identity, and career struggles interweave in this dramedy.
Harold and Maude (1971)
Harold and Maude is a cult classic about the unlikely friendship and romance between 20-year-old Harold (Bud Cort) and 79-year-old Maude (Ruth Gordon). Harold, obsessed with death, finds life lessons from the spirited Maude. Their unconventional relationship challenges societal norms and celebrates living life to the fullest, no matter your age.
These May-December romances offer a glimpse into the complexities of relationships that defy societal norms. Whether they’re funny, tragic, or downright strange, they certainly leave a lasting impression.
What do you think about these unconventional pairings? Leave your comment below!
