10 Weirdest May-December Movie Romances

by World's Top Insider Team
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The May-December movie romances mark the romantic tales or movies where one of the partners is significantly older than the other. This fascinating age gap and differences between the couple have fascinated the filmmakers and audiences. These on-screen couples can be very complex and intriguing which makes us wonder how the filmmaker dared to cast the characters in this way.

Let’s delve into ten of the most intriguing and weird May-December movie romances: 

 

10) Cactus Flower (1969)

Source: Wikipedia

It is a 1969 film directed by Gene Saks, a romantic comedy that explores the complexities of relationships and identity. The movie starring Ingrid Bergman, Walter Matthau and Goldie Hawn intrigued the audiences with its vivid themes. It revolves around the dentist Dr. Julian Winston who likes freedom so much that he often makes reasons or pretends to be married so no one could expect a commitment from his side. However, when he meets a 21-year-old record store clerk Toni she attempts suicide because Dr.Julian is unable to commit it. This in return leaves Dr.Julian with no choice but to marry her, by telling her that he and his wife are divorcing. 

Toni marries him but is curious to know about his wife, who didn’t exist. The movie further unfolds complex relationships and identity crises after being stuck in a love triangle. 

 

9) As Good As It Gets (1997)

Source: Wikipedia

The 1997 romantic film explores heartwarming and witty themes of romantic comedy. It is directed by James L. Brooks. The movie featured the main role of Jack Nicholson as Melvin Udall who is a bigoted and misanthropic romance novelist. His personality makes it very challenging to interact with an individual. However, beneath this appearance, there is a deep vulnerable character hidden. Helen Hunt played by Carol Connelly, is a love interest of Melvin who is a single mother and diner waitress. Her remarkable soft personality made Melvin attracted to her. The story then unfolds the intriguing transformation of Melvin. 

Despite the age difference between Melvin and Carol their romance blossoms evolving into mutual understanding and love.

 

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8) Sunset Boulevard (1950)

Source: Wikipedia

This 1950 classic noir movie presents a unique and intriguing May-December romance. It portrays the love interest or romance between William Holden playing the lead role of Joe Gillis and his beau, Gloria Swanson as Norma Desmond. The age difference between the couple is almost twenty years between a thirty-year-old amateur screenwriter and a fifty-year-old faded silent film legend. 

 

7) Breezy (1973) 

Source: Wikipedia

The Breezy is said to be the directorial debut of Clint Eastwood. It revolves around the romantic relationship between a free-spirited young woman and a cynical and feeble middle-aged man. The main lead of the movie is William Holden opposite Kay Lenz, who navigates the complexities of a May-December romance which is set in the 1970s movement. 

The themes of the movie are set to revolve around inter-generational relationships and the traditions that are driven by the power of love. 

 

6) Alex & The Gypsy (1976)

Source: Wikipedia

This 1976 romantic & comedy classic movie is directed by John Korty. It is based on a classic novel by Stanley Elkin, The Bailbondsman. The movie revolves around the re-union of a bail bondsman and his young virgin mistress. Their age difference is very significant and gives proof of their incompatibility. The role is played by Jack Lemmon as Alex, a confused handsome man opposite Genevieve Bujold as Maritza, a beautiful young lady who is 17 years younger than him. There are many indifferences between the couple but despite all that, they are re-united by their fate. 

 

5) Blame It On Rio (1984)

Source: Wikipedia

This 1984 film directed by Stanley Donen spirals around the deep themes of taboo and complex relationships. However, the movie is a romantic comedy but these themes add thrill for the audiences. The characters in the movie are Michael Caine, Michelle Johnson and Valerie Harper who are bonded by the challenges of life like marriage and love. It is a very thought-provoking movie with hints of comedy and laughter. Some scenes might be uncomfortable to watch but their themes are very fascinating. 

 

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4) Obsession: The Circle Of Two (1981)

Source: Wikipedia

The Obsession: The Circle Of Two is an iconic Canadian movie which is directed by Jules Dassin. It explores sensitive and complex themes of unrequited love and romance between a sixty-year-old feeble artist and a sixteen-year-old school girl. The age difference between the couple had sparked much outrage and backlash. Although the themes of the movie don’t promote physical relationships, audiences don’t like the idea of romanticizing an inappropriate relationship. It revolves around the challenges that come with age differences and traditional notions of love. 

 

3) The Graduate (1967)

The 1967’s iconic film is directed by Mike Nichols. It is adapted from or based on Charles Webb’s novel with intriguing themes of satire, comedy and complexities of May-December romances. The movie revolves around Ben Braddock played by Dustin Hoffman who finds himself between two women. The film also features and revolves around the themes of lust and love. These themes are portrayed by the Ben’s affair with Mrs.Robinson, which has a romantic connection with lust. Meanwhile, Ben’s relationship and romantic connection with Elaine symbolises the genuine love and emotional bond. This movie remains acclaimed due to the intriguing messages and themes of love, self-discovery and breaking stereotypes of societal norms, which is evident from disruption of Elaine’s arranged marriage.

 

2) The Humbling (2014) 

Source: Wikipedia

The Humbling is a 2014 movie based on the novel of Philip Roth. It is a very thought-provoking romantic comedy movie that revolves around the life of a lead protagonist Simon played by the legendary Al Pacino. The movie is directed by Barry Levinson that navigates the turbulent life of Simon and the complexities of love. The movie also revolves around the fragility of human mental health and the complexities that come with love and compassion. 

 

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1) Harold and Maude (1971)

The Harold and Maude is a 1971 classic movie directed by Hal Ashby. It defies the stereotypes of romantic love by portraying the friendship turned into a love story. The movie revolves around a young man and a feeble woman. The theme of the movie is quite disturbing, as it intricately reveals the fascination with the death of the lead actor Harold played by Bud Cort. Harold’s character reveals a dark side of faking death and attending funerals for entertainment. The story begins when the main lead actress,

Maude played by Ruth Gordon a 79-year-old woman who is full of life meets Harold at the funeral. The opposite side of nature between Harold and Maude attracts tension in the audience. The film portrays a romantic deep connection and conversations about life and death. Moreover, the intricate details of emotional intimacy transcending the age differences reveal the purity of love and affection. 

Initially, when the movie was released it was met with backlash. It was misunderstood by masses of people until they started watching the movie. The movie gained a cult following as its message inspired the masses. Moreover, the audiences were moved by the charm and delicate depth of the movie making Harold and Maude a timeless dark romantic comedy movie of all time.

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