There’s nothing quite like the May-December romance in which one partner is significantly older than the other. Mainstream movies frequently depict an aging leading man with a much-younger rising starlet – just think of any movie in the James Bond franchise. So the less frequent situation – at least by Hollywood standards – when an older leading lady hooks up with a much-younger rising star understandably draws more attention.

Older Women in May-December Romances

In the reversed situation (older man with much-younger woman), the female partner generally looks for a father figure, as in the case of Charade where Audrey Hepburn’s character seeks the comfort and wisdom of an older man (Cary Grant) during a time of crisis. Likewise, younger men attracted to older women (cougars) usually seek the maternal love they didn’t get as children and still crave as adults. Naturally, the objects of their desire aren’t stodgy little old ladies in tennis shoes, but women who exude a powerful mixture of physical attractiveness and personal confidence.

The Strange Case of Harold and Maude

Highly uncommon films, such as the defiant 1971 cult classic Harold and Maude, represent exceptions to this rule. In this movie, Harold (Bud Cort) and Maude (Ruth Gordon) lack the idealized physical traits associated with romantic comedy leads, she is 60 years his senior, and their “meet cute” scene takes place at a funeral. Even so, this dark romantic comedy fits into the May-December tradition of a sexually charged version of his mother (or perhaps his grandmother) teaching the much younger man the ways of the world, and providing the love he never received in his childhood.

Can May-December Romances Last?

Because these pairings begin with built-in problems – such as generational differences in attitudes, family and friend disapproval, varied stages in the life cycle – any additional challenges can overwhelm the couple. Therefore, like in traditional off-screen love relationships, in about half the cases these romances end with a traumatic breakup. So be warned, in the following list of best May-December romance movies, the ending isn’t always happy.

Romantic Leading Ladies: Michelle Pfeiffer, Sandra Bullock, Helen Mirren, Cher, Anne Bancroft