Not a great deal has been divulged about Woody Allen’s new movie, Whatever Works—which premieres at the Tribeca Film Festival on April 22, 2009 (the movie opens in wide release June 19). We do know, however, that the movie centers on a May-December romance between a veteran misanthrope (Larry David, 61) and a free-spirited young woman (Evan Rachel Wood, 21).

This should be perfect fodder for Allen, who has visited the May-December theme several times in the course of his long directing career–most notably and successfully in Manhattan (1979), his valentine to his favorite city and a then 17-year-old Mariel Hemingway. In a classic case of life imitating art, several years after Manhattan, the tawdry break-up of Allen’s relationship with Mia Farrow was precipitated when she found compromising photos Allen had taken of Farrow’s adopted daughter—and Allen’s now-wife—Soon-Yi Previn, who is 35 years Allen’s junior.

Given the prospect of watching David woo a woman 40 years younger than him in Whatever Works, MM thought it an opportune time to select six of cinema’s most memorable May-December couples (and not necessarily in a good way).

May-December romances do not, of course, automatically have to be creepy: Summer of ’42 (1971) about a young man having an affair with a somewhat older woman managed to be tender and touching. Bill Murray and Scarlett Johansson’s relationship in Sofia Coppola’s Lost in Translation (2003), while fleeting, nonetheless had the deep emotional resonance of a romance between equals. In The Reader (2008), the affair between a 36-year-old former concentration camp guard (Kate Winslet in an Oscar-winning performance) and a 15-year-old boy surprisingly manages to avoid the serious ick factor of some of our list-makers.

Lolita (1962)
directed by Stanley Kubrick
The studio fudged a bit by having the “nymphet” in Nabokov’s novel—who was supposed to be around 12—played by 16-year-old Sue Lyon. But even so, this portrait of obsession (as embodied by the iconic Humbert Humbert, played by James Mason) and pedophilia was a daring project for moviemaking legend Kubrick to undertake. Although Kubrick doesn’t entirely capture the wonderfully complicated tone and attitude of the novel, the superb movie nonetheless manages to be darkly comic with a tinge of tragedy. (Whereas Adrian Lyne’s 1997 remake had none of the humor but all of the unsettledness.)

Harold and Maude (1971)
directed by Hal Ashby
This cult classic has developed a hard-core fan base over the years. While the movie is not without its trippy/retro charm, the central romance between death-obsessed Harold (Bud Cort) and sprightly octogenarian Maude (Ruth Gordon) is still creepy beyond words. Thankfully director Ashby (Being There, The Last Detail) spares us any graphic love scenes, but just the thought of these two actually, you know, doing it… yuck.

Manhattan (1979)
directed by Woody Allen
At the time of its release, Manhattan was hailed as one of Allen’s finest and drew high praise from critics such as Vincent Canby of The New York Times. Interestingly, Canby—and others—made only passing mention of the disturbing relationship at the movie’s core. As the years have passed and childhood sexual abuse has become more of a societal concern, the central romance between 42-year-old Isaac (Allen) and 17-year-old Tracy (Hemingway) has begun to seem more and more icky. Watching the film today one keeps asking: Doesn’t anyone care that what these two are doing is illegal? Immoral? And where the heck are the young girl’s parents? (The screenplay conveniently ignores them—Isaac and Tracy appear to exist in some alternate universe where a 42-year-old, self-absorbed neurotic and a precocious high school girl can carry on a sexual affair with absolutely no one noticing or caring. Tracy’s parents get only one passing mention in the entire movie.)

Ghost World (2001)
directed by Terry Zwigoff
Based upon Daniel Clowes’ acclaimed graphic novel, Ghost World revolves around the relationship between Enid (Thora Birch), an idiosyncratic 18-year-old trying to find her place in the world after graduating high school, and Seymour (Steve Buscemi), a lonely, middle-aged nerd obsessed with collecting old blues records. In a twist on the usual older man as predator scenario, the affair is initiated by the young girl, who begins their relationship as a sort of cruel prank. While their affair has its sweet side, the two lovers are simply too mismatched and end up pulling away from each other. The movie ends with Enid alone on a bus and Seymour in therapy.

Shopgirl (2005)
directed by Anand Tucker
While not as disturbing as some of the other movies on our list, there is still something unsettling about the relationship between Ray (played by Steve Martin, who adapted the screenplay from his own novel) and Mirabelle (Claire Danes). Ray is a smooth, well-heeled entrepreneur pushing 60; Mirabelle is a bored young woman in her early 20s who aspires to be an artist, and in the meantime sells gloves at a high-end department store. While Ray is in the relationship strictly for sex, Mirabelle understandably wants something more, which is where the tension in the relationship arises. While Ray claims to have Mirabelle’s best interests at heart, there is something vaguely insincere and smarmy in the older man’s attitude toward the young woman.

Venus (2006)
directed by Roger Michell
Peter O’Toole stars as Maurice, a veteran actor who forms a romantic interest in Jessie (Jodie Whittaker), a brash twentysomething girl who is visiting his best friend. It isn’t long before Maurice begins making romantic overtures to Jessie. Watching the skeletal O’Toole flirt with a girl at least 50 years his junior makes for an undeniably creepy experience, especially when Jessie starts setting guidelines for Maurice to touch her (“You can kiss my shoulders… but only three times.”). It’s like watching the Crypt Keeper putting the moves on a young nubile.

Which May-December movie romances is your most memorable? Let us know in the comments section below.