Harold and Maude
There is no lovelier May-December romance than that of Harold and Maude. The darkly comedic story about a morbid and miserable young man consumed by his blue blood trappings and the nearly 80-year-old wild woman he falls in love with is as uplifting as it is heartbreaking. Harold’s obsessed with death, but learns to embrace life through Maude — one of the coolest manic pixie dream girls in cinematic history.
Some Like it Hot
Witnesses to a brutal crime escape the mob by hopping a train, dressing as women, and disguising themselves as members of an all-girl band. They take an immediate liking to the group’s singer and ukulele player — a curvy, blond bombshell named Sugar Cane (Marilyn Monroe). She becomes BFFs with the cross-dressing duo, and ends up falling for Joe/Josephine (Tony Curtis) despite his complicated stint with lipstick and high heels.
Eternal Sunshine of the Spotless Mind
Mismatched, sometimes toxic, usually adorable, and totally smitten with each other, Joel and Clementine (the talented Jim Carrey and Kate Winslet) bypass the expected cinematic odd couple cliches thanks to a poignant, surreal look at relationships through Michel Gondry and Charlie Kaufman’s eyes. Even better is that the film doesn’t rely on the crazy mind powers quotient to portray an honest look at opposites.
The Steve Martin acted/written/produced Roxanne is a reworking of the 1897 play Cyrano de Bergac as a romantic comedy. Daryl Hannah stars as the titular object of a large-nosed, but poetically inclined, man’s affections (Martin). Unfortunately, she falls for the local beefcake instead, but only due to being wooed by his love letters — which turn out to be written by mister nose. It’s the familiar love-is-all-the-same-on-the-inside stuff, but Martin makes it great.
The African Queen
Humphrey Bogart trades his debonair personality for that of a cocky captain with a love for the bottle in The African Queen. Meanwhile, his newfound traveling companion is a pearl-clutching goodie two-shoes (Katharine Hepburn). They escape the menace of wartime by sailing downriver and overcome the odds of their personalities, and dangerous adventures, by uniting as one.
Judd Apatow makes yet another movie about the nerdy schlub who gets the hot girl — this time Katherine Heigl and Seth Rogan … but only after he knocks her up.
The Millennium Trilogy
The often ambiguous relationship between hacker Lisbeth Salander and reluctant detective Mikael Blomkvist in the Millennium Trilogy has been exhaustively written about since the films’ popularity took off (including David Fincher’s recent remake). Does Lisbeth have a daddy complex? Are they the creation of author Steig Larsson’s unabashed sexual fantasies? Whatever your theory, the older man and younger woman seem to share a unique intimacy and understanding despite their vast visible differences.
The Fifth Element
All dissimilarities between a fearless taxi driver and a despondent humanoid hottie melt away when their kiss releases the powers of Divine Light and saves the planet. True love, indeed.
It doesn’t get much odder than making out with and murdering your own fractured, unhinged personality construct. Clearly this strange, pseudo love connection doesn’t end well for high-strung ballerina Nina Sayers in Darren Aronofsky’s Black Swan. Still, we’ll call it a match since her fling with “Lily” is necessary to achieve the dancer’s perceived state of perfection at the film’s end.
Scott Pilgrim vs. the World
Edgar Wright’s Scott Pilgrim vs. the World opts for a sweet and hilarious look at young men in love and the lengths they’ll go to woo the girl. We’ve heard some argue that it’s not far from the Judd Apatow comedic formula about geeky guys who get it all in the end, but we don’t recall an Apatow movie where the dude has to fight multiple crazy ex-boyfriends in an videogame-style arena of death — which means this pick has surely earned a spot on our list.