16. Midnight in Paris
With Midnight in Paris, Woody Allen all but remade his own Purple Rose of Cairo, his classic cautionary tale about the perils of nostalgia. Owen Wilson’s Gil literally gets stuck in the past, finding a portal in the streets of Paris to the France he idealizes. Despite the overt romantic subplot, Allen’s real love letter is to the city itself, one he idealizes as much as Gil. Even as our romances become myths, the worlds we construct around us, some ideals are worth savoring.
Cher’s Oscar-winning performance benefits from a lively screenplay by John Patrick Shanley, finding the balance between cynicism and hopefulness. An Italian-American widow (Cher) meets another man (Nicolas Cage) as she’s about to become engaged, whose passion challenges her in a way she’s not used to. What’s interesting, though, is that the movie shows us what’s it’s like to be in love when you know better, when you’re too smart to fall head over heels. It’s about the loves we resist and that won’t go away, no matter how hard we push back.
18. My Big Fat Greek Wedding
My Big Fat Greek Wedding made a killing in 2002, still the highest-grossing rom-com ever made. There’s a reason. Nia Vardalos’ script (based off her stage play) is as clunky as it is hilariously relatable, finding the universal in her “crazy” Greek family. Vardalos’ family is everyone’s family, except that they eat more lamb. The film also gets the best possible use out of Sex and the City’s John Corbett, as the long-haired suitor who challenges her family’s traditional ways.
19. Punch-Drunk Love
Adam Sandler’s best movie is one of the darkest romantic comedies ever made, serving both as a deconstruction of Sandler’s career and yet another triumph from auteur P.T. Anderson. Sandler plays a fucked-up guy soul who finds his match in Emily Watson, who might be more twisted than he is. Like Harold and Maude, Punch-Drunk Love is anything but your typical romantic comedy. It’s better. Take this exchange for example:
Barry (Sandler):“I’m lookin’ at your face and I just wanna smash it. I just wanna fuckin’ smash it with a sledgehammer and squeeze it. You’re so pretty.”
Lena (Watson): “I want to chew your face, and I want to scoop out your eyes and I want to eat them and chew them and suck on them.”
You won’t find that in a Katherine Heigl movie.
20. Say Anything…
John Cusack’s most iconic role is the movie that made Cameron Crowe’s career. Cusack plays Lloyd Dobler, who meets the right girl at the wrong time. Diane Court is the girl you dream about meeting — smart and driven — and Dobler finally gets her right before she’s about to start a whole new life in London after their high school graduation. Say Anything… shows that the loves were meant to lose might be as important as the ones that last.