I have been watching a lot of romantic comedies to prepare for the rom-com site tour of the Upper West Side that I'll be leading, starting next week, with my friend and colleague, Erin Carlson. In fact, the origins of this tour go back a few months: I started thinking about this all-but-dead movie genre thanks to a confluence of influences, from The Mindy Project (which I recap for Vulture.com), to that piece in The Atlantic last year about why they suck so badly, to Linda Obst's book Sleepless in Hollywood (about the demise of the kind of film that Obst made her name producing). Then, Erin and I found ourselves spontaneously re-enacting the scene from You've Got Mail in which Tom Hanks and Dave Chappelle banter outside Cafe Lalo, on New York's Upper West Side, about Hanks's impending meeting with online love interest Meg Ryan.
If romantic comedies were once cool enough for even Dave Chappelle, what the hell has happened? Well, a zillion theories have been batted about, including my own thoughts about how confusing modern romance can be. But the fact remains that romantic comedies serve a purpose in life: They allow us to figure out what we want and don't want, what we need and don't need, from our romantic relationships. And, as I found out last week during a discussion about favorite rom coms with some other women, they allow us to tell our most intimate stories and bond in instantaneous ways, especially with other women. ("You cancelled a wedding? So did I! Here's what happened ...")
With all of that in mind -- plus the essential, ineffable qualities of the best rom coms, like chemistry and witty banter -- here are my personal favorites of that much-derided genre, chick flicks:
10. Serendipity: Totally silly movie, of course, and yet ... if anyone can make me believe in magical destiny, it's John Cusack and Kate Beckinsale here. They also made me believe in the inherent goodness of New York City and the power of a flipped bob haircut at a time when I needed it most, right after I moved to New York City with the wrong guy. I got that haircut, drank several frozen hot chocolates, and eventually found myself.
9. The Wedding Singer: Drew Barrymore is a slam dunk; Adam Sandler is not. Here, opposites attract, and an '80s soundtrack seals the deal. I happen to like Music and Lyrics, starring Barrymore and Hugh Grant (as, essentially, a washed-up Andrew Ridgeley type who'd lost his George Michael), though the chemistry isn't quite of the Hanks-and-Ryan level.
8. 10 Things I Hate About You: Some of our most reliable rom coms happen to also be teen movies. No coincidence: Teen characters have more license to act dumb and learn lessons. Here, we get an extra dose of Shakespeare's Taming of the Shrew, along with stellar performances from future stars Julia Stiles and Heath Ledger.
7. Knocked Up: The good news is that Judd Apatow reinvented romantic comedies to include male perspectives, too. The bad news is he reinvented them so well that people stopped caring about smart women in the one genre where they used to rule. Still, Apatow makes some funny-sweet movies.
6. Sex and the City: The movie version of the show launched a million girls-nights-out, and for good reason. Carrie and company delivered again, making for a nice do-over after the less-than-perfect series finale. Let's not talk about that second movie.
5. Easy A: Part of the fine tradition of high school rom coms, this one took the edge factor up a bit with its racy plot -- a girl pretends to bed various geek types to help them seem cool. The details are irrelevant when you realize this movie brought the world Emma Stone.
4. Clueless: The best high school movie of all time, period. Of course it was based on a Jane Austen plot.
3. Reality Bites: I can't judge this rationally. I'm a teen of the '90s. This shaped my entire world view.
2. Say Anything ...: I said Clueless was the best high school movie of all time. This may technically be about high schoolers, but it transcended such boundaries. "I gave her my heart and she gave me a pen." John Cusack. Boom box. Swoon.
1. When Harry Met Sally ...: Is there anything better? I'm lumping this in with its slightly lesser, but still amazing, counterpart, You've Got Mail, also written by Nora Ephron and a slobbery love letter to the romantic possibilities of Manhattan. Ephron is a goddess of perfect dialogue, and these two movies -- plus Sleepless in Seattle -- show that she knew on-screen chemistry like no one else. When Harry Met Sally and Say Anything ruined an entire generation for love by setting expectations astronomically high -- and by using random ellipses with abandon.