It didn’t take long for Natalie Portman to sink that great Black Swan buzz. In fact, all it took was No Strings Attached, a romantic comedy co-starring Ashton Kutcher about a friends-with-benefits couple who get serious. Why so cynical? Because romantic comedies kinda blow. More often than not, they’re made by greedy studios cashing in on two good-looking leads, tossed together with a formulaic script. But they’re not all Mr. Wrongs. Here are 10 romantic comedies that get it right.
1. Annie Hall (1977)
Woody Allen’s comedy is smart, sophisticated, and funny as hell. Allen plays … well, he plays himself, essentially, and he’s dating Diane Keaton’s title character, a bundle of ’70s neuroses who has relationship issues, a fear of spiders, and an anti-Semitic grandmother. Every romantic comedy should aspire to be half this good.
2. The Apartment (1960)
Jack Lemmon rents his apartment to his bosses so they can carry on affairs. He falls for Shirley MacLaine, one of the execs’ girlfriends. Director and co-writer Billy Wilder jabs at late-’50s ideals with a sharp wit. It takes a while for the romance to bloom, as Lemmon and MacLaine dance around their real feelings.
3. It Happened One Night (1934)
It’s a road trip movie that doubles as a romantic comedy. Frank Capra’s classic stars Claudette Colbert as a spoiled rich woman on the run who hooks up with Clark Gable, a reporter looking for a story. The familiar recipe — girl meets boy, girl hates boy, girl loves boy — starts here.
4. The Philadelphia Story (1940)
Katharine Hepburn is wooed by three guys, including her ex, Cary Grant. She’s a socialite who’s about to get married again; James Stewart is the reporter who crashes her nuptials. A fast, clever, and hilarious movie by George Cukor. The opening scene is one of the funniest ever filmed.
5. His Girl Friday (1940)
There’s a reason so many of the movies on this list were made before your mom was born: great, unpredictable writing. There’s no guarantee the main couple would live happily ever after. Newspaper editor Cary Grant tries to keep his best reporter (another one?) from getting married. She also happens to be his ex-wife.
6. Manhattan (1979)
He’s pretty much known now as the dirty old man who married his girlfriend’s adopted daughter. But back in the day Woody Allen was a master of modern-day relationships. This love quadrangle includes a 42-year-old divorced guy dating a high-school girl, his best friend’s mistress, and Meryl Streep as a lesbian.
7. Harold and Maude (1971)
Talk about robbing the cradle. Depressed teen Harold (Bud Cort) spends his spare time hanging out at funerals. He meets 79-year-old Maude (Ruth Gordon) at one of them, and they begin a relationship. This counterculture classic broke down tons of barriers. It still holds up.
8. When Harry Met Sally … (1989)
Everyone knows the deli scene (yeah, yeah, we’ll have what she’s having too … ), but Rob Reiner’s smart, sly love story is packed with funny lines. It’s one of the rare movies where you hope the platonic, lifelong best friends actually hook up in the end. Meg Ryan was never cuter.
9. High Fidelity (2000)
Nick Hornby’s beloved book is a music geek’s wet dream, filled with Top 10 lists and adorably cool girls. The movie version is almost as good. John Cusack plays an obsessive record-store owner who augments his tales of busted relationships with tragically hip soundtracks.
10. The 40 Year Old Virgin (2005)
He may not want to admit it, but Judd Apatow makes chick flicks. And really funny ones at that. This one gets the nod over Knocked Up because it has a bigger heart and more laughs. Stellar cast too, including Steve Carell, Catherine Keener, Paul Rudd, and Seth Rogen. •