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The romantic comedy has the toughest job of all movie genres: It must be both romantic and funny without overdosing on sweetness, and still manage to seem completely effortless so that the audience will believe the sparks flying between those mismatched leads. Making a good one is impossible if just one element is off, but the ones that click become love stories for the ages. Here are the ten your grandchildren will be watching with their future spouses.
10. The Princess Bride (1987)
Many romance comedies play like fairy tales, but few really are. One exception: The Princess Bride, a chivalrous yarn born out of a bedtime story. Filled with pirates, magicians, and revenge-seeking swordsmen, the heart of its story concerns a farm boy who tries to rescue a beautiful young woman engaged to a boorish prince against her will. With a nod to the medieval tall tales of yore, The Princess Bride appeals to the lovestruck child in all of us.
9. The Shop Around the Corner (1940)
Before the Internet age and You've Got Mail, there was the original comedy of anonymity and mistaken identity, The Shop Around the Corner. Starring James Stewart and Margaret Sullivan as co-workers with an intense mutual antipathy, they fall in love, but with a twist -- they meet via pen pal correspondence without realizing it's the other to whom they're writing. Hilarious and frustrating, the movie demonstrates that sometimes, true love can be found right next to you.
8. Say Anything (1989)
"If you guys know so much about women, how come you're here at, like, the Gas 'n' Sip on a Saturday night completely alone?" There will never be a shortage of teen romantic comedies, but the ones that matter can be counted on a single hand, and Cameron Crowe's intelligent and endlessly entertaining Say Anything -- about a slacker who woos the
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class valedictorian -- leads the pack. It's the rare teen comedy that takes its demographic seriously while indulging their romanticism. Was there ever a cooler underachiever than John Cusack's boombox-wielding boyfriend?
7. Sleepless in Seattle (1993)
Sure, it's a chick flick, but Sleepless in Seattle seems to transcend typical gender tastes. Meg Ryan (of course) plays an attached but unhappy woman looking for love, finding it in the form of Tom Hanks' everyman widower. If ever a movie worked with the idea of fate, this is it, each moment (the radio call-in show, the fan letter that reaches Hanks, the meeting on the Empire State Building) is based on a one-in-a-million coincidence, and gives us all hope in the possibility of successful chance encounters.
6. Roman Holiday (1953)
Not all romantic comedies must end happily, and Roman Holiday proves this can be done without cheating the audience. Reporter Gregory Peck encounters a princess playing hooky, Audrey Hepburn, in the role that won her an Academy Award and made her a star. Their time exploring the city together is an idyllic vacation, all the more perhaps because the demands of their lives beyond Rome propel them to make the best of it. In the end, the audience sighs as well as swoons.
5. Eternal Sunshine of the Spotless Mind (2004)
Ever been so in love and yet so angry with someone that you just wanted to get them out of your head? Screenwriter extraordinaire Charlie Kaufman and visionary director Michel Gondry explored the possibilities of just that in Eternal Sunshine. Jim Carrey's mopey protagonist goes through his own mind as it's erased, trying to hide his cherished memories of his beloved Kate Winslet. Mixing remembrances and fantasies and hilariously playing with time, Eternal Sunshine suggests love goes straight to the heart and not to the head.
4. When Harry Met Sally (1989)
Can men and women just be friends? That's the question that leads to a wildly mixed answer and the much-delayed romance of the title couple: Billy Crystal's sex-only Harry and Meg Ryan's friends-forever Sally. A more upbeat version of Woody Allen's Manhattan-bound battle of the sexes, When Harry Met Sally describes a realistic trajectory of romance from denial to love, embellished by some of the funniest scenes in film history. And yes, that starts with Ryan's fake orgasm.
3. His Girl Friday (1940)
With Bringing Up Baby, director Howard Hawks patented his screwball formula, and in His Girl Friday he may have perfected it. Cary Grant and Rosalind Russell are the former lovers and former colleagues whose rapid-fire give-as-good-as-they-get repartee masks an unmistakable passion that must be rekindled. The tough-talking Russell is throwback to a time when women weren't just desperately doing the chasing (as with He's Just Not That Into You), but active participants in a courtship.
2. It Happened One Night (1934)
The spoiled rich girl. The rough and tumble reporter. They couldn't be more different, and yet they -- especially the girl, brought down to the real world for the first time -- find they couldn't be more in love. It's a formula that's worked for seemingly ever, but Clark Gable and Claudette Colbert defined it in Frank Capra's screwball classic It Happened One Night, considered risque for its time with its characters' talk of breaking down "the walls of Jericho" and Colbert's skirt-raising hitchhiking scene.
1. Annie Hall (1977)
Woody Allen's comedic masterpiece of unrequited love and neurosis so transcended its genre, it won a Best Picture Oscar, the last (intentional) comedy, and certainly the last romantic comedy, to do so. Overflowing with innovation (animated interludes; subtitles showing us what Allen's Alvy and Diane Keaton's lighthearted Annie are thinking) and compassion for the two flawed characters, Allen's movie is an ode to many things, including the power of movies to make us laugh while breaking our hearts.
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