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Readers’ Poll: The 10 Best Romantic Comedies

See what film managed to top ‘Say Anything,’ ‘Annie Hall’ and ‘The Wedding Singer’

Meg Ryan and Billy Crystal

WHEN HARRY MET SALLY..., Meg Ryan, Billy Crystal, 1989. (c) Columbia Pictures/ Courtesy: Everett Collection.

©Columbia Pictures/Everett Collection

Fifty Shades of Grey made an astonishing $93 million during the extended Valentine's Day weekend, shattering many records in the process. It wasn't marketed as a comedy and the filmmakers certainly didn't intend to make audiences laugh, but many critics reported chuckles throughout the theater at moments meant to be deadly serious. The whole premise is a little goofy and it got us thinking about romantic comedies, so we asked our readers to vote for their favorite ones. Here are the results. 

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WHEN HARRY MET SALLY..., Meg Ryan, Billy Crystal, 1989. (c) Columbia Pictures/ Courtesy: Everett Collection.

©Columbia Pictures/Everett Collection

10

‘There’s Something About Mary’

The Farrelly brothers reached the apex of their success with his hysterical 1998 film about a man unable to get over his teenage crush. It turned Cameron Diaz into a genuine superstar and helped Ben Stiller get over the commercial debacle of The Cable Guy, grossing an astonishing $369 million. For months on end people couldn't stop talking about Mary's mentally handicapped brother, the heinously injured dog and that immortal scene where Cameron Diaz puts semen into her hair thinking it's hair gel. The stuff with the brother might not fly these days, but 1998 was a more innocent time. The Farrelly brothers never managed to create another cultural sensation like this, but they keep trying. 

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WHEN HARRY MET SALLY..., Meg Ryan, Billy Crystal, 1989. (c) Columbia Pictures/ Courtesy: Everett Collection.

©Columbia Pictures/Everett Collection

9

‘Notting Hill’

A soft-spoken, British bookstore owner has an unexpected meeting with the most famous actress on the planet and the two fall madly in love, though they're torn apart once the media learns about their relationship. It's a great premise for a romantic comedy, and it's impossible to imagine better casting than Julia Roberts and Hugh Grant. Nobody plays glamorous like Roberts and Grant has made a great career out of playing slight variations of this exact same character. The film grossed $364 million and it even managed to impress the critics. 

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WHEN HARRY MET SALLY..., Meg Ryan, Billy Crystal, 1989. (c) Columbia Pictures/ Courtesy: Everett Collection.

©Columbia Pictures/Everett Collection

8

‘Eternal Sunshine of the Spotless Mind’

Charlie Kaufman has a truly unique brain. Who else could have dreamed up movies as brilliantly mind-bending as Being John Malkovich, Adaptation and Synecdoche, New York? He's also responsible for Eternal Sunshine of the Spotless Mind, a 2004 Jim Carrey/Kate Winslet movie that only seems to get more popular as times goes on. The two of them play a former couple that erased their memories of each other, but somehow continue to meet again and again. It was the culmination of a rather amazing decade of Jim Carrey movies that began with Ace Ventura: Pet Detective

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WHEN HARRY MET SALLY..., Meg Ryan, Billy Crystal, 1989. (c) Columbia Pictures/ Courtesy: Everett Collection.

©Columbia Pictures/Everett Collection

7

‘You’ve Got Mail’

You've Got Mail hit theaters just two years before the turn of the millennium, but it feels much, much older when you watch it today. It was an era of dial-up modems, enormous bookstores chains that engulfed neighborhoods and Meg Ryan as a leading lady. Tom Hanks plays an executive at Fox Books, a Borders-type chain that's threatens to drive Meg Ryan's tiny children's bookstore out of business. They despise each other in real life, but fall in love when they meet in an AOL chatroom. It wrapped up the trilogy of Meg Ryan/Tom Hanks movies that began with Joe Vs. The Volcano and continued with When Harry Met Sally. 

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WHEN HARRY MET SALLY..., Meg Ryan, Billy Crystal, 1989. (c) Columbia Pictures/ Courtesy: Everett Collection.

©Columbia Pictures/Everett Collection

6

’50 First Dates’

Six years after they teamed up for The Wedding Singer, Adam Sandler reunited with Drew Barrymore for another romantic comedy. This time around, Barrymore played a woman that suffers from amnesia due to a car accident. Every morning she wakes up, all memories of the previous day are totally erased, which makes it a little tricky for Adam Sandler to pull of a successful courtship. All sorts of wackiness ensues, but he eventually stumbles upon a way to make their relationship function. The film grossed $196 million despite pretty shaky reviews. When they teamed up last year for Blended, however, that Sandler/Barrymore magic seemed to have finally run out. 

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WHEN HARRY MET SALLY..., Meg Ryan, Billy Crystal, 1989. (c) Columbia Pictures/ Courtesy: Everett Collection.

©Columbia Pictures/Everett Collection

5

‘Say Anything’

Peter Gabriel has accomplished many great things since Genesis first hit the scene in the late 1960s, but for people of a certain age his legacy all comes down to a single moment in the 1989 Cameron Crowe movie Say Anything. The scene comes near the end when John Cusack demonstrates his love for Ione Skye by standing outside her window and holding up a boombox playing Peter Gabriel's "In Your Eyes." He was a slacker, she was a valedictorian and their lives were headed in different directions, but they just can't seem to break apart. The "In Your Eyes" scene brought tears to many teenage girls that wore out their VHS copies of the movie, and Cusack even recreated it at a Gabriel concert a few years ago. 

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WHEN HARRY MET SALLY..., Meg Ryan, Billy Crystal, 1989. (c) Columbia Pictures/ Courtesy: Everett Collection.

©Columbia Pictures/Everett Collection

4

‘Love Actually’

Most romantic comedies focus on a single couple, while an ambitious one tries to tackle two relationships. 2003's Love Actually goes for broke delving into about a dozen relationships over the course of two hours and nine minutes. That's way too much for plot for most screenwriters, but Richard Curtis is the man behind Notting Hill, Four Weddings and a Funeral and Bridget Jones's Diary, making him almost uniquely capable to helm such a project.  The film takes place shortly before Christmas as couples fight, break up and ultimately find true love. The cast is absolutely huge, featuring everyone from Liam Neeson to Emma Thompson to Colin Firth and Rowan Atkinson. 

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WHEN HARRY MET SALLY..., Meg Ryan, Billy Crystal, 1989. (c) Columbia Pictures/ Courtesy: Everett Collection.

©Columbia Pictures/Everett Collection

3

‘The Wedding Singer’

The 1980s were just nine years prior to when The Wedding Singer arrived in theaters, but it already seemed like a distant past well worth mocking. After all, what looks more ridiculous today than Flock of Seagulls haircuts, Miami Vice beards and early Billy Idol videos? In the movie, Adam Sandler plays a popular wedding singer and Drew Barrymore plays a waitress at the ballroom where he regularly performs. It begins with them promised to other people, but when he's left at the altar and her boyfriend reveals himself to be a huge douche, they eventually come together. 

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WHEN HARRY MET SALLY..., Meg Ryan, Billy Crystal, 1989. (c) Columbia Pictures/ Courtesy: Everett Collection.

©Columbia Pictures/Everett Collection

2

‘Annie Hall’

No filmmaker has created more great romantic comedies than Woody Allen, but there's something about Annie Hall that seems to stand out above all the others. The 1977 film won Best Picture at the Academy Awards, which is almost unheard of for any sort of comedy, romantic or otherwise. Allen plays Alvy Singer, a Jewish comedian struggling with the aftermath of his relationship to the Waspy Annie Hall. The film originally contained an entire murder mystery plot that was dropped until Allen revived it for 1993's Manhattan Murder Mystery

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WHEN HARRY MET SALLY..., Meg Ryan, Billy Crystal, 1989. (c) Columbia Pictures/ Courtesy: Everett Collection.

©Columbia Pictures/Everett Collection

1

‘When Harry Met Sally’

Early on in When Harry Met Sally, Billy Crystal tries to explain to Meg Ryan why men and women can't truly be friends. "No man can be friends with a woman that he finds attractive," he says. "He always wants to have sex with her." Ryan asks about a woman that a man finds unattractive. "No," he says.  "You pretty much want to nail 'em too." The couple spends the rest of the movie trying to disprove the theory, but they ultimately wind up in bed and find their friendship ruined as a result. Needless to say, they're together by the last frame of the movie. 

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