When Harry Met Sally 5 Reasons Its The Greatest RomCom Ever Made (& Its 5 Closest Contenders)

When Harry Met Sally: 5 Reasons It’s The Greatest Rom-Com Ever Made (& Its 5 Closest Contenders)

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When Harry Met Sally set a high benchmark for the romantic comedy genre when it hit theaters in 1989; it still has yet to be topped.

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When Harry Met Sally 5 Reasons Its The Greatest RomCom Ever Made (& Its 5 Closest Contenders)

From the minds of director Rob Reiner and screenwriter Nora Ephron, When Harry Met Sally set a high benchmark for the romantic comedy genre when it hit theaters in 1989. It still has yet to be topped, and it’ll take quite a movie to dethrone it. Recent genre offerings like Yesterday and Last Christmas won’t cut it.

It’s easy to dismiss the rom-com as a flashy product of factory-line Hollywood manipulation, but there’s a lot of potential in a humorous love story mixing comedy and romance. There have been plenty of great rom-coms, both before and after When Harry Met Sally’s release.

10 When Harry Met Sally Is The Best: Billy Crystal And Meg Ryan Are Perfectly Matched

When Harry Met Sally 5 Reasons Its The Greatest RomCom Ever Made (& Its 5 Closest Contenders)

Performances and casting aren’t necessarily the most important element of every movie. Stanley Kubrick’s 2001: A Space Odyssey, for example, relies more on its groundbreaking visual effects and mind-boggling philosophical musings than its stars. But actors can make or break a romantic comedy.

Well-matched leads are the key to any great rom-com. When Harry Met Sally’s leading duo, Billy Crystal and Meg Ryan, are both individually perfect for their roles and share fantastic on-screen chemistry.

9 Closest Contender: Four Weddings And A Funeral

When Harry Met Sally 5 Reasons Its The Greatest RomCom Ever Made (& Its 5 Closest Contenders)

In any discussion of rom-coms, the name Richard Curtis is bound to come up. He has written, and occasionally directed, some of the most popular rom-coms ever made, from Notting Hill to Love, Actually.

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His most well-crafted script is arguably his Oscar-nominated screenplay for Four Weddings and a Funeral, whose episodic structure was inspired by real-life weddings attended by Curtis, leading to inspired, relatable comedic material that’s rarely found in romantic comedies.

8 When Harry Met Sally Is The Best: It’s Idiosyncratic, But Universal

When Harry Met Sally 5 Reasons Its The Greatest RomCom Ever Made (& Its 5 Closest Contenders)

Nora Ephron’s near-perfect screenplay for When Harry Met Sally has the idiosyncratic wit of a Woody Allen script, but where Allen’s humor can often be alienating or oversophisticated, When Harry Met Sally is consistently accessible and universal.

The snappy back-and-forths in the dialogue, whether it’s been couples or friends or complete strangers, have a delightfully Seinfeldian quality.

7 Closest Contender: Groundhog Day

When Harry Met Sally 5 Reasons Its The Greatest RomCom Ever Made (& Its 5 Closest Contenders)

Drawn from one of the greatest screenplays ever written, Groundhog Day finds curmudgeonly news reporter Phil Connors, played by Bill Murray, living the same day over and over again.

The story begins to take shape as he realizes he’s in love with his producer Rita Hanson, played by Andie MacDowell, and uses his endless do-overs to figure out the perfect way to woo her. The high-concept premise is used as an engine to push Phil to grow as a person in a way that few male romantic leads do.

6 When Harry Met Sally Is The Best: The Characters Feel Real

When Harry Met Sally 5 Reasons Its The Greatest RomCom Ever Made (& Its 5 Closest Contenders)

There have been so many romantic comedies, and so many that follow the same well-worn story structure and character archetypes, that it’s rare for any rom-com characters to feel like real people. But Harry and Sally do feel like real people.

Harry has plenty of flaws, uses humor as a defense mechanism, and really grows following the misery of his divorce. Sally, on the other hand, is high-maintenance without being a “type.” She’s adorkable, but stands up for herself enough to avoid falling into Manic Pixie Dream Girl territory.

5 Closest Contender: His Girl Friday

When Harry Met Sally 5 Reasons Its The Greatest RomCom Ever Made (& Its 5 Closest Contenders)

Howard Hawks’ His Girl Friday is the ultimate screwball comedy. One of the earliest examples of a gender-swapped remake, it follows a newspaper editor who goes to extreme lengths to keep his reporter ex-wife from remarrying.

The script by Charles Lederer and an uncredited Ben Hecht has beautifully rhythmic dialogue, which is delivered with gusto by Cary Grant and Rosalind Russell.

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4 When Harry Met Sally Is The Best: It Popularized A Bunch Of Romantic Concepts

When Harry Met Sally 5 Reasons Its The Greatest RomCom Ever Made (& Its 5 Closest Contenders)

The core idea at the heart of When Harry Met Sally is the question of whether or not heterosexual men and women can just be friends. The fact that Harry and Sally end up falling in love suggests that the film’s stance is that, no, they can’t. But the movie brings a number of other factors into play.

It popularized such romantic concepts as being high-maintenance and dating a “transitional” person between relationships, which remain a staple of both the genre and discussions of real-life romance today.

3 Closest Contender: Annie Hall

When Harry Met Sally 5 Reasons Its The Greatest RomCom Ever Made (& Its 5 Closest Contenders)

Talking about Woody Allen is difficult with everything that’s come to light about the guy over the years, but as far as cinematic blends of romance and comedy go, Annie Hall is as perfect as they come.

Loosely structured more like a standup set than a traditional plot, Annie Hall boldly sets itself apart by opening with the announcement that the couple at the center of the story won’t end up together.

2 When Harry Met Sally Is The Best: It’s A Timeless Gem

When Harry Met Sally 5 Reasons Its The Greatest RomCom Ever Made (& Its 5 Closest Contenders)

While a lot of rom-coms have aged horribly since their release, like Never Been Kissed and Rumor Has It, the humor in When Harry Met Sally is timeless. The movie can be enjoyed just as much today as it was back in 1989.

The film’s attitude toward gender roles is surprisingly progressive, perhaps as a result of a male director working closely with a female screenwriter, and it’s not afraid to let its male lead express emotions.

1 Closest Contender: Roman Holiday

William Wyler’s Roman Holiday, one of the finest masterpieces in the history of American cinema, set the initial benchmark for the Hollywood rom-com. Audrey Hepburn and Gregory Peck are an on-screen pairing for the ages as a disillusioned princess and a reporter.

Shot on location in Rome at the height of the “Hollywood on the Tiber” era, Roman Holiday mixes witty dialogue (courtesy of screenwriting legend Dalton Trumbo) with gorgeous cinematography capturing the beauty of its Italian setting.

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