How ‘When Harry Met Sally’ Created the Modern Rom-Com

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Like them or not, the romantic comedy genre is a powerful one and all modern rom-coms can trace their roots back to one film: When Harry Met Sally.

This genre has also become very lucrative. It’s the reason studios will always turn to the Rom-Com: they’re inexpensive to make, have a quick turnaround time, and always make money. 

Romantic comedies are the seventh highest-grossing film genre. That may seem lower down the list, but as of 2021, this genre has made over $10 billion. And most notably: this is based on only 625 films. Compare this to the drama category. Dramas have generated around $35 billion, but that’s based on over 5,400 movies. 

When you break the stats down per movie, rom-coms make an average of about $15 million each, whereas a drama averages just $6.5 million per film. Financially, rom-coms are often the better bet. 

It’s not that rom-coms weren’t a thing before 1989, it’s just that When Harry Met Sally perfected the model. It’s a collaborative effort between the great Nora Ephron and Rob Reiner and almost serves as a biographical film as much of the movie’s content comes from their real lives.

When Harry Met Sally was a massive critical and commercial hit when it came out in 1989, and the rom-coms you still watch to this day continue to borrow from its perfect execution.

It’s also a love letter to New York, made Meg Ryan and Billy Crystal even bigger stars, and features a lot of the brilliant improvising of Crystal which also helped to shape the film.

Let’s do a quick recap of the movie, a look at how this thing came together, and how it solidified the massive genre that is rom-com.

The Plot of When Harry Met Sally

We start in 1977 when a young Sally Albright meets a “young” Harry Burns. I always find it hilarious how Crystal and Ryan are supposed to be college students. Meg Ryan might pass, but Billy Crystal, with his hilarious hair and sideburns, looks more like the school groundskeeper.

Ryan has a pretty feathered out Farrah Fawcett hairdo and the idea with her hairstyles was that they would get progressively younger-looking as she got older.

Harry was dating one of Sally’s friends, and both are heading to New York, so they decide to share the driving duties. Harry immediately establishes himself as a classic dirtbag. He states that men and women can never be friends and this established the entire premise of the movie.

Sally turns out to be high maintenance, Harry makes a pass at her, and they have to survive the uncomfortable 18 hour trip from Chicago to New York. They end up by Washington Square Park and go their separate ways.

Cue five years later and Sally is making out with her boyfriend Joe (played by the son of President Gerald Ford). Harry sees them but recognizes only Joe. Then, on the plane, they realize they know each other. 

Again, they go their separate ways. Another five years pass and they run into each other in a bookstore. Sally is with her hopelessly single friend Marie, played by the beloved Carrie Fisher. The two reconnect and they find out that each is now single. 

They start to hang out, spending a lot of time together and nights talking on the phone. They took this from Reiner’s life when he was going through a divorce. He would spend the nights talking to friends on the phone to get him through his despair.

At a New Year’s Eve party, Harry and Sally discover they are attracted to each other but try to squash it by setting up each other with their friends. Their friends end up getting together and eventually marry.

Then Harry and Sally hook up when he tries to comfort her. This blows up in their faces and they realize they’ve ruined the friendship. Sally avoids Harry until they have to confront each other at Marie’s wedding. All looks lost until Harry professes his love to her at a New Year’s party and they live happily ever after.

Fun fact: the first draft of the script didn’t have them getting together. 

How Did This Movie Come Together?

When Harry Met Sally really is the tale of Rob Reiner and Nora Ephron. Reiner was going through a divorce and this is reflected in the hopelessness and depression of Harry. Sally is a combination of Ephron and friends of hers that also were experiencing the same issues with singleness.

The two met to hash out the idea for this movie, and most of what you see are the same words and situations that happened to them. If you watch the DVD commentary for the movie, you get great insights into how this came together.

Bringing in Billy Crystal was instrumental in the movie’s direction as he helped to shape more of the tone and comedy. He also added a lot to the scenes and this—and his brilliant improvising—helped create the movie we know love.

The movie would tell their story was also being interspersed with couples telling their own love stories. I always thought these were genuine couples but were actually actors telling real-life stories. These actors perfectly captured the awkwardness and unnaturalness that comes from real people speaking on camera.

As mentioned, this movie is a love letter to New York, and they based the film there. I love that it features all the different seasons. I also love that it doesn’t use all the cliche locations we expect with an NYC-based movie. Reiner said that he believed Woody Allen had covered every inch of the city and he didn’t want to film in locations that Allen had already captured.

Before Billy Crystal came on board, they offered the role of Harry to Tom Cruise, Michael Keaton, Richard Dreyfuss, Tom Hanks (obviously), and Albert Brooks. Brooks also made comparisons to Woody Allen and thought it would be too similar to his work.

For the role of Sally, Reiner originally wanted Susan Dey, who starred in the Partridge Family. Before Meg Ryan came on, they also considered Molly Ringwald.

Some Great Behind the Scenes Facts

There are a lot, and most involve Billy Crystal, but here are some cool things you may have not known about the movie.

  • The famous scene in Katz’s Delicatessen has become an iconic film moment. The idea to set it in a public setting was Meg Ryans. Rob Reiner’s mother performed the line “I’ll have what she’s having”. Billy Crystal had come up with the line on the spot and they used it in the movie and became one of the funniest of all time
  • There’s an actual Easter egg in this movie. In the scene where Harry is sitting in the bookstore reading by himself, he’s reading the book “Misery” by Stephen King. This was the next project that Reiner would work on, and he planted this little clue in the film
  • The “poppycosh” scene in the library was, again, totally improvised on the spot by Billy Crystal. Meg Ryan knew to just roll with his spontaneity, but in the scene, you can actually see her look off-camera to Reiner to wonder if she should keep going with it
  • The original title was going to be called “How They Met.”
  • Billy Crystal kept himself separate from the cast and crew to get into the mode of feeling isolated and alone
  • The four-way telephone scene took over 50 takes until they got a usable one
  • The Pictionary scene and the end interview with Harry and Sally were both completely improvised
  • Here’s a bizarre one, but this movie has been noted as driving more people to drink bottled water. This really wasn’t a thing in the late 80s, but you’ll notice that Sally is always carrying and drinking from bottled water

The Importance of the Soundtrack to When Harry Met Sally

We now all know the great Harry Connick Jr, but this wasn’t the case in 1989. This blew my mind, but he was only 20 years old when he was brought in to create the music for the movie. A friend of Reiners recommended him. 

The film makes great use of big band/swinging jazz, which creates an upbeat atmosphere throughout most of the film. Connick Jr. was also used because of his unique voice. Not only did he have incredible musical ability, but Reiner thought he sounded like Frank Sinatra.

The film also made use of classic American standards sung by Louis Armstrong, Ella Fitzgerald, Sinatra, and Bing Crosby. It’s not that some of these standards hadn’t been used before, but When Harry Met Sally used them in a way that comedies really hadn’t before.

Again, these types of songs are now go-to choices for romantic comedies, and they have their roots in this film. The song “It Had to be You” is the cornerstone of the movie and is woven throughout the entire film. Other popular hits include:

  • Love is Here to Stay 
  • Don’t Get Around Much Anymore
  • Autumn in New York
  • Let’s Call the Whole Thing Off

Fun fact: the soundtrack ended up hitting number one on the Billboard jazz charts. 

The Success of When Harry Met Sally and How This Affected the Rom-Com Genre

When Harry Met Sally came out on July 14, 1989. And it was a gigantic hit. Columbia Pictures was so sure they had a hit on their hands that they slowly released it knowing that word-of-mouth was going to help in its success.

And it did. The movie was a critical hit, and audiences ate it up. On just a budget of $16 million, When Harry Met Sally made nearly $100 million. Converted for today, this is more than $205 million.

This was pretty shocking for the movie industry that a “romantic comedy” could bring in this type of money.

When Harry Met Sally was technically more of a comedy than a rom-com, as that word wasn’t necessarily part of the public lexicon yet. 

Not just movies but TV series and it established the high maintenance, difficult girl and the idea of the transitional boyfriend/girlfriend. Countless films and shows have used this premise ever since, along with using a similar soundtrack. Here’s just a few:

  • You’ve Got Mail
  • Sleepless in Seattle
  • Forget Paris (a very unknown and super underrated rom-com also starring Billy Crystal)
  • My Best Friend’s Wedding
  • The Wedding Planner
  • Maid in Manhattan
  • Pretty much everything on the Hallmark channel
  • While You Were Sleeping
  • Bridget Jones’ Diary
  • Notting Hill
  • 50 First Dates
  • The Proposal
  • Always be My Maybe

That’s just a small sampling of movies, but we can feel the impact of When Harry Met Sally throughout shows like Sex and the City, and even the first few seasons of Seinfeld. 

Final Thoughts on When Harry Met Sally

This movie works, and it’s lasted because the main ideas are timeless. Men and women will always have issues with how they relate. Every generation will wonder if they can “just be friends,” and there will always be the issue of sex getting in the way.

Reiner states that they also focused the movie on how friendship needs to be at the core of a genuine relationship. Again, these issues will always remain, and that’s what makes this film so timeless. 

You could play this movie 200 years from now, and these issues will still be dealt with even if we’re living underwater or on the moon. It’s as contemporary as contemporary can be and the only thing that dates it is the hairstyles and lack of cell phones. 

When Harry Met Sally has cemented itself as not just a great rom-com, but an important Hollywood film. It shows up on countless top ten lists for not just rom-coms, but comedies, and helped to cement a new—and incredibly lucrative—genre of film. 

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