Can men and women be friends without romance screwing everything up? That’s the central question of When Harry Met Sally, the perfect romantic comedy starring Billy Crystal and Meg Ryan.
Grab a pastrami sandwich and see if you know some of these fascinating behind-the-scenes facts about this classic feel-good movie.
Real life dramatically changed the original ending
Director Rob Reiner, known for classics like The Princess Bride, had just gotten divorced from filmmaker Penny Marshall. With When Harry Met Sally, he wanted to explore his cynicism about love. So, the original ending wound up with the title characters not getting together.
Then, during production, a crew member introduced Reiner to photographer (and future wife) Michele Singer. He fell in love so hard that he changed the ending, having Harry and Sally stay together after all. Reiner and Billy Crystal wrote new dialogue for the final scene to make it make sense.
Actual royalty attended the film’s premiere
In 1989, the film premiered in London with a special guest in the audience: Princess Diana. Even with the film’s raunchiness, Lady Di had a blast, telling Crystal, “I’d be laughing a lot more, except I know everybody’s looking at me.”
Crystal actually joked with the famous member of the Royal Family. When the Princess said she was going to take her shoes off for the screening, Crystal said he was going to take off his pants! Princess Di even asked Reiner for a VHS copy to watch with her friends.
The film’s writer nearly toppled Newsweek
In 1962, recent college grad and aspiring writer Nora Ephron applied to Newsweek. But they only offered her a job as a mail girl, because they refused to hire female writers. For Ephron, that injustice simply could not stand.
Alongside many other female Newsweek workers, Ephron joined a class-action lawsuit against the magazine. They sued for discrimination based on gender, arguing that women can and should be allowed to write. The incredible case was adapted into an Amazon TV show, Good Girls Revolt.
This was just the beginning for Nora Ephron
After the success of When Harry Met Sally, Ephron wanted more. And she wound up directing her own material, making other romcom classics like Sleepless In Seattle and You’ve Got Mail. Clearly, Ephron and Meg Ryan are the dynamic duo we need but don’t deserve.
Anyone who worked with Ephron loved her. Ryan recalled the first time she read When Harry Met Sally: “I remember reading the script in like 40 minutes. It’s a fast, funny, hilarious read and there’s a type of music to it.” Sadly, Ephron died in 2012 at age 71.
Harry and Sally were almost played by different people
It’s hard to imagine Harry and Sally being played by anyone but Crystal and Ryan. But the studio’s first choices for Harry included Albert Brooks, Tom Hanks, and Michael Keaton. Keaton was busy that year with another little movie called Batman.
For Sally, Reiner and the studio looked at a wide variety of actresses, including L.A. Law star Susan Dey, Elizabeth Perkins, Once Upon a Time in America’s Elizabeth McGovern, and Brat Pack sensation Molly Ringwald. But you know what? If it ain’t Ryan, we’re dyin’.
Sesame Street produced a parody version
When Harry Met Sally is an R-rated comedy about romance, sex, and adults having conversations on nice furniture. In other words, the perfect subject matter for a parody from Sesame Street! Their segment, “When Cookie Met Sally,” is maybe even more charming than the film itself.
Cookie Monster loves cookies too much. Sally (an incredible Muppet likeness of Ryan) only eats cookies in moderation. Will these two ever get along? The answer is, “of course, and Cookie Monster learns a valuable lesson.” Maybe Crystal and Oscar The Grouch can play BFFs in a sequel.
Your favorite moments were straight up copied from Reiner and Ephron’s life
It’s simple: Rob Reiner is Harry and Nora Ephron is Sally. Thus, the screenplay was written by just typing out real life. Remember Sally’s hard-to-follow, “high maintenance” orders? That’s precisely how Ephron orders food. She just wants it the way she wants it!
To get in the mindset of the pessimistic Harry, Ephron interviewed Reiner about his disastrous love life. As he told The AV Club, “She was like a reporter, and I told her all these stories of different things that I had been through. And she wrote this stuff down.”
The interview stories came from real people
Remember the adorable stories couples tell about how they met? Those are all real. Ephron broke up writing sessions by interviewing real members of the production company about how they met their spouses. She and Reiner knew they would make perfect mini-scenes.
So, they went to work polishing and rewriting those stories. Then, they hired actors to play just the out-and-out cutest couples you’ve ever seen. Forget an anniversary gift — seeing your darling stories on the silver screen must’ve been more than enough joy for a lifetime.
Billy Crystal and Rob Reiner were real life best friends
Apart but together, Harry and Sally spend lots of time calling each other on the phone and watching TV. This, like many details, was inspired by Crystal and Reiner’s actual friendship. The two pals would do this in real life, which is actually the cutest thing ever.
Crystal said it was easy to get into character for Harry — he was already witnessing Reiner’s divorce firsthand. But that wasn’t the only off-screen friendship that affected production. Awkwardly, Carrie Fisher, who plays Sally’s best friend Marie, was best friends with Reiner’s recent ex-wife Marshall.
Nobody liked the title
So they have a great script and they’re ready to start filming. Just one question: What are they gonna call it? Ephron’s original title was How They Met. She also tried Boy Meets Girl, Just Friends, Words of Love, and Harry, This Is Sally.
Reiner went so far as to hold title-naming contests while shooting. The prize for picking the winning title? A full case of champagne. Ultimately, they decided on When Harry Met Sally…, with the “dot dot dot” suggesting there’s more to the story than you think.
Ryan and Crystal disagree on the film’s central question
At the end of the day, can men and women be friends without sex getting in the way? Ryan told USA Today: “Yes, men and women can just be friends. I have a lot of platonic (male) friends, and sex doesn’t get in the way.”
Crystal, on the other hand, said: “I’m a little more optimistic than Harry. But I think it is difficult. Men basically act like stray dogs in front of a supermarket. I do have platonic (women) friends, but not best, best, best friends.”
Crystal thought it would flop
The summer of 1989 featured a slate of huge blockbusters, like Batman, Indiana Jones and the Last Crusade, and Ghostbusters II. And also, a tiny romantic comedy about feelings. Needless to say, Crystal was pessimistic. He was sure, given the competition, that the movie wouldn’t make any money.
Lucky for us, Crystal was wrong. The studio, Paramount Pictures, only released it in a few theaters at first, letting excitement and word-of-mouth travel. By the time it was playing across the country, it made $93 million, earning everyone a nice chunk of change.
They filmed that infamous scene at a real restaurant
To shoot Meg Ryan’s, ahem, “fake example,” the production team chose Katz’s Delicatessen, a real, famous deli in New York City. Founded in 1888, it became a popular hangout for WWII veterans. So popular that they invented this silly slogan: “Send a salami to your boy in the army.”
If you ever visit Katz’s Deli for what is objectively the best pastrami sandwich in the world, you’ll see this sign, commemorating the filming of the classic scene: “Where Harry Met Sally: Hope you had what she had.” But, also, we hope you didn’t bother the other customers too badly.
There are now contests for “faking it”
Called the “I’ll Have What She’s Having” contest, enthusiastic participants head to Katz’s Deli to see who can “perform” the best. Five winners are chosen by deli owner Jake Dell, judged on “enthusiasm” and “commitment.” Talk about dinner and a show!
Hashtags for the event include #katzsdeli, #fakeitlikemeg, and #whenharrymetsally. One contestant, 24-year-old teacher Anna Naples, was especially excited: “‘When Harry Met Sally’ is one of my family’s favorite movies… so I couldn’t leave without imitating the scene.” It’s one of our faves too, Anna — and we ain’t faking that.
Everyone agrees it was a risky movie to make
We should consider ourselves lucky that When Harry Met Sally exists, because studios were scared of it. Ephron said “it has no safety net… It entirely depends on your caring about those two people. There’s no real plot. We were so lucky.”
Obviously, Ryan and Crystal used their movie star charms and sold the movie. But Crystal told a crowd at a Turner Classic Movies screening it probably wouldn’t get made today, because no one would take a chance on a movie solely about people talking. We’re glad they did at least once!
You can see Ryan cracking up in one key scene
Remember when Harry starts talking about “pecan pie” in a funny voice at the museum? Crystal was fully improvising, making Ryan break character and laugh. She even looked at Reiner to see if she should keep going — and it was all left in.
The movie had tons of improv and collaboration, even in its most famous scene. Ryan actually suggested she show Harry how to “fake it” in a public place — it was originally just a conversation. And Crystal suggested the immortal line, “I’ll have what she’s having.”
It directly inspired Reiner and Ephron’s next movies
In one scene, we see Harry reading Stephen King’s Misery, a book about an obsessed nurse who kidnaps and tortures her favorite author in one scene. Guess what movie Reiner directed one year later? Misery, starring James Caan and an Oscar-winning Kathy Bates.
In another scene, Harry and Sally meet each other at Shakespeare and Co., a local NYC bookstore. Years later, it was shut down when a Barnes & Noble moved in close by. That inspired Ephron to write and direct the romcom classic You’ve Got Mail, starring Tom Hanks and, obviously, Meg Ryan.
There were some awkward family moments around that famous scene
You may know that Estelle Reiner, mother of director Rob, delivered the famous line, “I’ll have what she’s having.” But did you know that Rob had to make lots of “noises” in front of his mom to guide Ryan’s performance? Yikes!
Years later, Ryan’s fiance, singer John Mellencamp, showed When Harry Met Sally to their 14-year-old daughter. What a fun way to share the family business, right? Wrong. When that scene happened, Mellencamp panicked, yelling to Ryan, “Meeeeeeeeg! I’m not explaining this!” That’s one way to have “the talk”…
You won’t believe how long that four-way phone call took to make
“On the surface, that scene looks like the simplest thing in the world.” That’s Reiner talking about the hilarious four-way phone call between Harry, Sally, Marie, and Jess (Bruno Kirby). So how did a two minute sequence take an entire shooting day to make?
It involved three separate cameras recording three separate sets at once, which is unusual and complicated. One take was ruined by a bird rustling. One take was perfect — until a final line screw-up by Kirby. Finally, after a long 61 takes, they nailed it. And presumably collapsed from exhaustion.
The “faking it” scene confused a lot of men
Ephron went to a Las Vegas test screening, and noticed that when Ryan let ‘er rip in Katz’s Deli, male audience members were stunned silent. “They didn’t get it. The women, however, did. They laughed, and their laughter became infectious until, one by one, the men joined in.”
Ephron wasn’t sure “whether the women had, in effect, given the men permission to laugh, or whether the men were being told that something up on the screen was funny and they had better laugh or look stupid.” In other words, they had what everyone else was having.
Reiner believes the movie changed him as a person
“You know, you don’t have to tell everybody everything that’s going on the moment it’s going on.” A classic line from a movie full of them. It comes directly from a conversation between Ephron and Reiner — one that Reiner took to heart.
Reiner, like Harry, had a tendency to overshare. And Ephron, like Sally, called him out on that. Reiner reflected on this later: “You don’t need to be out there all the time just spewing. It’s how you become an adult, and I think [Ephron] helped me see that.”
Many critics originally disliked the movie
Sure, Harry can be a bit of a killjoy. But he’s got nothing on The New York Times. When they reviewed When Harry Met Sally, they called it “amazingly hollow.” Variety said, “the plot mechanics began to unwind and the film begins to feel shapeless.”
Other critics recognized it for the classic it is. The Los Angeles Times called it “an unqualified delight.” The Washington Post said “it’s a move that walks on air.” And Roger Ebert loved “the chemistry between Crystal and Ryan.” We give two thumbs up to these positive opinions.
Crystal had a wild thought for the opening
Some movie stars might be concerned about looking good onscreen. Not Crystal. He wanted Harry to look bad, right from the opening scene. And as a college-aged Harry and Sally start their long, accidental road trip, Crystal had an idea to really turn the screws.
Eating grapes is normally an inoffensive activity. But in Crystal’s hands, it became an annoying nightmare. He improvised eating grapes loudly, spitting seeds out the window and making Ryan’s annoyed reactions that much more real. And the scene perfectly introduces their iconic dynamic.
One key scene was completely unplanned
Pictionary should be a simple game. One person draws a clue without saying words, everyone else guesses what it is. Yet Pictionary always results in bonkers guesses like “Baby fish mouth” being screamed. And that’s exactly what Reiner wanted for this scene.
Reiner’s exact instructions to his cast? “Do whatever you want to do.” Ryan was given the clue “baby talk,” and that was it. “There was nothing in the script,” Reiner told Entertainment Weekly. “We just asked her, ‘How would you convey ’baby talk’?” Ryan’s castmates… well, they tried their best.
One costar made lots of contributions to the script
Best known as Princess Leia, Carrie Fisher steals the show as Marie, Sally’s tough-as-nails friend. She also secretly helped write the script, without stealing credit. Crystal noticed, though, calling Fisher’s contributions a big reason “why I think it’s such a powerful screenplay.”
Fisher carved out an impressive second career as a writer, including the acclaimed, autobiographical Postcards From the Edge. She also helped rewrite scripts for Hook, The Wedding Singer, and virtually all of the Star Wars films she appeared in.
Did you miss Reiner’s cameo in the film?
At the climactic New Years party, you can hear someone say this classic line: “Hey everybody, 10 seconds until New Year.” Okay, so maybe it’s not as famous as Crystal or Ryan’s speeches in the scene. But it’s a fun, winking cameo from Reiner.
Besides directing, Reiner is also a prolific actor, including a starring role on All In The Family. In one episode, his character Meathead once talked about not understanding Auld Lang Syne. In When Harry Met Sally, Harry talks about this exact same thing. Coincidence? Or a sneaky little reference?
The soundtrack was a surprise for everyone
Against conventional wisdom, Reiner didn’t want modern pop stars on the soundtrack. He wanted something timeless. And when he was given a tape of crooner Harry Connick Jr. doing his jazzy thing, Reiner was awestruck. He thought Connick Jr. sounded just like Frank Sinatra.
Connick Jr. recorded lovely versions of jazz standards for the film’s soundtrack, including “It Had To Be You” and “I Could Write a Book.” The released soundtrack hit number 1 on the Billboard jazz charts and won Connick Jr. a Grammy.
Ryan and Crystal almost played a couple two years earlier
Crystal was in 1987’s dark comedy Throw Momma From the Train, directed by Danny DeVito. Ryan actually auditioned to play Crystal’s girlfriend, and Crystal said, “Well, God, it’s so natural… We weren’t even trying and it was just great.”
However, DeVito went with Manhunter’s Kim Greist for the role. Crystal later wondered what it would be like if Ryan had been cast in Throw Momma From the Train. Would Reiner still have chosen her? Or would he have chosen someone he hadn’t seen play Crystal’s girlfriend before, to keep it fresh? We’ll never know.
It was adapted into a 2004 play
15 years after the film’s premiere, a stage adaptation of When Harry Met Sally opened in London. Harry was played by Beverly Hills, 90210’s Luke Perry. Alyson Hannigan, of How I Met Your Mother fame, played Sally. The production, unfortunately, got mixed reviews.
The Guardian called it “a dull play” and complained it was a pale comparison to the movie. Later in the play’s brief run, Perry was replaced by Lois & Clark’s Michael Landes as Harry. Stepping in for Sally was one of Reiner’s original choices: Molly Ringwald.
A sequel was (very) briefly considered
The fans loved it. The studio made money off it. So why didn’t Crystal, Ryan, Ephron, and Reiner ever get together again for a sequel? It’s simple: none of them had a good idea for one. But, to their credit, they did try.
After some meetings and discussions, Crystal and Ephron kept hitting a roadblock on the same question: “Why? What are you going to do?” Ultimately, it’s probably for the best we only got one movie. As Crystal put it, When Harry Met Sally’s ending makes “you believe in happily ever after.”
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