80s Movie Challenge Week 36: When Harry Met Sally… (1989)

Welcome back friends, for another #80sMC adventure. This week Paul Childs investigates whether men and women truly can be friends without hanky panky getting in the way (Er… I think you might be disappointed with this one boss, PC) with one of the most recent films on our list – 1989’s When Harry Met Sally…

Spoilers follow…


In the last instalment, I talked a bit about how these films we’ve been following week-on-week are eminently quotable. This week’s film is no exception, although it also contains one of the 80s – nay all of cinema’s – great comic scenes. Yes, I’m going to get the elephant in the room out of the way quickly. I’m a polite chap and being British, talking about, er, the art of romance (I thought you said you were going to get to it quickly, Ed) – OK sex – talking about sex in public is not something I’m usually comfortable with. So – let’s quickly discuss the famous orgasm scene and move on (Please do, Ed).

Even the lovely Meg Ryan has a sex face, it appears!

The idea is this; Harry (Billy Crystal) believes that he has always “satisfied” every woman he’s ever been with. Sally disagree and tells him that all women have faked it at one time or another. Harry disagrees and says he would know. So Sally, in the middle of a busy Manhattan diner, decides to prove that fake ones can be as realistic as actual ones.

Ensue much uncomfortable hilarity followed by one of cinema’s great punchlines. But it almost didn’t happen that way at all. When Harry Met Sally… is very much a film about talking. It’s packed with punchy dialogue. Talking things over is a major plot point. And in keeping with that very wordy theme, this scene was intended to be just a witty discussion over lunch. However, Meg Ryan volunteered to act it out rather than just talk about it. A decision she would soon come to regret as director Rob Reiner shot multiple takes. She also didn’t realise before volunteering that it would be acted out in a crowded cafe – an experience she found quite daunting.

Her co-star Billy Crystal also suffered for his art. Ryan just had to perform the fake orgasm, followed by immediately chomping on a forkful of coleslaw. Crystal, however, eats his lunch during Sally’s performance. He went through almost thirty pastrami sandwiches which he later said in an interview was a lot for any Jew.

The “I’ll have what she’s having” line was delivered by Reiner’s mother, Estelle, and that dialogue was also a last-minute insertion, suggested by Crystal. What could have been a fairly dully scene became, completely by accident, one of the great romantic comedy moments. Katz’s Deli in Manhattan’s Lower East Side, where the scene was shot, still pays homage to the film by having a sign pointing out the table where it happened. The cafe is still, over thirty years on, visited by diners intent on acting their favourite scene out – and Katz’s welcomes it with open arms.

OK, that’s the saucy bit out of the way.

Many of these films I’ve looked back at, such as The Terminator, Aliens or The Blues Brothers hold special meaning for me as there’s a fun story surrounding the first time I saw it. I don’t really have such an emotional connection with this film. I didn’t see it when it came out – fourteen year old me was far more interested in Arnie and Police Academy films at the time. I wouldn’t see it for about another five years when I started dating someone who absolutely loved it. She had it on VHS nad invited me round to hers to watch it one time in a double bill with another of her favourite films, Pretty In Pink.

I liked it well enough but didn’t think it was amazing. The girl however, I liked far more. We’ve just celebrated our twenty fifth wedding anniversary a week ago (yes, I was but a mere child when I got married. However, watching it again last night – which is maybe only the second, perhaps third, time I’ve seen it, I began to notice what makes it rather special.

First off, it’s not like other 80s romcoms. Its very subtle. If it wasn’t for one or two fashion and haircut choices, you’d never know this was made so long ago. As it’s set over a long stretch of time (from the mid-70s to an unspecified date at the end of the film – probably early-to-mid 90s) the film kind of works as a period piece. Rob Reiner’s direction and probably more importantly, Nora Ephrom’s script, have a timelessness to them. When Harry Met Sally… feel like it could have been made any time from the late 90s onwards. It really does have a contemporary air about it which many other romcoms have failed to hold on to as they have aged.

Maybe that’s because the crux of the film is centred around timeless issues – friendship and love. The film was written by Nora Ephrom after she met and befriended Rob Reiner. He really wanted to work with her and pitched several romcom ideas to her, which led to lots of discussion of the differences between how men and women approach love and sex. These conversations led to a close friendship between the two and although none of Reiner’s ideas made it to the screen, Ephrom fashioned their actual discussions into the barebones of a story and built the situations and characters around that idea. The two didn’t end up together though, like our titular heroes. No – Reiner’s cinematographer introduced him to a photographer friend, Michele Singer. The couple married in 1989 and Reiner still says that falling in love while filming When Harry Met Sally… actually improved the film as it informed many of his directorial decisions.

While researching different approaches to romantic love, Reiner interviewed several married couples to ask them about how they met, fell in love, and why they are still together. These interviews were transcribed and performed for the camera by actors as the movie’s interludes which break up the various shifts in the timeline.

Although she’d made a name for herself as the love interest or a secondary character in films like Top Gun, Innerspace, DOA and The Presidio, this film was Meg Ryan’s first starring role and it paved the way for her to become one of the biggest stars of the 1990s. It also , in a roundabout way, gave Julia Roberts her similar stratospheric rise to fame. Ryan was approached to play the role of Shelby in Steel Magnolias but after weighing the two films up, she decided When Harry Met Sally… would server her better. This led to the then unknown Roberts securing the role, soon followed by Pretty Woman.


Although he had been Rob Reiner’s close friend for over ten years, Billy Crystal was not the first choice for Harry. Albert Brooks was offered the part but turned it down. Michael Keaton was offered it next but had to decline due to his commitments with Batman. Most interesting of all though, is the fact that Tom Hanks was also offered the role. He also turned it down but would go on to work with Ryan throughout the 90s, with the pair becoming a favourite onscreen couple in films like Joe vs The Volcano and two further Ephrom collaborations, Sleepless In Seattle and her remake of 1940’s The Shop Around The Corner – You’ve Got Mail. She was inspired to make that film while watching shooting on the scene where Harry and Sally meet again after years apart in a New York bookshop.

But this is not just a film about its stars. Bruno Kirby and Carrie Fisher steal every scene in which they appear as the titular couple’s respective best friends. One of the most memorable moment in the film – the scene in which the play Pictionary – was improved by the actors. He told his cast to just play the game as if they were playing in real life. Ryan was given the clue of “Baby Talk” and really was trying to get her co-stars to answer it correctly. All the guesses are real guesses by the actors and Bruno Kirby’s sudden suggestion of “Baby Fish Mouth” was exactly the kind of madcap answer Reiner had hoped to capture on film.

Of their terrible attempts to play the game Reiner said “Well, they tried their best.”

It would be remiss of me to end without mentioning the music of When Harry Met Sally… I mentioned way back in week 2 that Dirty Dancing is credited with a surge in interest in 60s music amongst Gen-X kids and WHMS (yeah, I’ve got fed up of typing the whole title) did the same for swing and jazz music – Harry Connick Jr in particular. Connick Jr was making a name for himself as a pianist at the time and had just released his first album as a singer, 20, when shooting began on WHMS. With his star rising, Reiner asked him to record a number of jazz standards for the film’s soundtrack. Although they sit alongside songs by Frank Sinatra, Louis Armstrong, Bing Crosby and Ella Fitzgerald among others, the album was comprised entirely of Connick Jr’s recordings. It was a huge success, going double platinum and bagging a Best Jazz Male Performance Grammy for Connick Jr.

Crystal was said to be particularly worried about the film’s performance, worrying that nobody would go to see a film solely about two people talking when given the opportunity to see the year’s big summer blockbusters like Indiana Jones and the Last Crusade, Ghostbusters II and Batman. However, it performed far above expectations, taking almost $100m from its initial budget of $16m.

Not bad for a little romantic comedy with hardly any story.


Hey you guys! Don’t forget to join us next week for another fun filled 80s Movie Challenge as we accompany Jane Roberts on a hunt for treasure. Spoiler – she finds it! It’s 1985’s fantastical family adventure, The Goonies!

Paul Childs

As well as writing for Den of Geek and Your Truth, Paul also runs Badgers Crossing, a site for ghost stories. He loves the 1980s and thanks to a keen interest in Public Information Films he has never been electrocuted or set himself on fire.

Join the fun - leave a comment below!