by Jake Hjort, Contributing Writer

Welcome back, fellow time travelers, to another edition of 20th Century Flicks! This month, in a continued effort to check classic cinema off of my list of shame, I’m diving back to the year 1989 to watch Rob Reiner’s When Harry Met Sally... As I carry on with my journey to cover some of Hollywood’s greatest directors of the 20th century, I figured my quest would not be complete without a look-in on Reiner, whose run of films in the ‘80s and ‘90s is among the best of all time. Having long heard that When Harry Met Sally… is one of the best romantic comedies of all time, it seemed a perfect film to put on this month for Valentine’s day and a heartwarming trip to the past. 

Set over the course of 12 years, the film tells the story of Harry Burns (Billy Crystal) and Sally Albright (Meg Ryan), two young adults who meet carpooling from Chicago to New York City. After a contentious car ride with conversations highlighting their differing views on relationships, and whether or not men and women can be “just friends,” the two part ways, never intending to see one another again. However, over the years Harry and Sally continue running into each other around the city, developing a friendship and eventually a mutual romantic attraction. Though there is some continued conflict along the way, the two finally are able to confess their feelings and get married. 

Like any romcom, When Harry Met Sally… can only be as good as the chemistry between its two leads. With this particular pairing, however, there is a unique challenge: There isn’t supposed to be any chemistry at the beginning of the film. Harry and Sally don’t exactly have a typical meet-cute; instead, they don’t particularly like each other at all when they are first introduced. To run the full gamut of connective emotions from disdain to love is no simple task, but Crystal and Ryan do a remarkable job selling every part of the relationship (with some assistance from Reiner’s direction and Nora Ephron’s script). I truly believe that they hate each other at the beginning of the film, that they’re having a lot of trouble processing their feelings in the middle, and that they are in love at the end. 

Of course, the most well-known bit of their relationship — and without a doubt the film’s biggest cultural footprint — is the lunch that Harry and Sally share at Katz’s Delicatessen. In an attempt to prove a point to Harry about his skills of observation, Sally imitates intense feelings of pleasure in the middle of the deli, prompting another patron to famously tell her server, “I’ll have what she’s having.” This scene has been parodied so many times, including as recently as a few weeks ago in a Super Bowl commercial for Hellmann’s Mayonnaise, that I knew it was going to be coming, but I have to say that I was still really surprised by how well it works, not only as a standalone scene, but in the context of the film. It isn’t just a bit that’s played for shock or laughs (although it certainly earns both) — it actually fits well into the progression of both Harry and Sally’s characters.

My favorite bits of the film, however, have almost nothing to do with Harry or Sally. They’re the little vignettes interspersed throughout, which featured short interviews with other couples telling the story of how they met and fell in love. These fragments are heartwarming and funny, and really help to keep the romance alive during the first half of the film when we aren’t getting much of it during the actual plot. The relationship between Harry and Sally ends up being one that you want to root for, but I do think that these little scenes that keep the heart engaged help to prime you to be charmed by Harry and entranced by Sally. 

Of course, this calls into question the film’s main dilemma: Can men and women ever just be friends? Well, if you take the ending of the film as the answer, then I suppose they cannot, as Harry and Sally are not able to remain friends without feelings of attraction complicating things and falling in love. This is all well and good for a movie — heck, it probably would have been pretty disappointing if they decided to stay friends at the end of the film after you got invested in their relationship — but I don’t think that this is necessarily congruent with reality, and I’m a little disappointed that the film is so clear in it’s answer. Men and women certainly can be friends, and though I don’t want to judge the morals of a 35-year-old movie too harshly, this notion that they can’t promotes a culture of gender segregation, and men who refuse to be alone with women. 

I’d be remiss not to point out that this isn’t the first pairing of Ryan and Ephron that I’ve covered on 20th Century Flicks, as I wrote about Sleepless in Seattle last year. Of course, this begs the question: How do the two compare? I have to say, on a structural and story level, I definitely prefer When Harry Met Sally… The relationship between the leads is much better developed (they meet during the first scene, rather than the last) and the romance is much more genuine as a result. However, I do have to say that I was not quite as charmed by Crystal as I was by Tom Hanks. I think that Crystal is still doing a great job, and Harry needs to be a bit rougher around the edges, but I’m just in love with Hanks in a way that I never quite have before with a romcom protagonist, and Harry isn’t able to replicate that. 

When Harry Met Sally… is a great film with two incredibly charismatic lead performances, and it certainly deserves its legacy as one of the greatest romantic comedies ever made. Crystal and Ryan are a great on-screen couple, and Reiner and Ephron make for an amazing creative team; I really think it’s a shame that the two haven’t collaborated again since then. 

You can read more from Jake Hjort, and follow him on Instagram and Letterboxd

Agree? Disagree? Leave a comment now!