An Official Ranking of Nora Ephron’s Meg Ryan Trilogy

Hello, everyone! Let’s take a cozy stroll through the pristine streets of New York City, a place where gaily decorated children’s bookstores glow under the warmth of yellow streetlights, lovers frolic beneath clean white snowflakes, and a journalist can easily afford to live in a brownstone on the Upper West Side. I’m talking of course about Nora Ephron’s New York City, a location that exists only in the movies, but is still enchanting enough to beguile us into believing that dreams do come true. At least, if you’re Meg Ryan.

So today, I want to present my totally official and not-at-all biased ranking of Nora Ephron’s Meg Ryan trilogy, which includes When Harry Met Sally, You’ve Got Mail, and Sleepless in Seattle. Not all three movies in the Ryanology are created equal; I might ruffle a few feathers. If you agree or disagree, let me know!

The Best: When Harry Met Sally

Synopsis: Over a twelve year period, casual acquaintances Harry Burns and Sally Albright strike up an intense friendship, but when romantic feelings start to develop, their relationship heads into uncharted territory.

My thoughts: Ephron’s movies are known for their witty dialogue, but When Harry and Sally reigns supreme because the sparkling chemistry between leads Meg Ryan and Billy Crystal elevates Ephron’s dialogue to new heights. Although the plot is structured similarly to a traditional “enemies to lovers” romance, it takes an unconventional turn by focusing on the deep friendship between Harry and Sally, rather than focusing on their sexual chemistry. Their friendship, built on trust, shared beliefs, and most importantly, a profound sense of mutual respect, still remains one of the more realistic platonic relationships shown onscreen to date.

Harry and Sally both embody characters that would become Ephron’s signatures in her later romantic comedies; Harry is a cynical, self-deprecatory smart-ass who secretly longs for love, while Sally is a uptight Pollyanna type who yearns to find someone who understands and respects her. Even though they initially drive each other up a wall, both characters come to respect and value each other’s opinions. They enrich each other’s lives and support each other’s endeavors, and neither party needs to sacrifice their goals or desires to love the other.

The movie questions the possibility of heterosexual friendship. Can men and women be friends without sex getting in the way? Even though the movie ends predictably with Harry and Sally falling in love and getting married, the movie never says that men and women can’t be friends. Instead, the movie proposes the idea that romantic love and platonic love are two sides of the same coin. In the movie, Harry and Sally’s platonic relationship is shown to be as deeply loving as that of the happiest married couple, and yet the only element that separates their platonic relationship from a romantic relationship is sex. Rather than holding up sexual compatibility and physical chemistry as the epitome of romantic love, the movie emphasizes that strong relationships are built on trust, respect, and kindness. And even though such thoughts might now be thought of as too cheesy, the sincerity of Ephron’s script is what makes it work.

The Okay: Sleepless In Seattle

Synopsis: After Sam Baldwin loses his wife to cancer, he and his son Jonah relocate from Chicago to Seattle, where Sam continues to grieve for his dead wife. Determined to help his father find love, Jonah calls into a radio show and convinces Sam to reminisce about his dead wife. Across the country, the newly engaged Annie hears Sam’s story and becomes enamored with him. She writes a letter to Sam never intending to mail it, but her friend secretly takes the letter and mails it to Seattle anyway. When Jonah reads the letter, he becomes convinced that Annie is the one for Sam, and tries to bring Sam and Annie together.

If When Harry Met Sally is about true love blossoming from a deep emotional connection, then Sleepless in Seattle is the exact opposite. It’s a movie about the fantasy of love, rather than the practical realities of a relationship. Again we have a cynical, once-bitten twice shy man played against a hopelessly romantic woman, but while it works like a charm in the first movie, it doesn’t work as well as in the second movie. There’s never a chance for Tom Hanks and Meg Ryan to develop any chemistry, because they only share screen time for a total of two minutes. While the audience gets a sense of their personalities, and Ephron’s script is as witty and heartfelt as before, the story itself is too far removed from the romance to inspire any deep emotion. Unless you believe in love at first sight, the ending where Sam and Annie meet for the first time on the Empire State Building and immediately fall in love rings hollow. Why should we believe that these two will love each other, when the only thing that brings them together is initial physical attraction?

By paying homage to classic romances like An Affair to Remember, the movie tries to present their romance as grand and sweeping, but it can’t come close. The movie is too modern, with too much sprinkled snark, and too little emotional connection, for this fairytale romance to work. Tom Hanks can’t pull of the tender cynicism in the same way that Billy Crystal could; he just seems irritable. And that would be okay, except that the movie depends on the viewer believing that Sam could be just as much of a hopeless romantic as Annie, when every part of his characterization demonstrates the opposite. This isn’t to say that Sleepless In Seattle isn’t an enjoyable movie, because it is. The script is cute and funny, the soundtrack is great, and Meg Ryan perfectly encapsulates the frenetic energy of a feminist 90s woman who still believes in true love. The only flaw in the movie is the romance itself; it’s too fantastical to be believable, and this crucial flaw brings the whole movie down a notch.

The Worst: You’ve Got Mail

Synopsis: When Kathleen Kelly, also known as “Shopgirl,” strikes up an online friendship with a likeminded stranger who goes by the name “NY152”, she has no idea that her internet penpal is her new business rival. Heir to the Fox Books empire, Joe Fox relishes putting shops like Kathleen’s family-owned bookstore out of business, and when the two meet at a party, they quickly become enemies. When Kathleen and Joe agree to finally take their online friendship into the real world, Joe realizes that Shopgirl and Kathleen are one and the same, and stands her up. Now knowing her true identity, he continues their online conversations, and starts to develop real feelings for Kathleen, while Kathleen, reeling from the loss of her bookstore, remains in the dark.

My thoughts: I might be in the minority with my opinion, but I’ve watched this movie twice, and I really dislike it. It’s the same “enemies to lovers” story as When Harry Met Sally, but while the former movie shows a relationship built on trust and shared values, the latter movie revolves around deception, resentment, and the destruction of one person’s livelihood. Once again, Hanks plays a cynical man who doesn’t believe in romance, but in this go-around, he has none of the endearing traits of his character in Sleepless in Seattle, and none of the tenderness and empathy of Billy Crystal’s character in When Harry Met Sally. Hanks’ character Joe is shamelessly condescending and mean, and has no qualms about deceiving a woman he supposedly cares about in order to convince her into loving him. Although the second part of the movie is built around Joe “redeeming” himself through his friendship with Kathleen, the fact remains that his online deception is incredibly creepy. Rather than reveal himself to be NY152 and build an honest friendship, he uses his online conversations with Kathleen against her, always knowing more than she has chosen to tell him, and always keeping the upper hand in their relationship. Poor Kathleen has no idea that she’s baring her soul to a man she hates, and even if her feelings slowly change, it doesn’t excuse Joe’s continued deception.

Kathleen really gets the short end of the stick in this movie. She loses her beloved bookshop and she has to fall in love with Tom Hanks at his smarmiest. The ending scene where Kathleen rejoices at discovering Joe Fox’s true identity is incredibly unrealistic and left a bad taste in my mouth. Joe deceives Kathleen for half the movie and never faces any consequences, while Kathleen loses her livelihood and her faith in the world. If it wasn’t billed as a romantic comedy, I would think You’ve Got Mail is a dark parody of the worst tropes in romance. Kathleen loses everything she’s cherished to a soulless corporation, and her reward is settling for a smug asshole. That’s romance? I don’t buy it, and I would like a cultural re-contextualization of this movie because it doesn’t deserve its reputation as a “heartwarming” romcom.

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