Sleepless In Seattle Vs You've Got Mail

Round 1: Plot

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These two romantic comedies both star Tom Hanks and Meg Ryan and were released five years apart. Their stories are very different, however, so the first thing we’re going to delve into is plot. First, let’s look at “Sleepless in Seattle,” released in 1993. Sam Baldwin, played by Hanks, has recently become a widower, and moves across the country with his son, Jonah, to live in a houseboat in Seattle. One day, Jonah calls into a talk radio station telling his family’s story, and soon enough there is an onslaught of women trying to gain Sam’s attention. Annie (Meg Ryan), is one of the women who heard the radio segment and becomes enamored with Sam from afar. It all ends, of course, with a rendez vous at the top of the Empire State Building, and a romantic classic is born. “You've Got Mail” is a much more modern feeling movie (well for the ‘90s at least), namely because it has email at its core. Kathleen and Joe meet in an only chatroom for “over 30s” and hit it off, starting to email one another frequently. Kathleen runs an adorable small bookstore in New York, and unbeknownst to her, Joe is about to open a big-name book store in her neighborhood which threatens to ruin her business. While the two meet in real life, they don’t realize that they’re interacting with the people that they developed online crushes for. While the plots of both these movies have a lot of merits, we have to give this first round to “Sleepless in Seattle” because it has the vibe of a classic romance, and still feels more timeless to rewatch even decades after its initial release.

Round 2: Meg Ryan's Character

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Now that we’ve covered the plots of these two films, let's do a deep dive into the characters. In “Sleepless in Seattle,” Meg Ryan plays Annie Reed, a woman who works as a journalist writing for the Baltimore Sun. She’s planning to marry a man named Walter, but she knows deep down that their relationship isn’t quite right. She becomes consumed with the idea of Sam after hearing him and Jonah on the radio and, inspired by the film “An Affair to Remember,” she writes to him asking him to meet her atop the Empire State Building on Valentine’s Day. She then goes to Seattle and observes him, and the two finally meet, though fleetingly. While this could be read as romantic, it could also be seen as kind of creepy, which is why we’re docking some points here. In “You've Got Mail,” Ryan’s character Kathleen Kelly is about as charming as they come. She has inherited The Shop Around The Corner on the Upper West Side from her mother, and works as an independent bookseller in a world where big box stores seem to be taking over (this was before Amazon destroyed them all of course). Like Annie before her, Kathleen is also in a relationship when the story begins, and it’s just as clear that it isn’t meant to be. Kathleen is sweet, optimistic, and absolutely the hero of this story. While they each have their quirks, we’ve got to give this point to Kathleen, just because she never gives off any weird stalker vibes.

Round 3: Tom Hanks' Character In “Sleepless,” Sam Baldwin pretty much instantly gains our sympathy because he has recently lost his wife to cancer and becomes a single dad to a pretty adorable and precious son. Sam has an instant likeability, because he’s sensitive and clearly has the capacity to love, which of course makes women swoon. He’s understandably skeptical about the idea of meeting a woman who is essentially a total stranger, which makes us realize that he’s actually a realist and doesn’t have his head in the clouds. He’s basically the type of guy any one of us would like to meet. Joe Fox, on the other hand, is kind of a jerk. Joe is part of the Fox family, which runs a major chain of bookstores called Fox Books. He’s about to open up the latest branch just around the corner from Kathleen’s store, and goes in and meets her without revealing the fact that he has a bit of an ulterior motive. When she finds out and is upset with him, he disparages her store, and basically treats her terribly. He clearly has a corporate mindset and doesn’t really care about stomping all over the little guy. When he finds out that Kathleen is the woman he has been talking to on the internet, he basically makes her think she has been stood up. For the whole end section of the movie, he continues to manipulate the situation without revealing who he is. Meg Ryan’s “You've Got Mail” character may have won the last round, but Sam from “Sleepless in Seattle” is the clear winner here. We wonder what would have happened if Sam and Kathleen had met? WINNER: “Sleepless in Seattle” 2 / “You've Got Mail” 1 Round 4: Realism Like many of the great love stories, “Sleepless in Seattle” is based on pure fantasy. A man appears on a radio show, still grieving his wife, a woman happens to hear and has a feeling that this could be something real. When Sam sees Annie for the first time, he experiences something like love at first sight, and in the end these two basically commit to one another without actually knowing each other at all. Is it realistic? Absolutely not. But does it matter in the context of the story? Nah, not really. While “Sleepless” may intentionally have the magical elements of a fairy tale, “You've Got Mail” is a distinctly modern story that is clearly set in a very real world where independent bookstores close, and people meet online rather than in romantic chance encounters. Now is it believable that these two characters are able to spend so much time together without Kathleen realizing that Joe is actually "NY152"? Maybe not. Both of these movies have some elements that make them a little bit hard to believe, but in the end, we feel that “You've Got Mail” is a story that is much more rooted in reality. WINNER: “Sleepless in Seattle” 2 / “You've Got Mail” 2 Round 5: Romance In terms of romance, “Sleepless in Seattle” has it in spades. What’s more romantic than the idea of two strangers just knowing that they’re right for each other against all odds, when they’ve barely even met? Though it’s a riff on another older film, meeting at the top of the Empire State Building is a classic romantic move, and while watching this scene we were desperate for the two characters to actually cross paths. While it may not be a story that has its feet on the ground, we can’t help but fall in love as much as Sam and Annie do. In “You've Got Mail,” we get to see a more modern version of romance. Though we may not be using AOL to communicate anymore, more and more people are meeting on dating sites or even apps, so this movie is romantic in a more relatable way. The thing is, though, this movie doesn’t actually feature a whole lot of romance. The two leads antagonize one another for much of the story. Only at the very end do these two actually interact with one another (while actually knowing who the other is), so there aren’t a whole lot of grand gestures or impassioned speeches. This one’s pretty easy, it has to go to “Sleepless in Seattle”. WINNER: “Sleepless in Seattle” 3 / “You've Got Mail” 2 That means “Sleepless in Seattle” takes this one! Which movie do you like more? Be sure to debate it in the comments and of course, don’t forget to subscribe to MsMojo for more divisive versus battles.