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You’ve Got Mail Vs. Sleepless in Seattle: Fight!

A few months ago, Vulture staffers discovered a terrifying truth about their noble leader: Josh Wolk does not like You've Got Mail. Horrified, staffers begged him to explain this insane position, and they later discovered that he prefers Sleepless in Seattle. Here, on Valentine's Day, Wolk and Margaret Lyons pit Ephron against Ephron in an exploration of the Tom Hanks and Meg Ryan romance staples You've Got Mail and Sleepless in Seattle. Which is better? Which is truer? And do children really like the new Star Wars movies?

Josh: A couple of years ago, when Mindy Kaling declared You’ve Got Mail the ultimate rom-com, I assumed it was just a personal, wrongheaded quirk — like children who prefer the Star Wars prequels over the original trilogy — but then in our staff meeting, a bunch of you began citing the movie yourselves as the ne plus ultra of romantic comedies. When I said it was simply an unsuccessful reunion that existed only to milk residual good feelings to the cast (the Fierce Creatures to Sleepless in Seattle’s A Fish Called Wanda), all women — nearly to a one! — winced and declared that Sleepless in Seattle was actually not very good. And I had an up-is-down-down-is-up reaction that lasts to this day. What kind of madness is this? I distinctly remember attending a media screening of the movie in 1998 (in the very same Lincoln Square theater in which Meg Ryan and Greg Kinnear fight in the movie) and finding it an interminable cutesy-thon (complete with Meg Ryan bippity-boppity-booing around in pajamas like she was starring in a body-switching movie with an Olsen twin) that made no logical sense. When I revealed that I was actually on a bad date for that screening, you and your Mailies accused me of being tainted. But guess what: I watched it and Sleepless again this week, and my case stands. Sleepless in Seattle — while not a timeless classic — still holds up as a frothy, heartwarming delight, while, if I were Gene Shalit (and oh God, why can’t I be?), I would say, “You’ve Got Mail? More like Return to Sender!” (RIP Saturday U.S. Mail service.)

Margaret: First, no children prefer the prequels. It's not possible. Second, I of course consider When Harry Met Sally to be the ultimate, perfect rom-com. (And for it to also be secretly about me: University of Chicago grad who writes for New York Magazine? That is me! I am the only one right now! I order salad like a normal person, though.)

But anyway: You've Got Mail is a vastly superior movie for a number of reasons. First, the romantic leads actually interact with each other for most of the movie. Second, in terms of Meg Ryan cutesiness, I prefer Kathleen's version (YGM) to Annie's version (SIS). Kathleen runs a children's book store! She actually believes in that twinkly light stuff! But Annie has strong opinions about china settings because she is secretly horrible. Finally, I find Sleepless to be a bit creepy, honestly. The big romantic moment at the end involves 8-year-old Jonah proudly telling a taxi driver, "I'm going to meet my new mom!" Yiiiiiiiikes. Also, having a ton in common with someone's deceased partner just seems like a recipe for disaster to me. Why doesn't that bother you more?

Josh: First things first: You are going to have to brace yourself for a harsh wake-up call when you or your friends start having kids and they sit raptly during the Star Wars prequels and find the old ones kinda slow. I feel like you need to start working up a callus to that epiphany now, because it sounds like it is going to be painful.

Anyway, back to the debate at hand. So let me get this straight: You find it creepy that a woman (one engaged to a sniffly milquetoast) would fall in love with a sensitive, lonely widower that she hears on the radio. And yet you do not find it creepy that a guy discovers that the heretofore unseen dream date with whom he has been chatting online is in reality the woman he just gleefully put out of business, and he reacts by promptly starting to act like a dick to her, rubbing in her face the fact that her idealized man has stood her up — all while knowing full well that he himself is the one who has stood her up? That doesn't seem the least bit sadistic to you? Sleepless is unrealistic, sure, but its theory that Annie and Tom Hanks's Sam are destined to be together is meant to be pure fantasy: They never speak, but when they meet, they just know it's right. But You've Got Mail, in its urge to have Kathleen and Tom Hanks's Joe Fox adorably bicker and banter before realizing their true feelings, actually makes Joe a real bastard. Yes, you can theorize that, in the real world, Sleepless's Sam and Kathleen may well likely find after they hang out for a while that they actually have nothing in common. But the very fact that they never meet until the Empire State Building makes that kind of reality check moot: This fairy tale does not take place on any planet Earth I know, so who cares? But You've Got Mail is set in a New York where big-box stores put little stores out of business. So when Joe and Kathleen smooch in the park (a dog hugging them instead of a little boy), it is in a very real world, one in which it is very logical to imagine that, no matter how besotted Kathleen may be, when things get quiet she will find herself thinking, You motherfucker, you drove the store my own mother started into the ground.

Margaret: Haven't you ever chickened out in the face of love? Sure, Joe Fox, F-O-X, starts the movie as a stone-cold corporate jerk, but it's because he's scared — scared of love, scared of intimacy (how many times has his dad been married?), scared of connection. But he wants those things, which is why he has an e-mail buddy in the first place. Kathleen's comfortable with love and intimacy, but she's afraid of standing up for herself, of, in her words, being "brave." Their love helps both of them grow!

Speaking of love and growing, both movies are also about grief. Obviously in SIS that's the main deal for Sam, but Kathleen in YGM is in her own state of mourning over her mother. This line makes me actually cry every time, and I am teary just typing it out: "I feel as if a part of me has died, and my mother has died all over again, and no one can ever make it right." I guess I don't buy that Annie's love will soothe Sam's grief, but I do think that Joe's love soothes Kathleen's.

Is Bill Pullman a worse boyfriend than Greg Kinnear?

Josh: I think you are reading too much into these characters; they are just playing pieces set up to surmount impossible odds and then kiss at the end. Joe Fox isn't built as a man who doesn't know how to love, like some sort of Matthew McConaughey rogue who never stays the night: He is in a relationship with Parker Posey's tightly wound straw-girlfriend. He can love — he just hasn't found the right person, in the same way that Kathleen has a boyfriend in Greg Kinnear's self-centered Observer columnist. (In retrospect, it's funny to remember a time when chain bookstores were the powerhouse, but I do not remember a time when an Observer columnist set the city's agenda. I mean, Candace Bushnell, sure, in a slightly different way ... ) And funny you should mention Greg Kinnear and Bill Pullman: That underscores what I said about how these characters' complicated emotional life is a nonissue. Both of Meg Ryan's boyfriends in these movies exist solely as irritating mannequins there to simply irritate that she needs more from a partner than what she has. In any other movie with a love triangle, the bad boy- or girlfriend doesn't go out without a fight. But in both cases here, when Ryan confesses that it's time to break up, they both shrug and go, "Whaddya gonna do? I wish you the best! High five!" Your cell-phone service provider would put up more of a fight if you broke up with them. And in You've Got Mail, the breakup with Parker Posey happens off-camera; it's just something Joe mentions as he heads off to live on his boat. So don't give me any of that "This is what Joe Fox really feels!" Neither movie really gives a damn what Hanks's or Ryan's characters really feel, but at least in SIS it's beside the point.

By the way, to go back to the aforementioned McConaughey, Joe Fox would have made more sense as a character if double-M were playing the role. It makes the movie feel all the more nonsensical that Joe smacks his lips over the prospect of decimating the tiny, landmark kiddie bookstore, but is a sweet guy in every other way, the kind who likes to ride in a tiny merry-go-round like he's back in Big. It makes his snickering with the Fox dad and granddad over their path of destruction really weird, and Joe and Kathleen's mean repartee inexplicable. Yes, titans of business have many colors and are not necessarily demonic killers (and Nora Ephron seems to try to be getting across this "nuance" when her camera lovingly pans over the kids reading in the aisles at Fox Books), but this romantic comedy is telling an inherently simplistic parable: When you strip life's complications away, true love will win out! So a good-hearted rapacious executive makes no sense. This movie would have made more sense if Matthew McConaughey ran the place and didn't even know how to read, or walked around burning Dr. Seuss books and replacing them with a series starring the Taco Bell chihuahua.

Margaret: I feel we have reached an impasse. That's largely because your heart is made of stone — because you don't actually like either of these movies — but also because you think it's possible to read too much into You've Got Mail. This movie stands up to Talmudic dissection, Josh. When I get my PhD in Ephronology, my thesis will be called "Slouchy Pants, Thick Belts, and the Knee-Length Skirt: Gendered Millennial Fashion and Kathleen Kelly's Sense of Belonging." I will TA a course in supporting casts called The Violin, The Violin: Social Affiliations and the Facets of Personhood, which will explore how the secondary characters in YGM and SIS each represent particular aspects of our main characters. You are also welcome to participate in the lecture series Call Me: Tracing the Differences Between Face-to-Face and Mediated Communication in the Nora Ephron Canon. Our rivals at the Nancy Meyers Institute of Cashmere Wraps are very jealous of all of this, of course.

In the spirit of love and heartstrings, though, can you do one thing? Can you name anything you like about YGM?

Josh: First, I must protest: I like SIS. Rom-coms aren’t my go-to genre, but I am not made of stone, nor petrified wood, nor stale candy hearts! You ask for one thing I like about it? I concede that I got that reflexive ga-gung in my gut at the end when Kathleen looks tearfully at Joe and says, “I wanted it to be you. I wanted it to be you so badly.”

Unfortunately, it took what felt like six days of perkiness and faux hatred scored to literal-lyric-ed soul and jazz standards to get there. (The only reason there wasn’t a song in the movie called “You Just Finished the Chapter in the Closed Bookstore of My Heart” is because Stevie Wonder never got around to writing it.) I can get the same choked-up reaction that YGM took two hours to build to by just going to YouTube and spending two and a half minutes watching Kevin’s game-winning catch in the movie Parenthood. Yep, just watched it, and it happened again. And Steve Martin’s jeans were anything but slouchy.

Help us settle it once and for all, readers. What is the superior film: You've Got Mail or Sleepless in Seattle?