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Movies of 1998 Bracket Game: You’ve Got Mail Vs. The Wedding Singer

1998 is right in the middle of an era in cinema that I have great affection for. The success of former video store employee Quentin Tarantino had been hugely influential and motivated a general expanded interest in independent film and in the value of both movie trivia and the expertise of your local hole-in-the-wall movie rental clerk. Many of the bigger studios had scrambled to put together projects and promote filmmakers who would help to bolster their street credibility and make them seem in tune with the times. While at moments this resulted in some movies that only had the markers associated with the sort of stuff they thought we wanted to see, but none of the genuine connection with the material that had made it interesting to begin with, I’d say the overall result was positive. Creative and idiosyncratic efforts were more likely to get the green light, and I consider that to be a good thing. At the same time, we were still getting a lot of very mainstream movies with pretty varied results, which served to remind us both of the value of earlier studio approaches and of the corporate malaise that independent films were in part a reaction against. It was a fine time to be a movie fan.

To begin the lower half of our 1998 bracket we’re representing the rom-com cinematic trend with two pretty traditional examples of the genre, but from slightly different generations. I would argue that while a Tom Hanks/Meg Ryan movie is pretty appealing overall, it is most appealing to younger baby boomers and that including Adam Sandler and Drew Barrymore aims your movie more toward younger members of Generation X. I have a mild appreciation for both of these movies, so maybe that says something about where I sit on this spectrum? Let’s take a look at both You’ve Got Mail and The Wedding Singer.

But first, let’s take a look-see at the results of yesterday’s animation smack down. This time we had a relatively close contest, with Disney’s tale of a heroic girl Mulan winning with 56% of the vote. Milan and her dragon Mushu will face off against Deep Impact in the second round.

You’ve Got Mail was the third romantic comedy to pair Tom Hanks and Meg Ryan, with Sleepless In Seattle helping to boost both of their careers five years earlier while LeBlog favorite Joe vs the Volcano mysteriously did nothing for them. The source material for the 1998 rom-com has a pretty rich history of its own, tracing back to a 1937 Hungarian stage play called “Parfumerie.” That story was later adapted for the screen in 1940 by Ernst Lubitsch (Ninotchka, To Be or Not to Be, Heaven Can Wait) into The Shop Around the Corner starring Jimmy Stewart. That film was then adapted into a movie musical starring Judy Garland called The Good Old Summertime in 1949. That all happened relatively quickly, but then fourteen years later the same story was adapted into a completely separate stage musical called She Loves Me (a show I took a small role in once in 1995). Each of these previous versions of the story revolved around a man and woman who knew one another in real life but were unaware that they were secret pen pals. Nora and Delia Ephron saw the opportunity to update this conceit with what was then a relatively new internet culture on which people could meet, but still conceal their identities. This led to one of the bigger criticisms of the movie in charges of product placement due to its characters’ repeated use of the America On Line (AOL) email service with the logo and sound included.

While You’ve Got Mail was a bit of a yuppie fantasy set in the Upper West Side in New York City, the Adam Sandler vehicle The Wedding Singer was decidedly more relatable to most younger audiences, set in middle class suburbs and featuring waitresses and wedding singers (duh). Sandler, like it or not, was one of the biggest movie stars in the United States at the time, and it could easily be argued that his football comedy The Waterboy is more deserving of a place on this bracket. after all, that movie was number five for the year at the box office, while The Wedding Singer was just twenty-fourth, behind such forgotten fare as Everest and Stepmom. It comes down to two things, though. Firstly, The Wedding Singer pairs better with You’ve Got Mail as a romantic comedy, and secondly I just like it a lot more. This way we get to have Adam Sandler represented with a movie that is actually kind of sweet. Of course the trailer below makes sure to include all of the most obnoxious bits in the movie. As a film that is largely based on nostalgia, inclusion of The Wedding Singer is also kind of meta, since this bracket is also very much about nostalgia. For anybody near my own age, the evocation of leg warmers and Culture Club and wine coolers does hit a sort of trashy sweet spot. It also appears to some degree that The Wedding Singer has been better remembered than many of Sandler’s other films, inspiring a hit soundtrack and a stage musical adaptation in 2006.

So which rom-com do you have feelings for? Vote here and confess your crush in the comments section.

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Posted on January 21, 2018, in Bracket Game, Movies and tagged , , , , , . Bookmark the permalink. 9 Comments.

  1. Wow… I hate, hate, hate both of these movies. So badly even that I can’t pick the lesser of two evils – so I’m not going to vote this round. 😂

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    • Really? I was no fan of You’ve Got Mail, but I didn’t hate it. I actually really like The Wedding Singer and I am no fan of Sandler.

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    • I totally understand that this part of the bracket might not be to the taste of a lot of people. Honestly, if I was ranking these movies 1-16 these two would definitely end up in my lower third. My affection for The Wedding Singer is mostly based on ’80s nostalgia and the fact that it’s an Adam Sandler movie that isn’t flatly shallow and unpleasant, but actually kind of sweet and filled with mostly nice people. There is an undeniable corporate sheen to You’ve Got Mail, but there’s also enough real talent on display that it skirts by with a modicum of charm. I’m guessing today’s winner will get its ass handed to it in the second round, but this matchup doe help to accurately represent what movies were like in 1998.

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  2. YOU’VE GOT MAIL is an inferior remake of a great Jimmy Stewart movie. THE WEDDING SINGER was the last good (and one of only two or three that were good) “Adam Sandler” movies. I think you know what I mean by that. TWS gets my vote.

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    • I’m guessing what you mean is that movies like Punch-Drunk Love, Spanglish, and Funny People don’t count as “Adam Sandler” movies because they don’t adhere to the tone and style of humor that are mostly associated with his flicks. I guess I’d probably agree with you, but I’d say that The Wedding Singer is a little outside that range too. Not it the same way, but definitely different enough to make it appealing to me.

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      • I typically use “Adam Sandler movie” as short-hand for Happy Madison Productions starring Adam Sandler. He’s made other (better) movies, but they are off-brand.

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  3. I can’t believe this one is as close as it is. You’ve Got Mail is the weakest pairing of Hanks and Ryan. Watchable, but you’d be better off watching Sleepless in Seattle. Or better still, Joe Vs. the Volcano. Plus, is it possible to be any more dated than an AOL movie?

    The Wedding Singer is a legitimately funny and surprisingly sweet movie that still holds up. Easy vote for me.

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  4. Of course I went for The Wedding Singer. It’s far from my favorite movie. But as far as early Sandler goes, it’s one of the better ones. Billy Madison, while it had a few good moments, never really extended far above toilet humor. Happy Gilmore, which I admit to a certain guilty pleasure enjoyment of, is one of those movies you like but don’t want to admit to liking. And you can’t say anything nice about Bulletproof so don’t say anything at all.

    The Wedding Singer has a story that’s pretty predictable. But it still entertains. The emphasis on 80s kitsch a decade after makes it work as a nostalgia piece and it still holds up even after 80s nostalgia has been replaced by nostalgia for the following decade. And Sandler does broaden his range a tad.

    The interesting thing about You’ve Got Mail is that it’s easily the least and most dated of the Hanks/Ryan romcom trilogy (Joe Vs The Volcano is easily the best), it still has an audience. Not a particularly large one. But there are people I know who are major romcom fans who still like it. This is even now, 16-17 years after AOL itself became more or less irrelevant.

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  5. Although i had much more fun with The Waterboy and Happy Gilmore, i still like The Wedding Singer much more than you’ve got mail. The true story behind the Waterboy is just so sweet and funny (No disrespect to any of the actors). I was even a fan of Sandler at that time even Though i prefer Balk, Bates and Winkler which are much more creative and in your face. Waterboy is still one of my faves 90s spoof film. The Wedding Singer was still almost as brilliant i must admit but they didn’t have the sweetness and ridiculusness of the real life behind it to encourage things to move along.

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