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By receiving the most votes in the category "Best Picture" I suppose.
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How did this win Best Picture over SAVING PRIVATE RYAN? I think SIL is one of the worst Best Picture winners ever. Yes, a nutty win for best film, the other one for me was The Artist, and if you are like most people your thought is; what is that? My understanding is that Harvey Weinstein was a skilled political wheeler dealer at campaigning and recruiting votes for his films, and in this case it clearly worked. These days Mr Weinstein has bigger problems. I've not seen Shakespeare in Love yet, but I actually liked The Artist (the Vertigo quotation didn't bother me) and have no qualms with it winning Best Picture. However, I will say the rest of your post is pretty spot on
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I'd say the best nominated movie of that year was THE THIN RED LINE, but I like all the others. SAVING PRIVATE RYAN (which I incidentally watched just a few weeks ago for the second time and can confirm is just one really, really good movie) is more gripping and profound than SHAKESPEARE IN LOVE, sure, but the latter is nevertheless a well done and charming comedy with excellent timing and just all in good fun. I sure laughed a lot more watching SHAKESPEARE IN LOVE than I did watching SAVING PRIVATE RYAN. ;-) What is "better" may just depend on the type of movie you are in the mood for. It's silly to compare one to the other and say it is "better" anyway, but that's the way show biz goes. All these movies were good.
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