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The Great Gatsby was a critique of the 1920s that had the misfortune of being published in the 1920s and so was hated by people who thought the 1920s were just great. It was then rediscovered by the generation that had grown up in the great depression that followed the stock market crash that ended the 1920s and was in the middle of fighting a world war against fascists who had gotten their start in the 1920s while all the non-fascist adults had been too busy drinking and having fun to do anything about it. So it is loved more for its prescience and pointing of flaws that would become more obvious to those who had grown up in the rubble left by its collapse than for actually being a good book in its own right. No doubt the idea of having to live through the consequences of their parents' generation ignoring a market bubble leading to a massive economic collapse and rise of totalitarianism is something very difficult for modern audiences to relate to.
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