This question is essential to F. Scott Fitzgerald's The Great Gatsby, as one of the novel's overarching preoccupations is a critique of the American Dream. Consider, for instance, Gatsby and Daisy's storyline: Gatsby begins as a poor young man in love with a young woman (Daisy) who chooses to marry a man (Tom) with vast riches at his disposal. Gatsby believes that, if he just works hard enough, he can earn enough money to become an important person worthy of Daisy's love. In the end, after wasting his life acquiring a vast, but ultimately meaningless, store of wealth and possessions, Gatsby fails to win Daisy's love and dies alone.
It's possible to read this storyline as a critique of the American Dream. In general, the classic American Dream asserts that anyone can acquire all that his or her heart desires, as long as he or she works hard enough. Gatsby's story suggests that this ideal is not realistic. Though Gatsby works hard and claws his way out of poverty, he is not happy in the end, and he fails to gain that which he most desires (Daisy's affection). As such, Fitzgerald is clearly questioning a fundamental American value that informs much of the country's cultural trends, and his ultimate evaluation seems to end in the pessimistic rejection of the American Dream.
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