Analyze how The Great Gatsby challenges the established values of its time.

The main way in which F. Scott Fitzgerald challenges the established values of his time is by glorifying criminality and tacitly accepting the illegal underpinnings of American society during Prohibition.

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The primary way in which F. Scott Fitzgerald challenges established values is by making a criminal the hero. Although it is never fully explained how Jay Gatsby has made his fortune, adequate information is presented that he has mostly done so by illegal means, especially involving alcohol sales. Closely related to this glorification of individual criminality is Fitzgerald's tacit acceptance of the illegal underpinnings of American society during Prohibition. While some characters claim ignorance of the source of Gatsby's money and criticize or even ridicule him, they take full advantage of his hospitality. Everyone seems to drink a lot. The handful of characters who represent old money do not support conservative moral values. This is most evident in both Tom and Daisy Buchanan, who both have extramarital affairs.

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In many ways, The Great Gatsby is a quintessential example of life in the 1920s, the era in which the novel is set, but Jay Gatsby, one of the main characters, challenges the values of the era with his approach to wealth.

Gatsby shares his wealth by throwing extravagant parties and welcoming everyone. He makes everyone feel as if he is fond of them and wants them around. Gatsby wants to be liked more than he wants to be rich but has no problem using his wealth to make people like him. Later in the novel, we see that he is willing to go to extremes to be loved as well.

Compare this to the stiff, reserved representations of "old money" in the novel, like Tom and Daisy. They aren't nearly as welcoming to Nick as Gatsby is, even though they've known Nick longer. While they invite Nick to their home, they aren't nearly as hospitable or welcoming as Gatsby is. Tom and Daisy are used to the idea of being wealthy, and while they know their money can be used to their benefit, they're reserved in regard to their lifestyle and privacy, keeping secrets of their marriage from even those close to them.

Gatsby, on the other hand, makes a show of his wealth by throwing parties and treating his friends to outings. While Gatsby keeps secrets, he does so to make himself more amiable, and he feels that he has more to lose if his friends stop liking him. Essentially, The Great Gatsby challenges the 1920s values of conservatism and wealth.

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