I reread this one immediately after seeing the list, because I couldn't believe it was #2, a classic American novel sure, but number 2?
It is undeniably well written, but the story still leaves me unmoved. Jay Gatsby's pursuit of Daisy Buchanan (& the wealth with which to win her) is apparently supposed to represent the more general striving for the American Dream and his fall would then be a cautionary lesson to those who would pursue the dream.
But the underlying assumption is that the American Dream consists of nothing more than gaining great wealth. Perhaps in the first blush of Marxist Socialism it was possible to so misread man's motivation as being merely materialistic. However, as the Socialist Century ends, we've surely seen that man is motivated by a dream of Freedom, not a lust for wealth.
Thus, the real tragedy of Gatsby is not that he is destroyed pursuing
the American Dream, rather it is that he pursues an empty dream.
(Reviewed:)
Grade: (B)

