#5 The Great Gatsby, F. Scott Fitzgerald

The Great Gatsby is always an American crowd-pleaser, right up until we realize it’s actually a metaphor for all the things that are wrong with us. For F. Scott Fitzgerald, the American Dream had a lot to answer for—and in no way was it self-evident that all men are created equal. Gatsby is a story about how dreams die, and how love dies, and how people die, and how—for the most part—nobody cares.

There’s this whole element of symbolism between the West and the East, but really everyone is pretty much the same: shallow, self-involved, and rich as a cheesecake. The tension between the social classes drives the story, just as it drove the Roaring Twenties and The O.C. 

The whole situation erupts on our narrator’s 30th birthday. (His asshole entourage, naturally, can’t stop assholing long enough to bake him a cake.) At Gatsby’s funeral, Nick realizes that choosing style over substance may win you fans, but not friends—and after the party that was Gatsby’s life, Nick is the only one left with a hangover.

I can’t be the only one who finds it unspeakably awkward that the controversial Daisy Buchanan was based on Fitzgerald’s wife, Zelda. Also that Jordan Baker was named for two car companies in a book where all cars are vessels of evil. This probably speaks for itself in terms of women’s representation—and it speaks volumes about the era.

Will the upcoming movie similarly favor style over substance? Under director Baz Luhrman, probably YES. But maybe that’s exactly how it should be. Money, scandal, sex, murder, drugs… Just add a pregnancy out of wedlock, and Gatsby is a Maury episode waiting to happen.

Is It One of the Greatest Books of All Time?

It has GREAT in the title. This is not a world of subtlety.

Favorite Quotes:

And so with the sunshine and the great bursts of leaves growing on the trees, just as things grow in fast movies, I had that familiar conviction that life was beginning over again with the summer.

I couldn’t forgive him or like him, but I saw that what he had done was, to him, entirely justified. It was all very careless and confused. They were careless people, Tom and Daisy—they smashed up things and creatures and then retreated back into their money or their vast carelessness, or whatever it was that kept them together, and let other people clean up the mess they had made.

Read: 2003 maybe? Or 2005?