#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?

#4 The Adventures of Huckleberry Finn, Mark Twain

Cover of "The Adventures of Huckleberry F...

Let’s kick off The 100 Greatest Books Challenge with The Adventures of Huckleberry Finn, or Shenanigans Culminating in a Lesson on Morality. I couldn’t tell you how many times I’ve read it, but I know it’s never been by choice. That’s how famous—and how frequently assigned—this 1885 novel is.

It’s rough going, here and there—I wouldn’t pretend otherwise. Something about the zigzagging plot and recurring dialect has always bankrupted my patience. But the heart of its message and its main characters is too close to my own to ignore. So even as the ADD plot inflicts repeated whiplash, I still enjoy the ride.

Every. Single. Time.

Mark Twain’s literary legacy—a masterful combination of irony and social criticism—remains alive and well, despite his preposterous mustache. He had a zero tolerance policy for racism and stupidity—and you can’t be that witty in life or in print without making a few (million) fans. If you’re among them, consider taking a Huck Finn-themed riverboat ride on the Mississippi. Because, yes, that exists in our absurdly awesome world.

This is a book that will make you weep weepy tears… whenever you manage to follow along. A triumph of critical thinking over society’s chronic brainlessness, Huckleberry Finn is best known as the quintessential bildungsroman.

Whatever that is.

Is It One of the Greatest Books of All Time?

Abso-Hucking-lutely.

Favorite Quotes:

Jim said that bees won’t sting idiots, but I didn’t believe that, because I tried them lots of times myself and they wouldn’t sting me.

If you tell the truth you do not need a good memory!

I was a-trembling, because I’d got to decide, forever, betwixt two things, and I knowed it.

Read: 2003, 2005, 2007, and so on