The Great Gatsby
The Great Gatsby is the perfect English-curriculum high school book. It's oozing symbolism (with varying degrees of obscurity) and dwells on humanity's innate corruption. In other words, The Great Gatsby gives English teachers plenty to talk about and school boards a warm and fuzzy feeling that they are preparing students for the real and nasty world out there.
It almost goes without saying that The Great Gatsby is also well written and has genuine value. Among other things, the author, F. Scott Fitzgerald, examines how the very rich and selfish can cause terrible events to occur to the people around them. In a society which prides itself on equality, this is a point worth considering. If wealth allows people to dodge culpability, then an equal society does not exist.
The problem with The Great Gatsby is that I don't like it very much. I didn't like it in high school, and I've re-read it twice recently and I still don't like it. I can see it's well-written and well-constructed, it's clever and the author presents ideas that are worth considering. I think where it falls flat with me, though, is that the characters are just not likable.
I mentioned above that Fitzgerald examines how the rich can avoid blame for their actions. People from all economic backgrounds, though, are fairly unlikable in this book. They're selfish, short sighted, petty and narrow minded. Money doesn't make people objectionable in this book; it just gives them more power to be objectionable.
A few of the characters have redeeming features, but the timing and presentation of these more positive characteristics tends to be too little, too late. Gatsby is the obvious example. At least arguably, he does redeem himself, but it's fairly far on in the book before this is revealed. The reader is left flailing through the book, trying to latch onto a character who can represent what is good in a sea of characters who represent what is wrong.
How much this will bother readers, of course, depends on what they think of people in general. A misanthrope would probably think this book is spot on, though would perhaps consider Gatsby's more positive characteristics exaggerated.
Without hesitation, I recommend The Great Gatsby to all misanthropes. To everyone else, it's an interesting read and a very well constructed book.