Like many people, I first read The Great Gatsby when I was too young to understand it. I appreciated the beauty of Fitzgerald's prose and his gift for describing scenes, but disliked quite a few of his characters and couldn't fathom why they inspired in each other the degree of devotion and obsession that they seemed to do. I also found the narrator a bit dull and the ending a huge let-down. In short, I was convinced Fitzgerald was a good writer (I actually went on to check out some of his short stories immediately afterwards), but couldn't see what all the Gatsby fuss was about.
I think I can see it now, having reread the book a couple of times since then. Yes, it's a novel about the American Dream -- a rags-to-riches story about a poor man who re-invents himself as a mysterious millionaire in hopes of winning the heart of the beautiful rich girl he has fancied ever since they were young. But it's also about the shallowness of that dream, and about the corruption inherent in it -- about the lengths to which people will go for success and acceptance, not necessarily in an admirable way. It's about the gap between dreams and reality, between reality and perception, and about how modern, status-obsessed America is increasingly on the perception side of the gap. It's an indictment of materialism, of the thin veneer of wealth which hides the moral decay underneath. And last but not least, it's a story about what makes us who we are. About how we are shaped by our pasts and backgrounds, and how, no matter how far we run and how hard we try to re-invent ourselves, we are what we are, what we always were. It's a depressing message for the would-be self-improvers among us, but a true one, I think.
Of course, the book also works on a shallower level. The Gatsby-Daisy romance is fascinating, even if both of its protagonists ultimately turn out to be rather vapid and deluded. And Gatsby's dream is nothing if not powerful. If it ends up failing, that's because it was based on wrong assumptions -- assumptions arising from ignorance and greed as well as hope. There's a lot of greed and ignorance in the book, and it makes for memorable (albeit heavily flawed) characters. (I actually believe Jordan Baker is the most interesting character in the book. I'd have loved to see a bit more of her, although I guess it's precisely her elusiveness which makes her so fascinating.) For his part, old-fashioned Nick proves to be an excellent narrator, whose 'provincial squeamishness' adds just the right kind of perspective to all the modern goings-on described in the book. Nick may be unspectacular and unreliable, but to my mind, he's one of the best narrators in the history of modern fiction. Now that I've learnt to appreciate the novel, his disappointment and disillusionment will stay with me for ever, as will his sad resignation. (If, in fact, that is what it is. One never knows with this endlessly subtle novel.)