This Side of Paradise (1920) was Fitzgerald's first novel. For him it was both a commercial success and a personal achievement: Not only did it give him recognition as an author, but it was enough to get Zelda to believe in him and marry him. To me, however, much of the story is rambling and abstract and the plot is mostly devoid of action. Assuming it's autobiographical though, it is remarkable that he had so many of the same experiences and private thoughts I had growing up. While I didn't share my thoughts with the rest of the world, but if he and I had so much in common 50 years apart, maybe a lot of other people do, too, and that's what makes this book so interesting.
The Beautiful and the Damned (1922) is much longer and rambles more, but the plot has more action and the rambling sections are very descriptive of the 1920's lifestyle. In fact I got so involved with the lifestyle, that, at times, I forgot I was reading a story. What's striking about the lifestyle and the characters are that human nature then was the same as it is today! History changes the world, but our lifestyles only change on the surface. Human nature remains the same. It's notable that Twain, Chaucer, Boccaccio, and even the Bible all show us the same thing: human nature is timeless.
The Great Gatsby (1925) is renowned as Fitzgerald's greatest novel and may in fact be the Great American Novel. It is incredibly succinct. Every sentence is meaningful, descriptive, and actively contributes to the plot. It's obvious he consciously incorporated symbols and metaphors throughout and he addresses many subjects Americans can relate to: dreams, ambition, success, failure, and disillusionment. It packs a lot of substance into a small space, it's easy to read and understand, and, as a bonus, is also very descriptive of the lifestyle of the Roaring Twenties.
Tender is the Night (1934) Many people say this is actually Fitzgerald's greatest novel. I haven't read it yet, but it's on my list.
References:
F. Scott Fitzgerald. This Side of Paradise. Scribner's. 1920.
F. Scott Fitzgerald. The Beautiful and the Damned. Scribner. 1922.
F. Scott Fitzgerald. The Great Gatsby. Scribner. 1925.
F. Scott Fitzgerald. Tender is the Night. Charles Scribner's Sons. 1934.
