If we're doing primarily fiction, here's mine:

The Great Gatsby by F. Scott Fitzgerald - American rendition of the Aussie/Brit concept of "the tall poppy syndrome"

The Sun Also Rises by Ernest Hemingway - The joys and sorrows of manhood as exemplified in Jake Barnes who has lost his in WWI

Tender is the Night by F. Scott Fitzgerald - Love, sacrifice, control, and eventual loss. Everything you can say about the relationship between a man and a woman

On the Road by Jack Kerouac - Purest expression of post-WWII America and the beat generation with an exuberance for living and loving

The Razor's Edge by Somerset Maugham - The antithesis of the 30 year fixed, 2.1 kids in an SUV, Pleasant Valley Sunday set