Tales from the Jazz Age by F. Scott Fitzgerald
If none of the previous takes the edge off your Gatsby enthusiasm, you might just need another strong hit of Fitzgerald. We prescribe his book of short stories Tales from the Jazz Age, which is essentially an emotional time bomb parading around as a book. You'll get your fill of Fitzgerald standbys, such as deluded flappers, rampant materialism, and how aging is the second biggest bummer of all time (death takes the lead, duh). This collection even has the famous story "The Curious Case of Benjamin Button," which you'll remember was adapted into a 2008 movie starring the Pitt-ster. But for all its gems, we recommend the story "The Lees of Happiness" over everything else. It's our pick for the saddest short story ever written, but you won't be sorry you read it. Not even after you realize you caused a minor flood with your tears.