Infinite Jest

The title is a sly wink at the book's massive girth—it's 1,000-plus pages in most editions—but the reference to Hamlet is well-earned; moreover, it's a damn funny book. The action takes place in Boston at two separate but curiously similar venues—an elite tennis academy and a drug rehabilitation facility—in a near future in which calendar years are available for corporate sponsorship (the Year of the Trial Size Dove Bar, the Year of the Depend Adult Undergarment, and so on). The plot of Infinite Jest—which revolves around, among other things, a lost, unwatchably beautiful art film and a conspiracy among wheelchair-bound Quebecois secessionists—is decidedly secondary to the painfully funny dialogue and Wallace's endlessly rich ruminations and speculations on addiction, entertainment, art, life and, of course, tennis