A Confederacy of Dunces – John Kennedy Toole
This has to be one of the funniest works of fiction that I have ever read. Most notably because of its protagonist, Ignatius J. Riley, one of the most obnoxious characters you are likely to run into in literature. He’s highly educated, but that’s about as far as his qualities go. He’s pretentious, arrogant, obnoxious, ill-tempered, hyper-critical and oblivious. If he were a 21st-century figure, he’d be the type who would go into online message board just to engage people in meaningless arguments about topics like The Jonas Brothers or Modern Family, just to make himself feel superior. The plot involves a series of his misadventures populated with a ragtag gang of misfits, each of whom is entirely ridiculous, yet stays just on the right side of being believable. Most of the joy of this novel comes from watching their varied adventures fall apart, and specifically with Ignatius, having that sick sense of joy in watching it happen.