The best books to make you laugh and think

I found Carl Hiaasen’s Skinny Dip while visiting my mother-in-law in Florida. The complex where she lived included a clubhouse that was always empty. Wandering into the small library one morning, my eyes gravitated immediately to Skinny Dip. In the very first paragraph, a woman is pushed from the deck of a cruise ship by her scheming husband. As she plunges toward the dark Atlantic, just off the Miami coast, she thinks, “I married an asshole.” Naturally, I was hooked and spent the next two hours reading half the book. I consider it a special piece of luck to have found Carl Hiaasen and his hilarious cast of Floridian degenerates, weasels, and idiots—and the minority of decent Floridians who must deal with them—while in their backyard. 

Like a lot of people, I came to A Clockwork Orange after seeing Stanley Kubrick’s iconic adaptation, which cleverly incorporates elements of surreal humor into its many disturbing visuals. But the novel, with its groundbreaking use of an invented futuristic slang – Nadsat – is on another level in this regard. Despite the awful acts performed by Alex and his droogs, you can’t help laughing at such phrases as “bolshy groodies,” “starry vellochecks,” “pink glazzies,” and “a malenky bit bezoomny.” The language carries you creeching and smecking through the humble narrator’s descent into state-controlled redemption, all of it real horrorshow and full of joy joy joy, O My Brothers.

If you asked me to name Don DeLillo’s best novel, I would say White Noise. But if you asked me which is my favorite, I would say End Zone. Set in the burning endless space of West Texas, it follows the travails of the Logos College football team. The players are all exiles of one kind or another and find themselves in “the middle of the middle of nowhere, [a place] suggestive of the end of recorded time.” They spend their days crashing into each other at high velocity. Sometimes they fight. In the evenings they pray. DeLillo’s narrative roams the prairie like a tornado, spinning everything it touches into a dizzying mix of philosophy, religion, geopolitics, nuclear war, and of course football, that perfect metaphor for all human conflict, struggle, and joy. 

Pynchon’s most famous tome is one of the 20th Century’s top literary heavyweights, up on the shelf next to Ulysses and To the Lighthouse, and I dove into it as an aspiring literato, eager to add it to my “conquered classics” list. But I was totally unprepared for the novel’s explosive humor. Still one of the funniest books I’ve ever read, it follows the main character, Tyrone Slothrop, through the ruins of war-ravaged Europe, from the rooftop banana farm in London during the V2 rocket attacks, to the Herman Goering Hotel and Casino on the newly liberated French Riviera, to the German rocket factories at Nordhausen, where we learn the secrets behind Dr. Laszlo Jamf’s diabolical Imipolex G. Along the way we meet Roger Mexico and Colonel Ernest Pudding, Darlene Quoad and Geli Tripping, Scorpia Mossmoon and Richard M. Zhlubb, to name a paltry few. Even Mickey Rooney shows up, selling hasish at the site of the 1945 Potsdam conference. Gravity’s Rainbow will blow your mind with the force of a V2 rocket, but you’ll be gut-laughing all the way to your obliteration. 

With great humor and deep empathy, Thomas Berger creates a vision of the Wild West not seen in any John Ford film. The eponymous hero journeys from his pioneer boyhood into the world of the Northern Cheyenne, who, despite slaughtering his family, adopt him as one of their own. There he learns their complicated ways. For example, “[While] Indians love war, … they don’t like to lose relatives to it. They really like one another in the same tribe, and while they hate their enemy, … they don’t want to change him into anything else.” Balanced between the Cheyenne and the ever-encroaching White Man, we travel headlong toward the last great showdown of the untamed West, on the banks of the Little Big Horn.