The top 10 funny books of all time

Widely recognized as one of Western lit’s very first modern satires, Voltaire’s wacky, 1759-published romp takes top honors on this list. An Age of Enlightenment philosopher who was vehemently anti-church and anti-aristocracy, Voltaire slays both in this short-but-sweet novella. Ostensibly the continent-wandering tale of Candide, the illegitimate nephew of a German baron whose unending bad luck forces him into a life of unending roving, the book was actually a very clever—and often uproarious—vehicle for Voltaire’s finely observed criticisms of religion, government, military and, well, most of the other features of 18th-century life: criticisms that still ring true today.

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When it comes to laughing-out-loud-on-the-subway hilariousness, it’s hard to beat essayist, critic and performer Sedaris, whose bestselling collections of personal essays turn self-deprecation into an art form. The 27 short works contained in Me Talk Pretty One Day revolve mainly around Sedaris’ eccentric family, including his famous sister, Amy, as well as time spent living in France, where the author’s grasp of the language evolves from the level of “evil baby” to “hillbilly”: “‘Is thems the thoughts of cows?' I'd ask the butcher, pointing to the calves' brains displayed in the front window,’” he recalls. No matter how depressing the circumstances, Sedaris’ wit elevates such moments with his comic grace and we’re left laugh-crying and scrambling for tissues.

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One of the most celebrated books of all time, Heller’s 1961 satire is as incisive as it is funny—and it’s just as fresh today as it was 50 years ago. Set in Italy during World War II, the novel centers on Yossarian, a wisecracking bombardier whose attempts to complete his increasing—and increasingly perilous—combat missions skewer the madness of war. It’s from the book that we get today’s oft-used, eponymous phrase: In Heller’s work, the “Catch-22” is a completely unexplainable rule instituted by the military bureaucracy which decrees that any soldier willing to complete his ever-more-dangerous missions is insane—but if that soldier recognizes what’s happening and requests a discharge, he’s therefore proven sane and ineligible for release. As Yossarian considers his options, we’re right there with him—and laughing the whole time.

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A rambling farce set on the charming but squalorous streets of New Orleans, Toole’s comic masterpiece introduces us to Ignatius J. Reilly, an unlikely hero who, at the age of 30, lives with his mother and snacks his way to obesity as he attempts to write his magnum opus. A series of unfortunate events force Ignatius to seek employment, and readers follow along as he peddles hot dogs and works in a pants factory, determined to innovate by showing up for work an hour later than he’s supposed to (more refreshed and therefore more productive) and throwing random files into the trash (thus eliminating potential fire hazards). The novel’s true strength lies in its wonderfully 3-D supporting characters, including Miss Trixie, Levy Pants’ septuagenarian secretary whose attempts to retire are continually—and comically—thwarted.

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If your only familiarity with gonzo journalist Thompson’s drug-drenched romp is through Terry Gilliam’s (admittedly brilliant) 1998 film, you’re missing out: the outsider author’s 1971 account of a booze-and-pill-fueled joyride across the Nevada desert is, by turns, terrifying and gut-busting. A based-on-fact recollection of Thompson’s magazine assignment to cover a biker race and convention in Vegas, Fear and Loathing lists, in great detail, the sundry substances responsible for Thompson’s (and his lawyer-pal Dr. Gonzo’s) subsequent sins in Sin City; namely, “two bags of grass, seventy-five pellets of mescaline, five sheets of high-powered blotter acid, a salt shaker half-full of cocaine and a whole galaxy of multicolored uppers, downers, screamers, laughers.... A quart of tequila, a quart of rum, a case of Budweiser, a pint of raw ether and two dozen amyls.” The fact that Thompson remembered enough about the journey to pen the book is reason enough to pick it up; the belly laughs are just a bonus.

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Poehler’s book belongs to a supergroup of candid, witty memoirs and personal essays published in the last few years by brilliant and hilarious women like Tina Fey (Bossypants), Lena Dunham (Not That Kind of Girl) and Mindy Kaling (Is Everyone Hanging Out Without Me?)—and each of these ladies and their careers owe a debt to Ephron. She’s the OG of revealing and riotous writing, and the person whom we collectively must thank for all of When Harry Met Sally and especially that insane pastrami scene. Throughout her long and active career, the recently deceased Ephron was consistently adept at tackling taboo topics, and in I Feel Bad About My Neck she attacks female aging with her usual comic verve, addressing issues such as empty nests, menopause and mature fashion with her inimitable combination of sarcasm and sincerity.

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