In an age of Wall Street riots, pizza-shucking politicians, and the generally chaotic atmosphere of the universe, we’ve decided to compile a list of the Top Ten Funniest Books of All-Time. Consider this list cheaper than Prozac.

The criteria? Gut-splitting, eyes-watering, holy effing-you-know-what-I-can’t-believe-it funny. You know what we’re talking about here. These are the ones where we’re laughing out loud on the subway and people are staring at you because they think you’re insane.  Now, lists like this are, by their very definition, always going to leave out some books, so in the spirit of spreading funniness (ouch), please let us know which books we’ve left out, so that we might create a list of Honorable Mentions. Without further ado, let’s talk about book number ten.

10. Jesus’ Son: Stories

Where to start with this dirty realist classic? How about with “Emergency,” which is probably the funniest thing ever published in the New Yorker, ever. Guy works in an ER, but gets bored, so he takes mushrooms with his coworker just a few minutes before a guy gets admitted to the hospital with a steak knife stuck in the side of his eyeball. Things obviously don’t go well when the drugs kick in, especially when the main character — two hours into the mushrooms — decides to leave work and go for a drive with his buddy, whereupon they find a sack of abandoned little rabbits on the side of the road. Yeah. Ouch. Darkly funny bunny humor ensues. Not for the faint of heart, but more for the Monty Python lovers among you.



Oh, Billy Pilgrim, woe to thee! Vonnegut’s young, essentially normal young protagonist becomes “unstuck” in time, allowing Vonnegut to shift him around from WWII to the future, to the past, to all kinds of compromising and hilarious situations that veer from the insanity of science fiction to the heartbreak of war fiction to the improbably scenes where Billy is encouraged to mate in a futuristic prison cell while the aliens of Tralfamadore watch and scientifically observe his spasmic gyrations. This is another one of those darkly funny books where you sometimes feel guilty for laughing, but can’t help yourself, and you recognize how much pain the author must’ve felt in order to render those emotions — sublimate them, if you will — into this brilliant comedy. (Also, love the subtitle: The Children’s Crusade. WTF?)

8. The Portable Dorothy Parker

To quote: “There’s a hell of a distance between wise-cracking and wit. Wit has truth in it; wise-cracking is simply calisthenics with words.” Another excellent Dorothy Parker quote, which the Literary Lady is fond of retelling in bars. “I always like a good martini, but two at the most; three I’m under the table, four I’m under the host.” Indeed. Here’s to you, Dorothy Parker.

7. HOME LAND by Sam Lipsyte

This novel is a series of rant-like letters written by “Teabag,” the novel’s main character, to his New Jersey high school’s alumni letter. It all starts out harmlessly enough, an update here, a little tirade there, until Teabag’s life sort of starts to fall apart in the vein of the most epic, awkward, trainwreck imaginable. And yet the letters to the alumni magazine keep coming. “I’ve had more flapcandy than you could shake a stick at,” says Teabag’s miserly old restaurant-running father, in reference to what should obviously be a euphemism for the human vagina, when Teabag goes to him for advice about his own failure of a life.  People have compared Teabag’s character to Paul Giamatti in Sideways, but Lipsyte’s writing here is much smarter, much funnier, and much more poetic than anything Hollywood’s sharted out recently.

6. YOUTH IN REVOLT by C.D. Payne

Quintessential hyper-literate novel about being a horny teenager with a horrific family situation. This one falls into the category of cult-favorite, although the recent Michael Sera movie actually wasn’t too bad, and re-ignited interest in this bawdy, SAT-vocabulary boosting brain orgy. Nick Twisp + Sheeni forever!

5. HOLIDAYS ON ICE by David Sedaris

This book is really funny. As in, crying hysterically, can’t get up from the floor from laughing, funny. “SantaLand Diaries” is the best story inside. It’s basically a non-fiction account of David Sedaris’ weeks spent as an elf in Macy’s, in which he is ridiculed and belittled by other elves, as well as the elf overlord. “SantaLand Diaries” is the kind of writing that makes you laugh so hard you wish you were the elf Macy’s having kids piss and shit all over you while you count down the minutes till your next elvin cigarette break. Good stuff.

4. A GOOD MAN IS HARD TO FIND by Flannery O’Connor

Flannery makes the list on the strength of her mind-blowing short story, “Good Country People,” in which an itinerant preacher tries to seduce an overweight, one-legged philosophy grad student who, having failed out of school, has come home to live with her horrifying mother and aunt. Let’s just say this: it isn’t Bibles the preacher has hiding in that briefcase. Oh, no. Definitely not the Good Word of the Lord.

3. LUCKY JIM by Kingsley Amis

Young British college professor fights madly to get tenure at stodgy, prestigious university whilst sleeping with the dean / department chair’s daughter, plagiarizing his academic research, and getting blindly intoxicated before most / all his public lectures. Predecessor of Teabag and other trainwreck literature, in which a lovable / unlovable character has everything possible thing go wrong, delighting the reader every misstep of the way. Takes shadenfreude a whole new level.


Of course, there’s this quote:

“We had two bags of grass, seventy-five pellets of mescaline, five sheets of high-powered blotter acid, a saltshaker half-full of cocaine, and a whole galaxy of multi-colored uppers, downers, screamers, laughers… Also, a quart of tequila, a quart of rum, a case of beer, a pint of raw ether, and two dozen amyls. Not that we needed all that for the trip, but once you get locked into a serious drug collection, the tendency is to push it as far as you can. The only thing that really worried me was the ether. There is nothing in the world more helpless and irresponsible and depraved than a man in the depths of an ether binge, and I knew we’d get into that rotten stuff pretty soon.”

And also this:

Raoul Duke: [Narrating] Ah, devil ether. It makes you behave like the village drunkard in some early Irish novel. Total loss of all basic motor skills. Blurred vision, no balance, numb tongue. The mind recoils in horror, unable to communicate with the spinal column. Which is interesting because you can actually watch yourself behaving in this terrible way, but you can’t control it. You approach the turnstiles and know that when you get there, you have to give the man two dollars or he won’t let you inside. But when you get there, everything goes wrong. Some angry rotarian shoves you and you think “What’s happening here? What’s going on?” And you hear yourself mumbling…
Raoul Duke: Dogs fucked the Pope… no fault of mine.
Raoul Duke: [Narrating] Ether is the perfect drug for Las Vegas. In this town they love a drunk. Fresh meat. So they put us through the turnstiles and turned us loose inside.

1. CATCH-22 by Joseph Heller

Which brings us to the funniest book of all-time.

Here’s one of the earliest reviews: “Catch-22” reviewed by Orville Prescott (1961) ; “‘Catch-22,’ by Joseph Heller, is not an entirely successful novel. It is not even a good novel. It is not even a good novel by conventional standards. But there can be no doubt that it is the strangest novel yet written about the United States Air Force in World War II. Wildly original, brilliantly comic, brutally gruesome, it is a dazzling performance that will probably outrage nearly as many readers as it delights. In any case, it is one of the most startling first novels of the year and it may make its author famous.”

Here’s another one from 1961: “Catch-22” reviewed by Richard G. Stern (1961);
“‘Catch-22’ has much passion, comic and fervent, but it gasps for want of craft and sensibility. A portrait gallery, a collection of anecdotes, some of them wonderful, a parade of scenes, some of them finely assembled, a series of descriptions, yes, but the book is no novel. One can say that it is much too long because its material–the cavortings and miseries of an American bomber squadron stationed in late World War II Italy–is repetitive and monotonous. Or one can say that it is too short because none of its many interesting characters and actions is given enough play to become a controlling interest Its author, Joseph Heller, is like a brilliant painter who decides to throw all the ideas in his sketchbooks onto one canvas, relying on their charm and shock to compensate for the lack of design.”

And this was the line where we probably laughed the hardest:

“I have named our son Caleb, in accordance with your wishes.”

Honorable Mentions:

  • PERSONAL DAYS by Ed Park (thx @andrewbeisenman)
  • CONFEDERACY OF DUNCES by John Kennedy Toole
  • THE CODE OF THE WOOSTERS and QUICK SERVICE by P.G. Wodehouse   (thx @drmabuse)