Not to get too philosophical, but it’s hard to define what is truly funny. Is it something that has you falling on the floor laughing or something that has you chuckling inside while also pondering the absurdity of the human condition? What each of us defines as funny depends on the individual subject: some of us might think there’s something funny about The Stranger by Camus, while others prefer Adam Sandler making fart sounds. The point is that humor works as a device that can make you laugh with reckless abandon, but also ponder this strange situation we call life. Not everything that’s funny has to start off with “Knock knock,” and these 25 books offer an opportunity to see how writers have used humor in different ways, to often-brilliant results.
A Confederacy of Dunces, John Kennedy Toole
Remember your college significant other that kept telling you that you had to read this book? You know the one I’m talking about: the one with bad taste disguised as pseudo intellectualism. Yeah, that one. A Confederacy of Dunces was really all they got right (except for you, of course) in terms of things they suggested you check out, because the story of Ignatius J. Reilly, our modern Don Quixote, is one of the funniest and finest American books of the the 20th century.
Woke Up Lonely, Fiona Maazel
The blurb says Maazel’s second book is about “loneliness in America, North Korea, espionage, a city underneath Cincinnati, cloud seeding, and eavesdropping. It’s also a big, sweeping love story.” And while that’s all true, Maazel balances it all out with a dark strain of humor that is pretty hard to miss throughout this brilliant book.
The Little Disturbances of Man, Grace Paley
Clever and funny aren’t the same thing, but they run in the same circles. That’s what Paley’s writing teaches us over and over in her stories. The Little Disturbances of Man isn’t here because Paley wrote her books to make you laugh out loud, but her genius will always make you smile.
The Stench of Honolulu, Jack Handey
One of the great comedy minds of the last few decades took a long time to get around to writing a novel, but when he finally did it last year, it got us thinking that we could be in the middle of a comedic literature boom.
The Ask, Sam Lipsyte
Lipsyte might be the contemporary American writer who best understands how to balance humor with great writing. While his short stories might get the job done faster, and might have you feeling a little more terrible about laughing, The Ask is his masterpiece — a novel that somehow finds a way to perfectly skewer American culture in the second decade of the 2000s.
White Noise, Don DeLillo
When you hear that the themes from DeLillo’s breakthrough novel include consumerism to obsessing over death, you might not automatically think that sounds funny. Then you read it, find yourself cracking up because the idea of somebody making Hitler Studies (without knowing any German) their life’s work, and start to recognize just how brilliant White Noise is.
Portnoy’s Complaint, Philip Roth
There isn’t much we can really say about this one, except that when you hold it up against Roth’s later work, nothing reads like it was written with the intention of making people laugh.
Dead Souls, Nikolai Gogol
The hilarity begins with the title. You think Gogol’s famous work is going to be this creepy gothic masterpiece, then you open it to find out it’s a hilarious and weird satire exploring things Gogol saw wrong with Russia in the 19th century.
Metropolitan Life, Fran Lebowitz
Even though she’s still dealing with writer’s block, Lebowitz is still the humorist version of a New York poet laureate. This 1978 collection of essays shows why.
The Most of S.J. Perelman, S.J. Perelman
The great Perelman. Was he a modernist disguised as a humorist? Was he a humorist who showed how funny modernists could be? Maybe both, maybe neither. But as an American situated somewhere between James Joyce and P.G. Wodehouse, a writer who chiseled out every wacky sentence like tiny sculptures, he should be considered among the greats.
Don’t Get Too Comfortable, David Rakoff
We’re still reeling from David Rakoff’s death just a little under two years ago. That great sardonic wit who could put American culture under a microscope (and sometimes that of his native Canada as well), making every ugly little spot hilarious, Rakoff’s place among the greats should be confirmed. We’re pretty sure Don’t Get Too Comfortable is his finest work, but reading all of his books to find out is also a fine idea.
The Great Frustration, Seth Fried
Fried took all the things we love about George Saunders, and he went ahead and made them a little darker. What more could you really ask for?
Gentlemen Prefer Blondes, Anita Loos
We love Gatsby, but we will also suggest the timeless exploits of Lorelei Lee as the great Jazz Age humor novel any day of the week.
Civilwarland in Bad Decline, George Saunders
Since people are all saying he’s our modern American Chekov, it’s really tough to pick just one Saunders collection. But this one, especially with its title story, is a little weirder than the rest.
Heartburn, Nora Ephron
Is this autobiographical novel Ephron’s best work? Hard to say. All we know is there are few people out there that could take a FUBAR situation like a marriage breakdown and turn it into something sweet, sad, and funny. This is one of the many reasons we still miss Nora Ephron.
The Portable Dorothy Parker, Dorothy Parker
This is basically like a bible for people that want to be witty.
Boswell: A Modern Comedy, Stanley Elkin
Elkin doesn’t always get mentioned in the same breath as Roth, Vonnegut, Heller, etc. in terms of great post-war writers who blended humor into their work, but that should really change. Here, with his debut working like sort of a modern Dead Souls update, Elkin started his streak of great, often hilarious books.
Like You’d Understand, Anyway, Jim Shepard
Shepard is this list’s prime example of writers whose brand of humor slowly reveals itself as you keep reading. It isn’t instantly obvious, and it isn’t so much that Shepard is trying to be funny; he just gets the absurdity, the darkness, and the light, and how to turn all of that into near-perfect fiction.
Christmas Pudding and Pigeon Pie, Nancy Mitford
Mitford showed a unique sense of humor reminiscent of Waugh and Wodehouse in her early works, but with a sense of refinement and a feeling that she really knew the kinds of characters she was having a little fun with.
The Dud Avocado, Elaine Dundy
You know the drill: American goes to some big city with dreams of conquest, hilarity ensues. Dundy’s 1958 novel (which had a huge fan in Groucho Marx) is pretty much the best and funniest example of that whole genre.
I Was Told There’d Be Cake, Sloane Crosley
We’re guessing the time will come when the chronic writer’s block will force Fran Lebowitz to give up her post as New York’s greatest humor essayist. While we will be sad when that happens, we’re hoping that Crosley, who has already given us two great books full of hilarious essays, will consider applying for the position.
Carry On, Jeeves, P.G. Wodehouse
The great thing about Wodehouse and his most famous characters is that you know nothing that bad will ever happen to them. It’s just a bunch of bumbling rich English people and the smart butler who helps get his boss out of jams.
Flatscreen, Adam Wilson
All the bored and stoned young men in the world got their patron saint with sad bastard Eli and his misadventures through New England. Few modern novels will have you laughing out loud as much as this debut will.
The Magic Christian, Terry Southern
It feels like we’re days away from a Terry Southern renaissance. Although he’ll probably always be remembered first as the man who helped Kubrick make Dr. Strangelove funny, it was this novel that caught the famous director’s eye in the first place. The Magic Christian is one of the last great novels of the 1950s, and helped usher in the crazy 1960s in style.
The Complete Short Stories of Mark Twain, Mark Twain
It shouldn’t surprise you that father of American humorists also happens to be one of the most important writers this country has ever produced. You can find little bits of humor in all of his work, but start with Twain’s short stories if you really want to laugh.
Log in with Facebook 
