The 10 Most Devastating (and Funny) Books of All Time

A few nights ago I was reading a conversation about humor in fiction in the current issue of Gulf Coast. The title, “I Start From a Place of Outrage and Sadness,” is taken from a response Elisa Albert gives to a question about when, in the writing process, humor works itself in. Rarely do you get writers agreeing about anything, but when asked this question, all the writers (Albert, Steve Almond, Sam Lipsyte, John McNally, and Deb Olin Unferth) generally agree that humor allows us to travel beyond fear. Lipsyte writes that humor is “a sensibility that enables everyone involved to go places (usually forbidden places) they couldn’t get to otherwise.”

My own favorite books are simultaneously devastating and wickedly funny, and I think a large part of this is dictated by my desire to go somewhere I usually can’t in a genuine way, in a way where I choose to go and to struggle through simultaneous layers of meaning that cannot ever effectively be distilled down into one thing. Nothing that is felt strongly is unequivocably made of one emotion or one knowledge base and humor allows readers to remember that, and to see themselves as both insiders and outsiders, as people who sometimes get the jokes and are sometimes the butt of them. This confusion doesn’t mean there is an ambivalence about the real, important issues that these works confront. The funniest, most devastating novels lay bare social, racial, and economic injustices in very straightforward ways. The ambivalence lies in how we are to go about living with these injustices, about what happens when we struggle to right them, or ignore them, or to think up some Jerzy Kosinski  Cockpit plan to just take some people out.

After two days of soul searching and looking through all my bookshelves, I’ve compiled a top ten list of books that are devastating and also funny. The books are in no particular order, although since Don Quixote is the best book of all time (sometimes Harold Bloom is right) it is in the first-spot position on my list as well. I could spend a lot of time talking about each book individually, but really, if you haven’t read them, you should just go do that. I’m sure there are books that might deserve a space in this top 10 that aren’t here (though I’d be hard pressed to take any of these off)–feel free to rant or add. Again, these are the qualifications: Devastating first. Funny second. (although often when reading such books for the first time the order of which you notice these two things is backward). I fully realize this list is probably too American-heavy, and am really bummed that Flannery O’Connor is the only woman on the list. Are there any readers out there who can persuasively fix that?

Don Quixote

Don Quixote Cover


2666 Cover

Fear and Loathing in Las Vegas

Fear and Loathing in Las Vegas Cover


Watt Cover

Adventures of Huckleberry Finn

Trout Fishing in America

Richard Brautigan's Trout Fishing in America, the Pill Versus the Springhill Mine Disaster, and In Watermelon Sugar Cover

The Metamorphosis

The Metamorphosis (Bantam Classics) Cover

A Good Man is Hard to Find

A Good Man is Hard to Find and Other Stories Cover

John Henry Days

John Henry Days Cover

The Tin Drum

The Tin Drum Cover


7 thoughts on “The 10 Most Devastating (and Funny) Books of All Time

    • ha, Danielle. Sometimes things just don’t need to be fixed. Saunders is a great writer. Sometimes I wish his writing was more vulnerable though–that sometimes the satire eclipses the heart. I’m going to pick Civil War Land back up and take another look…

      • The stories are definitely not all equally heartbreaking. Not positive about my memory here, but I think “The Wavemaker Falters” was a killer.

  1. Great List! ‘2666’ is my favorite novel of all time. ‘A Confederacy of Dunces’ also tops my list. And lately David Rakoff essays have been rocking that line between outrage, grief and humor. Thanks Julie. Vince

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