10 of the Funniest American Essayists of Our Time

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Like many of you, this week we were saddened to hear of the death of phenomenal and darkly comic essayist David Rakoff, who had been battling cancer for many years. To celebrate his life and the great literature he left us with, we’ve put together a list of some of the funniest modern essayists, who like Rakoff, are following in the giant footsteps of Mark Twain, Dorothy Parker and James Thurber as America’s great humorists. We’ve tried to limit ourselves to purely contemporary writers, but since we’ve lost several hilarious and essential voices all too recently, we’ve cheated just a bit. Read through our list after the jump, and since these are only our personal preferences plucked from a very long list, be sure to add your own favorites in the comments.

David Rakoff

Rakoff was probably the most melancholic comedy writer of this or any time, his essays often as charmingly cranky as many of his peers’, but laced with a deeper, if lightly applied, sadness that made even the funniest hit home, especially when he wrote about his real life struggles with cancer. As Hilton Als reflected at Page-Turner , “[Rakoff’s work] combined the best aspects of reporting—a gimlet eye and an open heart—with a philosophical point of view that skipped ahead of any claim of self-indulgence.” He will be missed.

Recommended Reading: Half Empty

Nora Ephron

Another recent loss to the American humorist landscape, Nora Ephron, who passed away in June, remains one of our all-time favorites. Smart as a whip, hilarious, and honest to a fault, the essayist, playwright, screenwriter and film director was brought up to believe that “everything is copy” — and boy, has she used everything. “I can’t understand why anyone would write fiction when what actually happens is so amazing,” she wrote. “When you slip on a banana peel, people laugh at you,” she explains. “But when you tell people you slipped on a banana peel, it’s your laugh.”

Recommended Reading: I Feel Bad About My Neck

David Sedaris

Perhaps the undisputed king of this genre, Sedaris’s funny, self-deprecating essays and auto-biographical stories have vaulted him to his current household-name status — and with good reason. Devastatingly hilarious and sneakily incisive, he’s one of those writers that anyone — gender, sexuality, life choices notwithstanding — can manage to see themselves within. Which makes everything he says all the funnier (and more upsetting).

Recommended Reading: Naked , “What I Learned

George Saunders

Though George Saunders is perhaps slightly better known for his short stories than his essays, we think his nonfiction is just as perceptive and witty — and yes, just as funny — as his fiction. It’s even funnier, perhaps, because it’s true — Saunders, perhaps better than any other writer working today, is painfully tuned to the dark comedy of the modern age.

Recommended Reading: The Braindead Megaphone

Augusten Burroughs

Though Burroughs markets much of his work as “true stories,” we’ve always considered him an essayist. His writing, often compared to Sedaris’s, is just as honest, but possibly even more revealing of the darker impulses in the human psyche — or maybe it’s just that Burroughs is a few clicks more caustic than Sedaris. Either way, his cynical, one-eyebrow raised observations are sure to make anyone whose ever had a dark thought laugh — or maybe just hack guiltily into their coffee.

Recommending Reading: Magical Thinking

Meghan Daum

A shrewd and very funny analyst of American culture, Daum’s first collection of essays is a meditation on “the tendency of contemporary human beings to live not actual lives but simulations of lives, loving not actual people but the general idea of those people, operating at several degrees of remove from what might be considered authentic if we weren’t trying so hard to create authenticity through songs and clothes and advertisements and a million other agents of realness.” That sounds serious, and it is — but it also isn’t, rendered in Daum’s clever, compelling storytelling style. And after all, Americans laughing at their own American-ness is something we can always use more of.

Recommended Reading: My Misspent Youth

Steve Martin

Steve Martin is a man with his hand in just about everything: actor, playwright, producer, musician, author, essayist, comedian — the list (probably) goes on. But no matter what he does, he’s hilarious at it. So as far as we’re concerned, he can keep on finding new ways to make us laugh forever.

Recommended Reading: Cruel Shoes

Sarah Vowell

A contributing editor for This American Life, Vowell consistently stretches her dry wit to take on every corner of her country’s past and present — from Teddy Roosevelt to Buffy the Vampire Slayer. Clever, critical, and possessing a voice that is very much all her own, anyone interested in the state of the union will get a kick out of this lady.

Recommended Reading: The Partly Cloudy Patriot

Sloane Crosley

The lovely, NYC-publicist wunderkind Crosley is oft-hailed as the female David Sedaris — and we can’t say we disagree. Possessed of the same self-deprecating, inclusive humor and penchant for storytelling, reading her essays is like sitting around with your best friend since you were four — no secrets, no shame, no holding back. Which, as you can imagine, is pretty damn funny.

Recommended Reading: How Did You Get This Number

Gore Vidal

Yet another recent and tragic loss to American letters, we refer you to this list of the literary giant’s best zingers. You’re welcome.

Recommended Reading: The Selected Essays of Gore Vidal