7 David Sedaris essays to get you ready for his new book ‘Calypso’

David Sedaris has been keeping us entertained, in stitches and tears, for a quarter of a century.
Image: Getty Images

The latest book from writer David Sedaris, Calypso, hits shelves on Tuesday, adding yet another tome to the writer’s stellar collection. The book is his 12th overall, which means that after you’re done, there’s still a whole body of work to continue to explore. 

And, yet, with so many books, essays, and stories circulating from his 25 year career, it can be daunting for both newcomers and long-time fans alike to figure out where to jump in to Sedaris’ stack of writing.

The good new is: No matter where you start, in everything he does, Sedaris’ acerbic humor crackles but it’s not without heart. He has a way of telling stories that can come right up to the line of being mean and then deftly flipping the narrative, revealing a warm core at the center of it all. And, sometimes, his stories even move us to tears.

Whether it’s his early collections, like Naked and Me Talk Pretty One Day, or his more recent reflections in Let’s Explore Diabetes With Owls, Sedaris particular brand of emotional gymnastics is a theme that stretches through all of his work and still remains fresh 12 books later.

But, just in case you need some advice of where to start reading, we’ve collected a few of our favorite essays to help guide you through the wonderful world of David Sedaris.

1. “Santaland Diaries” from various books

The piece that started it all. “Santaland Diaries” tells the tale of Sedaris’ absurdity-filled time as an elf at Macy’s Santa display. And true to form, Sedaris’ recounting is filled with his trademark brand of curmudgeonly humor. The story was first read on NPR in 1992, and an extended version was also read on This American Life and appeared in his books Barrel Fever and Holidays On Ice. “Santaland Diaries” didn’t just give Sedaris his big break (it was adapted into a pretty popular one-man play), it also has become a holiday tradition at NPR

-Marcus Gilmer

2. “Repeat After Me” from Dress Your Family in Corduroy and Denim

Perhaps the pitch-perfect Sedaris essay. “Repeat After Me” is full of laughs as Sedaris explores his sister Lisa’s life — including her parrot Henry — in his typical deadpan style. But the essay gets a bit meta, addressing the way the family feels about Sedaris’ use of their lives and foibles in his writing. While Sedaris churns chuckles out of Lisa, he doesn’t spare himself, either, especially as the story takes a turn for the serious. By the end, the essay has been flipped on its head, closing on a moment of self-awareness and emotional catharsis that lands a hefty — and totally earned — emotional punch. 

Marcus Gilmer

3. “You Can’t Kill The Rooster” from Me Talk Pretty One Day

Like “Repeat After Me,” “You Can’t Kill The Rooster” explores Sedaris’ relationship with one of his siblings. But unlike “Repeat,” “Rooster” keeps things much lighter due in large part to the personalities involved. The Rooster of the title is actually Sedaris’ youngest sibling, little brother Paul, who was born in North Carolina (unlike the rest of the kids) and grew to possess some unique Southern eccentricities, both sweet and profane, that Sedaris revels in sharing. Ultimately, “Rooster” doesn’t take the serious turn that “Repeat After Me” does, but it certainly doesn’t lack for warmth, charm, and a resounding sense of familial love. 

-Marcus Gilmer 

4. “Six to Eight Black Men” from Dress Your Family in Corduroy and Denim

One of the fun parts of reading a David Sedaris essay is that you never know what twist or turn will come next as he documents his adventures. In his essay, “6 to 8 Black Men,” Sedaris deconstructs the Santa myth in the Netherlands, which is an already absurd story in and of itself. (For instance, in the Netherlands, Santa travels via boat and white horse, and is accompanied by six to eight black men who used to slaves until slavery was abolished, and now they’re just referred to as “friends.”)

But it’s not just that myth that makes the story so great, it’s Sedaris’ snarky reactions that makes this essay so unforgettable. “I think history has proven that something usually comes between slavery and friendship, a period of time marked not by cookies and quiet times beside the fire but by bloodshed and mutual hostility,” he writes. Ultimately, “6 to 8 Black Men” is the perfect showcase of the signature wit that made David Sedaris a household name. 

-MJ Franklin

5. “Now We Are Five” from The New Yorker

In his essay “Now We Are Five,” Sedaris writes about the death of his youngest sister Tiffany, who died by suicide in 2013. The essay starts off with a typical David Sedaris observation about an awkward situation: “Now, though, there weren’t six, only five. ‘And you can’t really say, ‘There used to be six,’’ I told my sister Lisa. ‘It just makes people uncomfortable,’” he writes.

But what follows is a moving eulogy about the beautiful, complicated, unforgettable life that his sister Tiffany lived. The moving tribute reiterates that humor isn’t what makes Sedaris’ writing great; it’s his heart. 

-MJ Franklin

Listen to the essay here.

6. “The Angels Wanna Wear My Red Shoes” recorded for This American Life.

The joy of reading David Sedaris is way you experience a wave of epiphanies as you pour through each his humorous stories, and “The Angels Wanna Wear My Red Shoes” is no exception. “Red Shoes” is a short essay about Sedaris trying to explain the insane traditions of our culture — like the Easter bunny — to a beginners French class. In just a few short pages, Sedaris will have you cracking up profusely and leave you with a smile on your face as his limited French language skills create confusion when he shares the tradition with classmates who are unfamiliar with the character.

You can hear him read the story here for the City Arts and Lectures audience in San Fransisco. 

Martha Tesema

7. “Letting Go” from The New Yorker

In “Letting Go,” Sedaris explores his relationship with his mother through the lens of their shared smoking habit. It’s a short story regarding his views on the act, but in his usual hilarious way, Sedaris breaks down the minute process of cigarette selection, what runs through his mind during smoking sessions, his uncle’s death from lung cancer, and the specter of his mother’s hauntingly similar cough. It’s electric writing about something that might seem so mundane if it was penned by anyone other than the brilliant Sedaris. 

You can read “Letting Go” here

-Martha Tesema

These essays are just a start, just a few examples of Sedaris’ deep — and growing — pile of work so there’s much more to dig through if you like what you’ve read here.

Happy reading.

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