My Five Favorite Short Stories

A countdown of my personal favorites following a month-long study of the form.

Spencer Baum
5 min readApr 13, 2018

This March, on Deep Thinking About Great Books, we studied 24 of the greatest short stories ever written.

We read stories by Hawthorne, Faulkner, Hemingway, Steinbeck, Twain, Oates, and more.

Here is a countdown of the five stories I enjoyed most.

#5: The Yellow Wallpaper by Charlotte Perkins Gilman

The Yellow Wallpaper was published in 1892 in The New England Magazine

“It is very seldom that mere ordinary people like John and myself secure ancestral halls for the summer.”

The Yellow Wallpaper tells the story of a woman whose controlling husband has convinced her she is mentally unwell and in need of a “rest cure.” He takes her to the country and puts her in an upstairs room of an old house where her under-stimulated mind develops an unhealthy obsession with the strangely patterned wallpaper.

As the story progresses, our narrator starts to hallucinate, and in the story’s final pages, the narrator’s hallucinations are interspersed with her manic thoughts in a barrage of one-sentence paragraphs, the whole of it creating a visceral first-hand experience of madness.

#4: Going to Meet the Man by James Baldwin.

Going to Meet the Man was published in 1965 in a short story collection of the same name.

Going to Meet the Man is a story, told in flashback, about how an act of horrific ritualistic violence transforms an innocent child into a hateful bigot.

It’s one of the most gruesome and difficult stories in American literature, but it’s essential. Going to Meet the Man is a demand that Americans confront their own history, and a visceral reminder of the violence humans are capable of.

It’s also about the loss of innocence. In the story’s beginning, we view the main character as a villain unworthy of any sympathy. But as the story continues, we see that it’s more complicated than that, especially when Baldwin gives us a description of the world through a child’s eyes as his parents make him watch a brutal execution.

#3: The Smoker by David Schickler.

The Smoker is anthologized in the book Kissing in Manhattan.

“Douglas Kerchek taught twelfth grade advanced placement English at St. Agnes High School, on West Ninety-Seventh and Broadway, and Nicole Bonner was the standout girl in his class.”

The Smoker by David Schickler appeared in the New Yorker in June 2000. Its tight, witty writing, it’s off-the-wall surprises, and its general air of anarchy made it an instant smash.

I love The Smoker because it is humorous and odd, but also ridiculously compelling. As the story unfolds, the sheer audacity of the surprises that the author rolls out for us wowed me. This story has nothing profound to say about life and doesn’t try to punch you in the gut. It merely wants you to have fun reading it, and you will.

#2: The Lottery by Shirley Jackson.

The Lottery was published in The New Yorker in 1948

“The morning of June 27th was clear and sunny, with the fresh warmth of a full-summer day; the flowers were blossoming profusely and the grass was richly green.”

The Lottery by Shirley Jackson is about a strange ritual in an American small town. The townsfolk gather and heads of households draw slips from a ballot box.

Jackson gives us clues that something serious and dreadful is afoot, but forces us to keep reading to find out what it is.

Reading The Lottery is a profound experience in anxiety and dread. It is also a wake-up call that we humans can easily be coaxed into doing horrible things when we are members of a unified group, things we would never do as individuals.

The Lottery is, in many ways, the most terrifying story I’ve ever read, because, by the end, I absolutely believed this could be real.

#1: The Swimmer by John Cheever.

“The pool, fed by an artesian well with a high iron content, was a pale shade of green.”

The Swimmer by John Cheever was first published in 1964. The story immediately became an object of fascination in literary circles for its surprising blend of realism and surrealism and the emotional punch it delivers. It was adapted into a movie starring Burt Lancaster in 1968.

“The sun was hot. Neddy Merrill sat by the green water, one hand in it, one around a glass of gin.”

I was absolutely floored by this story. This truly is a magnificent work of art. The Swimmer is my new answer to the question, “What’s your favorite short story?”

In The Swimmer, a man is enjoying a lazy afternoon by the pool at a neighbor’s house when he realizes that he can map a kind of river of swimming pools in his mind, a river that leads all the way back to his home.

He names the swimming pool river Lucinda, in honor of his wife, and begins traveling it.

“The day was beautiful and it seemed to him that a long swim might enlarge and celebrate its beauty.”

The way this story starts out in the real and travels into the surreal, the way a journey through a neighborhood becomes an imaginative adventure worthy of an explorer crossing the ocean or charging into outer space, the way his neighbors become the inhabitants of faraway and new lands, people that must be treated with respect because he is a guest on an adventure, one who requires their hospitality…

And then how the story changes…

The Swimmer starts out so promising and full of hope, but things start to change. The pools get colder and harder to swim through. The neighbors become less friendly. A storm passes through.

By the end of the story, you realize the journey is nothing like what you thought it would be when it started, and that you’ve been reading a story about nothing less than life itself.

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Spencer Baum

On Medium I write about great thinkers and big ideas with a focus on classic literature. spencerbaum.net