• "Happy Endings" - Margaret Atwood
    • This brief bit of delightful metafiction opens with the meeting of two characters named John and Mary, then offers up a series of potential endings to their story. Atwood uses these endings (much like Ursula K. Le Guin in "The Ones Who Walk From Omelas") to comment not only on the constructed nature of storytelling, but on the constructed nature of modern life and our distorted definitions of happiness. 
  • "An Occurrence at Owl Creek Bridge" - Ambrose Bierce
    • Bierce's story of a man being hanged during the Civil War will probably come across lazy or cheap to modern readers—its particular narrative choices have since come into and gone out of fashion—but it is still remarkably effective in its ability to warp time and sense perception through language in order to create heightened drama. This is one of the most iconic gut-punches in the canon of short fiction. 
  • "macs" - Terry Bisson
    • The premise is simple: in the wake of a bombing clearly inspired by Oklahoma City, 167 clones of the bomber are created and sent to the families of the 168 victims to do with as they wish...and one family receives the actual bomber. But which one? There's no way to tell. "macs" is an extraordinary meditation on the meaning of justice, punishment, and vengeance through a science-fiction lens. 
  • "They're Made Out of Meat" - Terry Bisson
    • Comprised of nothing more than a dialogue exchange between two aliens debating whether they should make contact with humans, "They're Made Out of Meat" is a sobering bit of existential humor that would make Douglas Adams proud. It's worth re-reading regularly to put things in perspective. 
  • "All Summer in a Day" - Ray Bradbury
    • Bradbury is a master of short form storytelling, and "All Summer in a Day" is one of his besta singularly perfect tragedy that will break your heart in half. I don't want to say too much in the way of specifics for fear of lessening the impact of the story, but suffice to say that this is a must-read. 
  • "There Will Come Soft Rains" - Ray Bradbury
    • It's a testament to Bradbury's talent that this story works at all—there are (arguably) no characters to speak of, no plot or semblance of a narrative. But to describe it as a mood piece or an exercise in worldbuilding, even though it is those things, is also not accurate. "There Will Come Soft Rains" is a mournful unveiling; the arc of the story happens in your mind as you slowly come to understand the events that preceded it. It's an exquisitely sad piece of work, but, in its own devastating way, peaceful. 
  • "The Sound of Thunder" - Ray Bradbury
    • This classic Bradbury tale is cliché by contemporary standards, but there are few finer examples of time travel and the bufferfly effect in the realm of short fiction. Utilizing his sharp writing and efficient storytelling, Bradbury misdirects your sense of tension—until he blindsides you with the chilling ending.
  • "The Veldt" - Ray Bradbury
    • "The Veldt" is a singularly terrifying piece of work that will require you to take a leap of faith in your suspension of disbelief. The story flirts with triteness enough for me that it becomes grating (especially near the end), but the emphasis on two major satirical prongs rather than one lends it the richness it needs to become memorable. Despite my misgivings, "The Veldt" is a classic that's well worth reading. 
  • "The Story of an Hour" - Kate Chopin
    • "The Story of an Hour" sits comfortably alongside "The Yellow Wallpaper" as one of the all-time classic examples of feminist short fiction; in this tale, a woman experiences unexpected excitement upon learning that her husband has died. It's a subtle, challenging, sophisticated piece of work that has yet to lose any of its hypnotic and discomforting relevance. This is one that you really, really need to read. 
  • "This is Moscow Speaking" - Yuli Daniel
    • Before The Purge, there was "This is Moscow Speaking," a piece of samizdat literature from the USSR featuring a similar premise: a temporary period in which crime is made legal. The direction the story takes reveals much about the difference between Soviet Russia in the 60s and America in the 2010s (guess who gets the more favorable portrayal), and Daniel's choice to keep his work focused on only a few people exponentially amplifies the weight of the drama in the midst of a premise of such scale. 
  • "The Deathbird" - Harlan Ellison
    • "The Deathbird" is usually pitched somewhere along the lines of "What if the devil got a bad rap because God was in charge of PR?", and Harlan Ellison does more with this premise in thirty pages than most writers could in three hundred. It's a sprawling narrative that spans thousands of years and plays with a variety of narrative tricks; there are few stories as thematically dense, as ambitious, or as utterly unorthodox as "The Deathbird." It's one of the greatest pieces of short fiction ever written. 
  • "The Yellow Wallpaper" - Charlotte Perkins Gilman
    • A landmark text for both feminism and psychological horror, "The Yellow Wallpaper" is a story that doesn't sound particularly compelling—a woman sits in a room and stares at the yellow wallpaper while her mental state deteriorates—until you read it. It creeps under your skin and festers there; the terror somehow seems to amplify the further you get from the story. Chilling and essential. 
  • "Hills Like White Elephants" - Ernest Hemingway
    • I like to hate on Hemingway, but there is perhaps no better example of his utter storytelling mastery than "Hills Like White Elephants." Told almost exclusively in sparse exchanges of dialogue, Hemingway uses the words on the page to squeeze rich characterization, backstory, and suffocating tension from the space between the lines. It's a dizzying display of talent from an undisputed master of literary craft. 
  • "The Harvest" - Amy Hempel
    • A knot of unreliable narration that spins you around and around and around (and around and around and around), Amy Hempel's "The Harvest" challenges you to decipher the truth at its core with hardly any firm ground to stand on. Playful and frustrating, "The Harvest" is metafiction at its absolute best. 
  • "The Gift of the Magi" - O. Henry
    • A piece of literary clockwork that perfectly threads the needle between depressing and heartwarming, "The Gift of the Magi" is pure magic. Its twist ending is now all but common knowledge, but that shouldn't deter you from reading—Henry's work is deeply elegant in its low stakes and tight focus. 
  • "The Lottery" - Shirley Jackson
    • This is the short story to end all short storiesattend any high school English class in America and "The Lottery" will almost certainly show up on the syllabus. It's with good reason: Jackson's story is one of the most finely-crafted pieces of literature you'll ever read, a bone-chilling tale that never loses its edge no matter how many times you encounter it. A timeless piece for its satire and deeply human core. 
  • "Spar" - Kij Johnson
    • "Spar" is the only story I have ever read that consistently provokes a truly visceral response; it was my first encounter with Kij Johnson, and I was so revolted that I stopped reading and didn't return to the story for years. What a shame! Johnson is at the height of her wordsmithing powers in this tale of a woman stranded aboard a spaceship with an amorphous alien that continually rapes her. It's a challenging but worthwhile read, a testament to the power of discomfort in literature. 
  • "The Man on the Stairs" - Miranda July
    • As bitter as it is brief, Miranda July's "The Man on the Stairs" brings you into the mind of a woman waiting restlessly in her bed while ominous footsteps ascend the steps in her home. "The Yellow Wallpaper" and "The Story of an Hour" echo in the subtext as the woman descends in paranoia, and the note on which the story concludes is just asif not morehaunting than its predecessors. 
  • "Flowers For Algernon" - Daniel Keyes
    • Daniel Keyes' novel of the same title is probably more famous than the "Flowers For Algernon" short story, but it still packs quite a punch in its condensed form. It's the simple epistolary chronicle of a man who undergoes an experiment which drastically but temporarily increases his intelligence; his awareness of himself and his surroundings becomes clear through the evolution of his word choices and syntax. There are few better examples than this story of the power that science fiction can have. 
  • "The Ones Who Walk Away From Omelas" - Ursula K. Le Guin
    • It isn't entirely a stretch to say that "The Ones Who Walk Away From Omelas" is one of the pillars upon which modern dystopian fiction was built. Stripping the "ends vs. means" theme down to its core and engaging in one of the most morally-challenging meta-narratives I've ever seen in a work of short fiction, this is Le Guin at her most deceptively powerful. A masterful story from a masterful storyteller. 
  • "To Build a Fire" - Jack London
    • Strangely subversive in its lack of a twist, "To Build a Fire" relentlessly chronicles the struggles of a man attempting to make a journey through the wilderness in an extremely cold environment; one by one, things begin to go wrong, and he must face the possibility that he will succumb to the weather. Simple but shockingly effective, "To Build a Fire" showcases Jack London's strong short-form storytelling. 
  • "The Call of Cthulhu" - H.P. Lovecraft
    • Arguably more important in the 21st century for its meteoric cultural impact than its actual merits as a piece of literature (although it's still a damn fine story), Lovecraft's "The Call of Cthulhu" features his iconic cosmic horror in the form of the titular Cthulhu, an eldritch entity sleeping in the undersea city of R'lyeh. This is an ideal entry point for getting into Lovecraft: it's not too long (his prose is dense and can feel oversaturated), not too short, and makes use of his most common and effective tropes. 
  • "The Things They Carried" - Tim O'Brien
    • "The Things They Carried" is the first story in the eponymous collection by Tim O'Brien, a monumental work of literature about the Vietnam War. It is, quite simply, a list of the physical and emotional baggage carried by each of the soldiers in the tale. O'Brien's specific and evocative prose—and more importantly, the transition from physical to emotional baggage, from ammo to memories, over the course of the story hammers it home as one of the all-time great works of short fiction. 
  • "A Good Man is Hard to Find" - Flannery O'Connor
    • It's so much more difficult to talk about something you love than something you hate. Flannery O'Connor's "A Good Man is Hard to Find" is one of my all-time favorite short stories (it's a classic, too), and it's hard to explain why: there are so many layers of allegory and metaphor and theme and subtext, and I find that I am rewarded with additional personal and literary insight every time I read it. It's a prism, a puzzle box, a comedy and a satire and deeply truthful work that cuts deep into your bones. 
  • "Guts" - Chuck Palahniuk
    • In typical Chuck Palahniuk fashion, "Guts" is a gloriously over-the-top horror story about a boy who becomes suctioned to the bottom of a pool while masturbating underwater. Palahniuk's tight, twisted prose and careful attention to structure will leave you breathless, and the ending of the story is a perfect "gut"-punch (see what I did there?) that will make you laugh and squirm in all the right ways. 
  • "The Cask of Amontillado" - Edgar Allan Poe
    • I don't believe "The Cask of Amontillado"'s status as part of the canon is questionable, but I'm not entirely sure whether it belongs more on the basis of its merits as a piece of literature or more on the basis of its place in pop culture. It's a good story that relies a bit too heavily on the shock of its ending and has less to say thematically than other Poe tales like "The Masque of the Red Death" or "The Tell-Tale Heart," but it's still a viciously visceral work that is supremely discomforting to read. 
  • "The Masque of the Red Death" - Edgar Allan Poe
    • The premise is simple: a group of people lock themselves in a castle in an attempt to protect themselves from a disease called the "Red Death"—and, predictably, things don't go according to plan. Soaked through with (literally) colorful symbolism, "The Masque of the Red Death" abandons the psychological horror of many of Poe's other classics ("The Fall of the House of Usher," "The Tell-Tale Heart") in favor of existential horror. The result is a truly chilling and unforgettable piece of work. 
  • "The Tell-Tale Heart" - Edgar Allan Poe
    •  "The Tell-Tale Heart" is obviously one of the most famous short stories ever written, so of course it has a place on this list. Poe's masterpiece about the suffocating relentlessness of guilt is so perfectly conceived, so effortlessly executed, that it has retained its power across the years and remains as thrilling to read today as it must have been when it was originally written. This is a true classic. 
  • "Harrison Bergeron" - Kurt Vonnegut
    • Vonnegut hits the "equality vs. individuality" theme a bit hard in "Harrison Bergeron," but it remains an immensely challenging story in its deconstruction of values that we have so long accepted as inherent in the Western world. The dystopian society of "Harrison Bergeron" forces its citizens to endure handicaps which (supposedly) make them equal to one another, and it's so absurd that it works. 
  • "Bullet in the Brain" - Tobias Wolff
    • Few stories celebrate the wonder of words as eloquently as Tobias Wolff's "Bullet in the Brain," the short and simple tale (simple in terms of its core narrative, but certainly not in its execution) of a jaded literary critic who is waiting in line at the bank when the business is invaded by robbers. The story actually has much in common with "An Occurrence at Owl Creek Bridge" in terms of time distortion, and the ending hits even harder than its predecessor. A true classic in every sense of the word.