The Most Underrated McSweeney’s Humor Pieces of All Time

I love the short, conceptual humor piece: A 300–800 word article of funny writing that exists for no other reason than to be read and cause laughter. McSweeney’s Internet Tendency is, arguably, the best purveyor of the genre. Since the late 1990s, McSweeney’s has published writing for people who appreciate an intellectual and literary slant to their humor, dashed with liberal amounts of silliness — the perfect mix.

Happily, I’ve published several things in McSweeney’s, which is great because I’m such a fan of what they do.

With all due respect to McSweeney’s most popular pieces, today I celebrate not the pieces that went viral but rather the ones that should have.

If I were dictator of the internet, these pieces would get one billion views each. So, here they are: a dozen underrated McSweeney’s pieces that I just love.

1. A Professor’s Opening Lecture for “Intermediate Killer Shark Genre” by Sam O’Brien

“If I catch you teasing one another by placing a perpendicular open palm on your head and humming a certain John Williams score, you will be punched in the face. You will also receive an F.”

The unhinged professor who specializes in shark cinema is pitch-perfect in this hilarious gem by Sam O’Brien. I can also picture this piece as a live, comedic sketch — but then why mess with perfection?

2. Welcome To Hoodwink, The Advertising Agency That Is Not An Advertising Agency by Katie Brinkworth

“We are Hoodwink, a collective of artists, dreamers, poets, storytellers, digital wizards, regular old magic wizards, free-thinkers, freeloaders, disrupters, gambling addicts, misfits, misfit toys that have creepily come to life and refuse to die no matter what we do, and one lone gunman.”

From tumor rats to giant hair piles, each sentence carries delightful little surprises. This piece is one reason Katie Brinkworth is one of my favorite writers on McSweeney’s.

3. Failed Role-Playing Scenarios by Wendy Molyneux

“NURSE: Hi, Ned. Time for your sponge bath. PATIENT: But I’m here for a heart procedure. Why do I need a sponge bath?”

A premise so ingenious it makes me slap my forehead for not thinking of it myself.

4. Henry David Thoreau Can’t Take Much More of These Goddamn Steam Whistles by Coleman Larkin

“I swear, sometimes I’ll hear two steam whistles in the same month. One time I heard three. It’s driving me fucking nuts. I am not a hand-cranked, coil-driven automaton! I am a man!”

Sometimes a piece of satire makes a completely necessary point — grouchy Luddites always complain that the world is changing too fast — and makes it in the most enchanting way: by having Henry David Thoreau rant about steam whistles.

5. “Liquor Before Beer?” The Ultimate Drinking Cheatsheet by Sam Weiner

“Appletinis before Guinness, start a small business.”

Sam Weiner turns the classic “beer before liquor” saying into a crazy list of drinking aphorisms, complete with a mini-narrative about a senator named Jerry. A 100% perfect, wouldn’t-change-a-damn-thing list.

6. My Hobbies by Ellie Kemper

“I know that most people would consider worrying as a necessary evil, but I firmly believe that I must really enjoy it. Why else would I spend so much time doing it?”

A beautiful example of how a short piece can explore a loveably absurd character rather than a super-specific gamey comedic premise.

7. My Lies, Translated by River Clegg

“I actually have very deep preferences about the course of action our group chooses to take this evening, but I’m keeping those preferences private because I fear conflict more than I desire happiness.”

River Clegg spins social anxiety into comedy gold. I think it’s a mark of a smart piece that the narrator here is sympathetic and disarmingly relatable despite being borderline misanthropic.

8. It Was I Who Flipped Over the Risk Board Last Night by Colin Nissan

“Your pigheaded warmongering left me no choice but to violently flip the board while you lay smugly asleep in your bed. I’m surprised the tinkling of game pieces hitting the floor didn’t wake you, but, alas, I imagine you were consumed in despotic dreams of victory.”

The narrator’s frustration with his over-zealous, board-gaming roommate is a masterclass in taking something that basically doesn’t matter in the real world (a game of Risk) and heightening it to hilarity.

9. Here Are All The Ways I Could Have Died Today by Seth Reiss

“During shower, Tiny Man emerges from toilet bowl, hops into shower with me, and says with the friendliest of smiles, “Hey ya, pal, I’m Tiny Man, how are ya?!?” I have a heart attack and die.”

This piece is just what it sounds like: Seth Reiss imagines various ways he could have died.

I’ve read this one out loud to numerous friends, dates, and acquaintances, just to see how they react. You could call it my litmus test for a great (i.e. fucked-up) sense of humor.

10. Five Beautiful Dead Bodies Every Actress Dreams of Playing by Erica Lies

As children, many of our most talented actresses looked doe-eyed at their parents and announced, “When I grow up, I want to play a deranged killer’s victim.”

Like many great humor pieces, this one takes something seemingly niche and offbeat — unknown actresses playing dead bodies in films — and turns it into great satire.

11. A Hypnotized Person Tries To Have Sex With a Chair by Chris Okum

“Feel free to use my shampoo. It’s organic. I stole it.”

I’m not going to describe this gloriously weird monologue by Chris Okum. Just read it. Then read his other pieces. Then contact Chris Okum on my behalf and tell him to write more stuff.

12. I Am A New Meme by Dan Dillabough

“Now I make my home in the decrepit “hotmail”s and “AOL”s where once I feared to tread. My new Carriers all have avatars of bald eagles, or of themselves holding large fish.”

How do you give a voice to an abstract cultural phenomenon like a meme? Dan Dillabough’s piece nails it, feeling both grand in scope but also diving perfectly into the zany subcultures where internet memes do their thing.

Alex Baia contributes to McSweeney’s and runs where he publishes humor, essays, and interviews with amazing writers.

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Humor writer, book junkie, optimist. Words in McSweeney’s, The New Yorker, Slackjaw. I’ll send you some treasure: