The Year’s Best Humor Writing

Save the occasional illustration, picture, or creative departure from form, print and web humorists are charged with making us laugh without the benefit of many bells and whistles. From original conceits to clever and consistent executions, everything has to be on the page (or screen). One would think that because humor in print has existed as long as the written word itself (probably! That seems true!) and even before — surely oral tradition must have included some knee slappers — every conceivable topic would have been explored by now and the well would be long dry. 2010 has proven that humorists’ fodder won’t soon be in short supply.

Below are a some of my (and several other people’s, including Jack Stuef (Wonkette, The Onion), Summer Block Kumar (McSweeney’s, The Rumpus), Todd Hanson — sort of (The Onion), stand up comedian Dan Telfer, comedian Eliot Glazer (Urlesque, My Parents Were Awesome), Ted Travelstead (Vanity Fair, Sex: Our Bodies, Our Junk), and Mike Sacks (And Here’s The Kicker, Sex: Our Bodies, Our Junk) favorite humor pieces of the year.

  • A Great Opportunity!” by Kirstina Loew - McSweeney’s — Hardly distinguishable from some of the more outrageous ads actually posted on Craigslist (sans the typos and chance you’ll be assaulted), “A Great Opportunity!” nails everything that’s ridiculous about the site’s jobs section. Expectations are too high, pay is too low — and in our current economic climate — competition is too steep, so non-opportunities like this one seem promising. Even potential employers in search of a “Rabbi Versed in DARK TALMUDIC ARTS to create GOLEM” (No pay; as everyone knows, one has to work one’s way up the golem-conjuring ladder) or, at a tempting $12/hour, someone “to listen to conspiracy theories and other outer space visitor stories” (college degree preferred) — both real posts — were probably flooded with applicants.
  • Orations of a Pre-Post-Colonial Oompa Loompa To His Revolutionary Brothers in Arms” by Marissa Medansky - McSweeney’s — I always thought the Oompa Loompas got a raw deal and probably should have unionized — even as Willy Wonka positioned himself as their great liberator. But how long was he really going to hang that over their heads? I’m getting carried away. This piece comforted me in the fact that there are other people as concerned with Oompa Loompian politics as I am. Up with the adorable, orange-faced proletariat!
  • Google Docs Breaks Up With You” by Jeramy Kraatz - McSweeney’s — If the machines ever DO rise, the revolution will begin with Google. Jeramy Kraatz imagines Google as Skynet — or worse HAL — in this piece about a Google Docs user who has no idea the program is sentient. Teddy Waynes’ 2009 McSweeney’s piece, “Yahoo’s MAILER-DAEMON Automated Reply for Failed E-mail Delivery Is Getting a Little Too Intimate” and Dan Bergstein’s “Search and Annoy” (Grin & Tonic) take this technology-based paranoia to its natural end, with Google thinking in the latter “Sometimes I wonder what your kisses would feel like.” Creeeepy!
  • Videogum’s Top Chef Recaps — I’ve been reading and commenting on Videogum since late 2008 and nearly everything on the site is comedy gold, but earlier this year, my mother sent me an email about hilarious Top Chef recaps she’d found — and the link was to Videogum. The looming threat of my mom’s presence on the site became an on-going gag in the comments for a week or so and she really got a kick out of it. For that reason alone, the site’s Top Chef recaps are among my favorite humor writing of 2010. Gabe Delahaye — The Great Equalizer. And considering that he has to be funny every day, several times a day, I’d say that Gabe’s writing deserves a place among pieces from The Onion and Shouts and Murmurs.
  • Udder Madness” by Woody Allen - Shouts & Murmurs — If I’m making a list of my favorite comedy ANYTHING, Woody Allen’s probably going to be on it — and not in an everyone-loves-Woody-Allen way. All hype aside, “Udder Madness” is hilarious. Though the story’s most odious character — and object of our speaker’s (a cow!) ire — is clearly some harshly envisioned incarnation of Allen himself, learning in the piece’s introduction that “20 people a year are killed by cows in the United States… . In 16 cases, ‘the animal was deemed to have purposefully struck the victim’” makes the consummation of the story’s inevitable tragedy more bearable. Because he’s described as a “wormy little cipher”, “insufferable little nodnik”, “fatuous little suppository”, “natting little carbuncle”, and “stricken little measle”, by the story’s end we’re rooting for the cow to destroy this fellow. When our narrator ascends a staircase to enact his murderous rage, I, a cultured person of the world who discovered while watching a recent episode of Sesame Street that cows can’t go down stairs (something about their knees), figured that’s how Allen’s story would end — with the cow caught red handed. But Woody veers away from expectation and the story ends as it should — an ending I won’t reveal because everyone should read this piece.
  • Remembering Justice Stevens” by Ian Frazier - Shouts & Murmurs — I wasn’t able to verify any details of this story. Was Ian Frazier ever really a Supreme Court clerk? Seems plausible. Did Justice Stevens ever really get attacked by bees? Not out of the realm of possibility. That’s where the feasibility ends. This maybe-true story is exactly how a raven’s like a writing desk — in that I can’t make heads or tails of it and it’s completely absurd. And very funny.
  • Et Tu, Brooklyn” by Allison Silverman - Shouts & Murmurs — I don’t live in Brooklyn, but the culture Allison Silverman describes here exists everywhere — dickheads in London, in San Francisco’s Haight-Ashbury neighborhood and in Portlandia. Here in Chicago, it’s called Wicker Park. Each place is a sanctuary for aging h******s, clinging to a lifestyle that with every passing year becomes more difficult to maintain. Upon hearing of a close friend’s pregnancy, Silverman’s narrator is heartbroken: “We were supposed to make the world safe for babies by speaking truth to power… Pretty soon, she’d only care about stupid stuff.” Our speaker is the last woman in a world of her own creation; Allison Silverman captures the loneliness and betrayal of being marooned in Brooklyn as her friends forsake h******dom for more mainstream existences beautifully and hilariously.
  • Wit of Winston” by Gabe Durham - Yankee Pot Roast — Was Winston Churchill a cad? If his characterization in this piece is to be believed, he wasn’t the just orator we’ve been made to believe he was. Of course, this is all made up — and reminds me of my favorite SNL impersonations, the ones that have little to do with the people they lampoon. There’s comedy in accuracy and exaggeration, but absurdity is so much more fun — The Onion’s notoriously ridiculous take on Joe Biden for example.
  • And Now A Few Minutes With Andy Rooney’s Homo Erectus Ancestor” by Andy F. Bryan - The Morning News — Read this piece in Andy Rooney’s voice and try not to laugh. I Triple Dog Dare You! You can hear Rooney’s warm, but wooden inflection and the strange way he parses his sentences in Bryan’s style. In season one of Mad Men, Roger Sterling bets that “there were people in the Bible walking around complaining about kids today”. Andy Rooney’s progenitors may just have been among those people.
  • Scared Straight” by Simon Rich - Barnes & Noble Review’s Grin & Tonic — Before people took to XtraNormal’s text-to-video service to parody the barriers to entry in their chosen professions, Simon Rich was crushing dreams in his humorous piece “Scared Straight”. Want to marry your high school sweetheart? Want to major in philosophy? Want to be a humorist? Bad Ideas! All!
  • Out of Print” by Teddy Wayne - Barnes & Noble Review’s Grin & Tonic — You know those departures from form I mentioned in the intro? They’re employed here to great effect. Wayne’s meta handling of the demise of newspapers (ironically published online!) toys with convention to illustrate just how spendthrift print news has become. Missing paragraph indents, punctuation, and vowels — because they’re outside of the newspaper’s budget — are not just syntactical gymnastics for their own sake, but work in service of the bit.
  • Dear Mr. Thomas Pynchon” by Mike Sacks & Scott Rothman - Barnes & Noble Review’s Grin & Tonic — Whenever I have to speak to or email someone I admire, I fear I come off like delusional, megalomaniacal aspiring author Rhon (silent “h”) Penny. The piece above, by Mike Sacks (my favorite humorist at the moment) and Scott Rothman, is one of many in the Rhon Penny series — a series in which he writes to famous authors begging for their endorsements and collaboration — in this case, a book jacket blurb. Rhon is part Kenny Powers, part Mr. Collins from Pride & Prejudice, (“There is a mixture of servility and self-importance in his letter, which promises well.”) — a man in whom a lack of self-awareness is bred with the cloying flattery of a shameless sycophant — all hilarity and cringe-worthy second-hand embarrassment.
  • Domestic Conflict, Explained by Stock Photos” by Kevin Nguyen - The Bygone Bureau — Stock photos are chock full of unintentional humor. And they can be oddly specific. I was writing a piece about effective thrift store shopping for a website targeted at black women and needed a few pictures of “happy black women shopping” and these are what I found. That photos of any situation, condition, or emotion are available at the click of a button is strange enough — but the models in the photos are clearly phoning it in. Any chance to mock this service is welcome.
  • Funny Women #1: The New Rumpus Humor Column: I Am Sorry That I Didn’t Write A Comedy Piece” by Wendy Molyneux - The Rumpus’s Funny Women Column — This conceit — Women Aren’t Funny, But I’m A Funny Woman! — has been done before, but because this was written in response to Christopher Hitchens’ puzzling Vanity Fair Piece “Why Women Aren’t Funny” and was the inaugural entry in The Rumpus’ amazing Funny Women column, I’ve got to include this subversive piece by the talented Wendy Molyneux. Even without the context, this is a great read.
  • Finally! A Job That Requires My Skill Set” by Maribeth Mooney — This and “The Only Thing That Can Stop This Asteroid is Your Liberal Arts Degree” by Michael Lecher in McSweeney’s will probably make you question your life choices. Your degree won’t save the world — much less get you a job or allow you to communicate normally with everyday folk, and just in case you’ve forgotten, servicey humorists remind you by writing about it CONSTANTLY. See Eliot Nelson’s “A Robbery of Three Liberal Arts Graduates: A Police Report” for more abuse.
  • Whim Quarterly’s Conversation Pieces by Matt Passet — What do you know about Michaelangelo (either one!)? Or Frank Capra? Probably no more than Matt Passett, who imagines conversations between people about whom he possesses only the most common knowledge. The premise is so simple and so funny that when I read the series’ first incarnation in McSweeney’s a few years ago, I wished I’d thought of it myself.
  • Trouble” by Summer Block - The Nervous Breakdown — Maybe it’s because of my disruptive youthful rebellion, but I go out of my way not to stir the pot these days. I’m all gratitude and contrition — to a fault. Summer Block Kumar seems to be the same way, but she skipped a few of the more difficult steps. Her aversion to conflict arose innately and gets her into more trouble than the trouble she avoids — more specifically, it gets her in an alley dumpster behind a nail salon. Read it. It’s great.
  • Bob Powers’ Blog - Girls Are Pretty — I can’t pick one piece from Bob Powers’ blog. Every day’s a holiday. Every piece is an origin story. If you’re a sucker for hilarious creation myths (which I guess is a thing) you’ll bookmark this blog and give yourself a reason to celebrate more often than is healthy. Because of Girls Are Pretty, I’ve converted from a believer of Festivus (for the rest of us) to an observer of “You Stink of Tears Day!
  • African-American Community Calls for New Black Nerd Archetype” and “New Study Finds Blacks More Likely” – The Onion — I don’t know if they’re purposefully written this way, months apart, but pieces in The Onion seem to appeal to me in pairs. See also: “Local Manhattan Boy Makes Good” and “Hometown Boy Makes Good Enough”. About the links above: we’ve got Donald Glover — and it’s true: we are far more likely.
  • * * *

    (Your Wildest Dreams Within Reason, And Here’s The Kicker, Sex: Our Bodies, Our Junk, Vanity Fair)

    I liked a lot of humor pieces this year, but if I had to narrow down my favorites, I’d say that Teddy Wayne’s book “Kaptoil” ranks near the top. Teddy’s a friend and a great writer, and I really loved the main character of Karim. Check it out HERE.

    Another friend, Yoni Brenner, is a very funny writer, and he’s been contributing to the New Yorker. Loved this piece. Captures government-speak very well HERE.

    Todd Levin, who writes for Conan, wrote a very interesting piece for GQ on what happened to The Tonight Show.

    This site is great, day after day. Bob Powers is always top-notch: .

    And I co-wrote a book with friends that I liked a lot (not necessarily my sections, but what they wrote). This came out last summer: Sex: Our Bodies, Our Junk.

    (Vanity Fair, Sex: Our Bodies, Our Junk)

    I love this piece by Bob Powers. It’s one of many written by him this year that are just fantastic. I’m kind of always in awe of how prolific a writer he is and how consistently funny his pieces are.

    Sam Sifton isn’t afraid to be funny when he writes about food. I think that’s because he must realize that the majority of good meals are infused with laughter. This was one of my favorites by him this year.

    Erin Whitehead is frank, forthright, and absurdly funny. She’s not afraid to sacrifice her dignity to make us all feel better about ourselves.

    I laugh a lot reading this. You realize very quickly why Stephanie Gutierrez and Adam Carl mustn’t be together, and, more importantly, why they certainly should never be apart.


    I had no interest in the Real Housewives franchise until I started reading Richard Lawson’s recaps of the NYC Housewives on Gawker, which are nothing less than epic. His imagined narrative of etiquette-obsessed Countless LuAnn as a gambling, nomadic cowgirl-hooker is enough to get me to read every last word of his recaps, no less make me an obsessive fan of the show, always knowing that waiting for me the following afternoon will be Richard’s beautiful capture of the mind-blowing nuances that we all think we’re the only ones to notice.

    As a comedian, I’m completely fascinated by one-note comics of the 80’s, so I somehow wrangled an interview with prop comic Gallagher a couple of years ago for The Apiary, where the dude turned out to be so nuts, I literally couldn’t understand what he was talking about, and that included a “hotel in the round.” David Wolinsky’s profile of him for The AV Club at the latter end of 2009 proved that Gallagher has truly gone off the rails, no less becoming a bigoted, delusional instigator in the process.

    I tried to avoid the whole Insane Clown Posse phenomenon that bled from the blogosphere to Saturday Night Live, but Brian Raftery’s profile for Wired of the Juggalo “culture” filled me in on everything (including the fact that, whaddyaknow, Gallagher shows up to perform sometimes).

    Rex Reed’s bitchy review of Sex And The City 2 (which, as a gay man, I was “supposed” to see, but spent my money on tacos instead) for The New York Observer slaughtered me, which says a lot, considering movie critics had the times of their lives to lampoon something so fucking awful.

    (Wonkette, The Onion)

    Houseguest Just Going To Lie There Until Rest Of House Wakes Up,” The Onion, 3/4/10

    Though I’ve written some Onion pieces this year I’m really proud of, mostly ones concerning the athletic prowess of horses and fish, it’s hard to say they’re among the publication’s very best. And while the dick-joke epic “World’s Power Brokers Hold Annual Summit Where They Show Each Other Their Penises” comes close, for me “Houseguest Just Going To Lie There Until Rest Of House Wakes Up” was the top article this year. In The Onion’s decades-long observation of “area man,” rarely have the details of the white-schmo plight been so pitch-perfect or the contrast of the news-story frame illuminated its banality so successfully.

    Your New College Graduate: A Parents’ Guide,” Simon Rich, The New Yorker, 5/24/10

    As a member of the class of 2010 who moved back in with his parents after graduating with no prospects of a real job, I probably would have been offended if someone sent me this. And then I would have wallowed in comedy-writer jealousy, yet again, of this twenty-something who is somehow more successful than me. Instead, I appreciate its brilliance. Simon Rich is known for his more absurd stuff, and this premise, uncharacteristically, is not actually all that original; in fact, it could have been conceived by Shouts & Murmurs’ usual stable of older writers. But while their versions of the same piece would have likely been filled with trite observations and confused, anachronistic criticisms of grunge kids, Rich’s piece is a smart, funny, and accurate distillation of his generation.

    Eyewitness News With Tom Denardo and Cheryl Clayburn,” Seth Reiss, McSweeney’s Internet Tendency, 9/23/10

    Like any complete hack (and probable terrorist), The Onion’s Seth Reiss relies heavily on repetition in his “humor works.” And, every once in a while, it accidentally works. I’m insanely jealous of this piece for its amazing rhythm, and my only consolation is that he was not paid a cent for writing this. Ha ha, Seth.

    (McSweeney’s, The Rumpus)

    Anaïs Nin’s Hot Cross Buns” by Rebecca Coffey from The Rumpus’ Funny Women column. I admit it, I can never get enough literary humor, and this is one of my favorites of the year: smart, hilarious, and slightly sexy in a daffy way.

    Damaris Dice, Stand-In Advice Columnist for Latina Magazine” by Jennine Capo Crucet from The Rumpus’s Funny Women column. I loved this when I first read it; then I heard her read it live and it was even better. Crucet is one of a few writers who is just as good being funny as being serious - or both.

    12 Differences Between Caddyshack and Reality, as Dictated by Depression” by Nathan Pensky in The Nervous Breakdown.

    One of my favorite pieces on The Nervous Breakdown from a writer I just discovered this year; I’ll definitely be following all of his stuff in the future.

    The Shopping Lists of Rudy Shlomka” by J. Ryan Stradal in Facsimile.

    Another piece I first loved when I heard it live, but it reads just as well on the page, from one of my favorite humorists. Stradal has a distinctive, charming persona: sarcastic but not cynical, and surprisingly generous for a satirist.

    My favorite piece of mine this year is Baby’s Touch n’ Feel Guide to Russian Literature from McSweeneys.

    Conan’s “People of Earth” letter: Conan has said himself not to pity him or make him a martyr, but to see a creative mind actually draw a line in the dirt on this scale? My brain exploded with optimism, and I laughed with awe.

    Rob Delaney’s “Comedy” for Vice Magazine:

    If you want short, annihilating one-liner humor, follow Rob Delaney on Twitter. If you want one of the most important perspectives on depression and its relation to comedy, read this essay, where Rob still take time to make hyperbolic threats and insults towards the reader to keep things, well, almost light.

    Todd Hanson

    (The Onion)

    There were no funny things in 2010, unfortunately. None at all. No wait, there was that one movie with the guy. The one with high-energy hi-jinx. Or was that in 2009? I can’t remember anymore. Anyway, that was it. Nothing else funny happened that I can recall. It was a weird year that way. Usually lots of funny things happen all the time (hell, every DAY… am I right?) but for some reason not in 2010. Why do you ask?

    Is Becca O’Neal a Chicago-based freelance writer? Because her mom is kind of worried.

    The Year’s Best Humor Writing