The web’s funniest stories

I asked Kottke readers to tell me the funniest stories they’d ever read on the web.

Now let me say this: I like to think I have a pretty eclectic sense of humor. I can go high or low, folksy or surreal, G-rated puns or X-rated filth. But some of you… let’s just say a few of you surprised me with some of this. This is some seriously weird shit.

NOTE: To narrow things down, I knocked out anything that didn’t resemble a story. I knocked out videos and focused on text. People who suggested comedy specials on Netflix — I didn’t watch those. I eliminated anything that seemed downright stupid, mean, or just not funny. And I probably dropped a few other links here and there because I closed the tab instead of saving it, or some other reason. This isn’t a scientific survey; this is a blog.

• “So You’ve Decided To Drink More Water,” by Mallory Ortberg. This is pre-Toast Mallory, and it has everything that made her a huge star in the years that followed. (Well, at least a huge star for us.)
• “Dogs Don’t Understand Basic Concepts Like Moving,” by Hyperbole and a Half’s Allie Brosh. It’s true. They don’t.
• “Climb Aboard, Ye Who Seek the Truth!” by Bronwen Dickey. A cruise for conspiracy theorists. Or, if you will, a “Conspira-Sea Cruise.”
• “Downton Abbey With Cats,” by John Hodgman. It’s not a laugh a minute, but this story has a core of melancholy that just makes it deeper and funnier over time.
• “Darling, There’s Something I’ve Been Hiding From You—I’m Jimmy Buffett.” Surprisingly, there was only one entry from The Onion, but it’s a pretty good one.
• “Everything That’s Wrong of Raccoons,” by Mallory Ortberg. This is right at the end of The Toast’s run, and it’s a treat. “I can’t be in trustment of a beast that clambers and waddles both.” Nor should you, Mallory.
• “The Wisdom of Children,” by Simon Rich. I think the best part of this is the adults’ table conversation as imagined by the kids’ table, but opinions may differ.
• “An Oral History of ‘Mad Men’,” by Clickhole. The oral history boom kicked off a terrific run of oral history spoofs by Clickhole. The one for Radiohead’s OK Computer and Michael Jordan’s flu game are also excellent, although after a few, they start to feel kinda samey.
• “TIME FOR SOME STORIES,” by davesecretaryatwork. This is one of those “maybe you had to be there” things, but these set of stories were lovingly carried over from the VivaVinyl.org message board to an Angelfire site that then went down, and finally found a home at somebody’s tilde.club page. Also, two different people nominated it. Who are we to judge what cracked people up in the days before YouTube?
• “An Insider’s Report on the Death of ‘Wilton North’,” by Paul Krassner. This seems like something somebody could have made up, Spinal Tap-style, but in the very early days of the Fox Network, there really was a short-lived late night TV show called The Wilton North Report. Conan O’Brien, Greg Daniels, Alex Sokolow, and other future luminaries wrote for it. I swear to god.
• “Oscar Fug Parties: Lindsay Lohan and Sharon Stone,” by Jessica Morgan. This is now a different kind of funny given the future career arcs of these two actors.
• “Something Close To Madness Case File #24: The Oogieloves In The Big Balloon Adventure,” by Nathan Rabin. A screening of a very strange kids’ movie gets even stranger.
• “The story of Amun-Re, the crappiest god ever,” by Joe Gola. I’ve never played the board game this is based on, but this is an inspired bit of message board fan fiction.
• “The Pitch Meeting for Animaniacs,” by Abbey Fenbert. “EXEC #1: How will kids feel when they watch this show? THE ANIMATOR: Disconcerted. Unmoored. Hyper-stimulated. Amused to the point of terror.” This is so good.
• “In Which I Fix My Girlfriend’s Grandparents’ Wifi And Am Hailed As A Conquering Hero,” by Mike Lacher. Maybe the most McSweeney’s story that ever McSweeneyed.
• “TOTO’S ‘AFRICA’ BY ERNEST HEMINGWAY,” by Anthony Sams. On second thought, maybe the competition for Most-McSweeney’s is stiffer than I thought.
• “My 14-Hour Search for the End of TGI Friday’s Endless Appetizers,” by Caity Weaver. Maybe the most memorable bit of nu-gonzo reporting of this decade. New Journalism had acid trips: we have mozzarella sticks.
• “The Alameda-Weehauken Burrito Tunnel,” by Maciej Ceglowski. This was 2007, but I say if we’re not building hyperloops to send authentic California burritos across the country, then I don’t see the goddamned point.
• “Anecdotal Leads for News Stories Reporting the End of the World,” by Hart Seely. Newly timely! When a friend recently passed this along again, I reached the end and laughed out loud for a full minute like, well, someone who’s facing the end of the world.

There’s still something to be said about the kind of humor that the web makes possible, or at least rewards disproportionately to other kinds of media. There’s definitely more short-form, densely-referential bits that somehow fuse tweeness and gallows humor than you see on television, or even in magazines, which might be their nearest successor. Some savage blend of The New Yorker and underground zines.

It’s a little like what happened to television comedy after The Simpsons showed up. Animation opened up the possibility space for other kinds of comedy, found a way for the weirdest bits of Get Smart and Monty Python to exist in their own separate universe.

The web had a similar effect. You could write anything. You could do anything. No sets to build, no pages that had to be filled. You had endless reflections by comics on podcasts and interviews and their own blogs and social media feeds about what made the funniest things funny. There were all sorts of new media genres you could lampoon, pillory, and steal from on the sly. You had greater collisions than ever before of different people from all over the world and every walk of life who brought their own traditions of humor and storytelling. Amateur and up-and-coming jokesters desperate to connect with friends and strangers. And an audience chained to their desks or stuck on a train or a doctor’s office looking to laugh. That’s just good gumbo.

• best of the web
• comedy