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The web’s funniest stories

posted by Tim Carmody   Apr 20, 2017

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.

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.