River Clegg On Weird Writing Ideas and Insecure Pirates

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Today I’m talking with one of my favorite humorists writing short pieces: River Clegg.

River Clegg is a staff writer for The Opposition with Jordan Klepper. He has written for The Onion, ClickHole, The New Yorker, and McSweeney’s. 


River, you’re a versatile guy. You write for TV, do standup, and write short conceptual humor. What draws you to the short humor piece?

I’m partly into short humor pieces because they were the first type of comedy that I tried writing seriously. That’s probably because I got involved with my campus humor magazine in college rather than joining an improv or sketch group.

But I also like how a short humor piece can create a whole mini-world you can live in for 600 words or so. There’s a lot of creative latitude. A good example is “The Stoner Gods Are Angry,” a McSweeney’s piece by Greg Paulos. It’s one of my favorites. It nails the style of a Homeric epic while really clearly and funnily setting up what I think is a pretty complex situation, and (for me) it’s packed with laughs without getting into a predictable setup-punchline routine.

Has your TV or standup writing affected your short humor writing or vice versa?

I haven’t had a TV writing job for that long, but the schedule has definitely limited the time I can spend on short humor writing. But in general I’d guess that doing stand-up and writing for places like The Onion have made my short humor pieces more economical and joke-heavy.

When you’re writing a piece that’s 600-800 words, there’s a lot of opportunity to drag your feet. But when I was writing Onion headlines, I tried to give them a limit of ten or twelve words, so I had to get to the laugh quickly. I’ve tried to apply that same idea to my short pieces.

One of the challenges of the short piece, to me, is quickly finding a rhythm. Sometimes that means every line is funny, sometimes not.

You have this awesome piece, “I’m A Disruptor,” that’s packed with absurdities and every line is a joke. Contrast that with your McSweeney’s piece “The First Black Friday,” which feels more akin to the Stoner Gods piece; not every line is a laugh but the piece as a whole takes you on a journey. Is that a difference you’ve thought about?

Thanks so much. “Disruptor” was one I worked on with my friend Evan Waite, who has a great ear for weird, absurd-sounding jokes. I think the key is making the jokes feel organic to the piece, which sometimes means I try to learn more about the language I’m poking fun at. So for “Disruptor,” we tried to capture that manic, over-the-top confidence and energy of people who talk about themselves as disruptors. Similarly, for “Black Friday,” I did some (very light) research into the writing style of early New England colonizers, just to try to absorb some of it. Obviously, you don’t want to get so attached to historical veracity that it gets in the way of a funny style, but doing that kind of legwork can help you develop the voice that you write the piece in, and that will inform how the jokes come out. Plus, hopefully, the style is funny enough that the reader laughs even in between the jokes.

What do contemporary writers do that annoys you?

I get annoyed by grammatical superstitions, like “never begin a sentence with ‘and’ or ‘but,'” “never split an infinitive,” that kind of thing. I got the term “superstition” for these myths from Bryan A. Garner’s “A Dictionary of Modern American Usage,” and he’s got a whole collection of them in there. It’s frustrating.

I also get annoyed with pieces of writing that are longer than they need to be, and when the writer needlessly injects themselves into the argument they’re trying to make.

What’s something you’ve done that unexpectedly made you a better writer?

Anything you do (or read) that’s unusual or weird or niche will make you a better writer, I think. Basically, the more you know about, the more you can write and joke about. I bought a reissue of a grocer’s handbook from the 1800s a year or two ago, and it’s really interesting to flip through. You basically learn how grocers did business back then, what they stocked, how they catalogued it all, etc. And it introduces interesting vocabulary.

Anytime I do that kind of thing, where I get to learn something niche or archaic, I think it helps my writing. Another book that I flipped through in college and found helpful is “Style Toward Clarity and Grace,” by Joseph M. Williams. It’s just a writing guide, not for comedy, but I think it made my writing much better and clearer. I remember it being great and would recommend it for any writer.

I’ve found the same. In his writing book, Steven King said that if you don’t have the time to read, you don’t have the tools to write. As a writer, I want to read as much as possible, to feed myself.

Cormac McCarthy is one of my favorite people to read, even though I’m not writing stuff that’s at all like his work. His books expose you to a totally different world, and I think there’s a lot that’s appealingly simple and primal about it. I’m reading “The Crossing” now. It’s about a boy trying to take a wolf back over the border into Mexico. It’s beautiful and simple. It’s like a fable.

Any (other) cases of reading or experiencing something offbeat, and it lead to a humor piece idea? I like that possibility.

I wrote a piece called “Honest Museum Audio Tour,” and I got the idea on a vacation where I went to a ton of museums. I started thinking about how weird museums are, and all the strange little thoughts and interactions that go on in them. I wrote a piece called “Rant” about trying to use Facebook to cope with Donald Trump’s victory, which was just a parody of the poem “Howl.” But ideas can come from anywhere. Music or a play or a funny interaction you have. I think the key is just not to let those little ideas escape. Write them down.

I’ve noticed in your writing that sometimes you’ll hit contemporary stuff, say, marketing or internet culture, and sometimes you’ll go for something more left-field, like “The Lost Journal of Blackbeard,” or that William Bradford Black Friday piece. Where’d those ideas two come from?

“Blackbeard” and “Black Friday” just came from weird ideas I had that I wanted to type up to see where they went. I like offbeat stuff like that. The idea that Blackbeard was secretly an insecure mess was just super funny to me. Also, I can personally relate to that kind of insecurity and anxiety. “Black Friday” was similarly weird, but it also made fun of advertising culture, which I keep coming back to. Ad culture and internet culture are both big for me because I think they both can be toxic and addictive, so I think they’re worthwhile targets. They’re also both so pervasive that they’re basically a shared experience for us all, and anytime you can write about something that you and your readers are both experiencing, I think that’s good.


Read humor by River Clegg on The New Yorker and McSweeney’s, and follow him on Twitter

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Written by

Alex Baia is a humor writer and contributor to McSweeney’s and Slackjaw. He lives in Austin, TX.