The Written Pun and Other Travesties


Pun’s are often better spoken, at least the ones where the focus of the pun is a word spelled two ways or pronounced strangely. That and a sense of comedic timing is more challenging in writing than in speaking. The topic came to mind because a pun/joke came to me as I was waking up, half dreaming, half aware. The sleepy version was…

-Who is the most popular person in a haunted tavern?

-The one buying all the boos.

It seemed terribly clever to me in my muddled state, and it’s not a terrible pun. It kicked off my awakening process which tends to be long and tortured. I kicked the wording around in my head and decided I liked this one better.

-Which is the most popular spirit in a haunted tavern?

-The one with the most boos.

Now both the question and the answer become puns with interchangeable meanings, two puns in one joke! I did a quick google search to see if I had only re-invented the wheel and to my surprise, this form of the joke wasn’t to be found. The closest was “Why did the ghost go to the bar? To buy some boos.” Close to my original, but not quite up to the challenge of my refinement. Assured of my own cleverness, I posted my joke on Facebook. Writing it, I wondered: “What is funnier ‘the most boos’, or ‘the most booze’?

My thinking was that the less obvious meaning, the one with less context in the rest of the text should be the one you use to elicit the most surprise. When you say it that doesn’t matter, and part of the joy of a pun is the other person “figuring it out”. That slightly delayed understanding is part of the comedic effect of a pun so writing it in a way that enhances that is the direction to go. Mind you many puns don’t have double spellings, only double meanings and those are just as effective in writing as if spoken.

I did a little research on writing puns and didn’t find an opinion on this specific question. I did find a great article about writing puns that are detailed, insightful, and contains many excellent examples of the form. You can find it here. I really enjoy analyzing humor and refining jokes. It is said the fastest way to rob humor of its power is to analyze it or explain it, but I think that crafting jokes is as fine an art as telling them.

Let me close with my favorite pun, hailed as the greatest pun ever told (for reasons you will discover). And don’t worry, pointless explainers and analysis will follow. 🙂  I told you there would be Travesties here!

I love puns. I always have. I likely picked up a fondness for them from my father, Goodwin Trent, who has at least as great a love for them. In 1998 the New York times held a contest to crown the “Greatest pun of all time.” Contestants from all over the English-speaking world were invited to send their best puns, as many as they liked, and their panel of experts would pick just one as the pinnacle of the artform.

While I was intimidated by the scope of the competition, I was determined to show my love for the artform and submit my own original entries. It was tough. I had to not only come up with a pun that would be incredibly clever, but that would be largely original, something no one else would have thought of in all the years of pun-craft. Puns have been found in Egyptian hieroglyphics so we are talking about a long history of wordplay.

Undaunted I got busy. Armed with my laptop, a good supply of liquid inspiration, and a google window to check for originality I set about my work. Every evening for two weeks I worked and re-worked puns. Not shockingly, many had already been invented and published by others online. Slowly but surely I came up with a long list of puns that I was unable to find close matches for. In fact, as time went on I found I had a pretty long list of candidates.

It took those and started to work them over, honing each and every word so it was perfect. I ended up throwing out quite a few groaners in the process. Finally, as the deadline approached I had winnowed my list of submissions down to ten of the most well-crafted puns I could possibly invent. My heart beating, I put each one in an envelope and mailed them to the Times.

I waited with baited breath for the next 8 weeks as puns all over the world were read and judged by men and women who loved the art as much as I. Would I win? Would they even laugh? The tension was honestly brutal while I waited for the big day. I so hoped one of my puns would win fame and glory forever, but when the announcement came, no pun in ten did.


Yep, it’s a pun, it’s a shaggy dog, and the punchline is a meta-pun reference full of irony. So lovely, so painful, just perfect!

I did not create this pun, I heard it “somewhere” probably on a TV show or the like. I’m pretty sure it’s an old one that has made the rounds well before my time. This telling of it is my own. That’s the great thing about a shaggy dog story. Generally, the only thing that matters is the context and the punchline so the rest of it is up to you to embellish. The key to a Shaggy Dog is engaging the listener/reader in the story. You want them involved and interested, unsure of where the story is going, and utterly unprepared for the lameness or irrelevance of the ending to the drama of the story.

I decided it was essential that the story be a personal one. That way I could introduce it as an anecdote related to puns rather than as a pun. That way you enhance the engagement and maximize surprise. They may wonder if this really happened or what, especially if the telling is smooth and rehearsed, but that too helps immersion. The more they are thinking and analyzing, the bigger and more brutal the reveal when you get to the ending. I introduce it here as a pun up front, but in real life, I’d transition it as a story. “Did I ever tell you about the time I tried to make the greatest pun ever written?” To enhance the illusion I mention my father by name, who it is true loves puns very much.

In the version I first heard, the contest was unspecific: “there was once a contest”. I decided that as a personal story, it needed hard details to make it feel more real. I decided it would be a New York Times contest since they are an international newspaper and the notion is plausible. I named a date 1996 that is a while back, but feels somewhat contemporary and plausible given my age yet is long enough ago folks likely would not remember if it happened or not.

The essential elements of this one are: There is a pun contest, ten entries were made, and the punchline, no pun in ten did. Everything else is up to you to try and get some engagement and interest in the story to make pulling the rug out more fun. It doesn’t have to be a shaggy dog. If you want pure pun (my grammar checker wants to know if I meant to type “fun” here), then you can tell it in three sentences. I like the longer form better. I will note it’s important you name the number of entries, ten, fairly close to the punchline so the double meaning is fresh in mind when it hits.

Finally, I’ll note that I didn’t do what I said I should do when I wrote the punchline. My instincts told me in this pun it was better to write it in the way that makes sense in the story context, and let the second, subversive meaning be the one that dawns on the reader. Really, it probably works either way thus defeating the entire point of this exercise except to tell you some puns. Sorry about that. 🙂


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