Comedy Writing: Easy Wordplay Tips for Thought Provoking Jokes

Wordplay: The Comedian’s Secret Weapon

In the world of comedy, words are more than tools—they’re tricks, puzzles, and keys to surprise. Whether spoken or written, comedy weaves clever wordplay into a mix of wittiness, timing, and relatability.

Many jokes are built on a rhetorical puzzle, a misdirection that resolves tension through surprise, expectation, and sometimes pure coincidence.

If you’ve explored my 9 Psychological Laughter Triggers, you’ll know coincidence is a trigger I get very excited about—I’m a total nerd that way–it’s a powerful tool that taps into shared memories or universal experiences, creating a spark of recognition that can double the laughter.

In fact, I recently discovered that the excitement caused by a connection using the laughter trigger of coincidence is more than just my comedy nerd instinct at work.

Neurologically and hormonally, coincidences engage the brain’s reward centers, activate hormones associated with excitement and bonding, and prompt our minds to search for meaning. That’s why a good coincidence can feel so powerful, memorable, and even life-changing.

The Art of Coincidence

Take Jerry Seinfeld, for example. He masterfully uses coincidence by steering us back to those relatable, “Oh, I’ve done that!” moments. It’s as if he plucks experiences right from our own lives and hands them back to us, but funnier. One of my favorite bits is his “Left” bit:

“I’m left-handed. Left-handed people don’t like that the word ‘left’ is associated with negative things. Two left feet. Left-handed compliment. Bad ideas are always ‘out of left field.’ What are we having for dinner? Leftovers. You go to a party, nobody’s there. ‘Where’d everybody go?’ They left.”

Seinfeld’s clever coincidence here is in showing how a single word—“left”—has layered meanings, all tinged with negativity. But beyond the wordplay, it resonates because we, too, can remember that same feeling of showing up only to find the party is, in fact, over or a dud. I mean do you remember throwing a party and having the fear of nobody showing up?

So, even though Jerry Seinfeld is poking at the multiple implications of the word “left,” he’s also tapping into something much deeper. Which is one reason that even though there’s a large amount of people that don’t find Seinfeld to be “funny,” they still couldn’t help to experience a connection.

The Master of Wordplay: George Carlin

George Carlin took wordplay even further, blending it with language analysis to expose the absurdity of human behavior and language quirks:

“Griddle cakes, pancakes, hotcakes, flapjacks; why are there four names for grilled batter and only one word for love?”

Or:

“Sometimes they say ‘the winds are calm.’ Well, if they’re calm, they’re not really winds, are they?”

And one of my favorites:

“You ever realize on TV you can say you pricked your finger, but you can’t say you fingered your prick.”

This last joke is more than wordplay; it’s chiasmus, a literary device that flips the order of words to create a humorous and surprising twist.

Carlin’s use of chiasmus elevates his joke, not only because it’s unexpected but because the phrase reversal holds a deeper truth. Chiasmus taps into coincidence, too—by flipping words, you reveal an unexpected alignment or connection.

The Power of Chiasmus

Chiasmus itself is a powerful comedic tool, delivering humor through the sheer coincidence of phrase reversal. One classic publishing house rejection letter demonstrates this well:

“Your manuscript is both good and original, but the part that is good is not original, and the part that is original is not good.”

Also the forever famous, “Ask not what your country can do for you, ask what you can do for your country.”

The mirrored structure here doesn’t just draw a smile; it creates a memorable line by flipping expectations.

Chiasmus can help produce a phrase about a comedian’s resilience too: “As a comedian, you have to know how to accept rejection while rejecting acceptance.” Inverting the words introduces coincidence, but it also opens up new ways of thinking about rejection and success.

When used in roast writing, this device can be even more powerful. During one of my Comedy Writing A La Carte courses on roast jokes, we looked at the recent roast of Tom Brady on Netflix, particularly how Rob Gronkowski (a tight end and a regular passing target for Tom Brady—also a known goofball—was a target for roast jokes.

After jotting down a few facts about Gronkowski and Kevin Hart, the host of the roast, a simple, but very effective joke was the result:

“Ron Gronkowski is 6 foot 6. Kevin Hart is 5 foot 5. Backstage when they first met, they stood face-to-face, and… (ACT-OUT: Use your hand to indicate that Hart was at Gronkowski’s belt level).. let’s just say it had a happy ending.”

“Because when you’re nose to nose, your toes are in it; when you’re toes to toes, your nose is in it.”

The joke flows with a chiasmus-like reversal, and it works because the physical contrast between Gronkowski and Hart is both literal and playful.

The Secret to Better Comedy

This simple literary device—chiasmus—is available to anyone.

Digging into chiasmus and other rhetorical techniques doesn’t just make jokes stronger; it trains your brain to think in opposites and recognize coincidences you might otherwise miss. It can be the key to irony, like in this joke about climate change:

“Ever notice that people who don’t believe in climate change—thinking it’s part of Earth’s natural evolution—are the same people who don’t believe in evolution?”

The twist here isn’t just clever; it uncovers truth in an unexpected way, forcing us to laugh at the irony and also provoke thought.

So, next time you’re writing a joke or crafting a routine, try a little wordplay.

Look up chiasmus and try your hand at flipping phrases. You’ll not only discover the power of coincidence but might just find yourself uncovering truths through humor in the process.