Gameplay: Jokes and Crossword Clues
Plus, solve a special Saturday puzzle.
Gameplay
June 8, 2026

I had been writing and pitching jokes for years before I tried writing crossword clues. I was surprised by how much the two exercises overlapped, like when musicians learn his or her ear translates across different instruments, or when a quarterback realizes he can throw an enemy’s car keys 60 yards away. Different end goals, but a lot of the same muscles.

Both jokes and crossword clues adhere to a two-part structure — the joke has a setup and a punchline, the clue has a prompt and an answer. When executed well, both trigger a sense of discovery in their audiences. In puzzles, this is the feeling solvers describe as the “aha” moment. In the comedy business, it’s called “getting a laugh, baby.” The main difference between the two is who gets to make that connection.

In crosswords, a well-written clue appears opaque, but with enough thinking, erasing and gnashing of teeth, the solver is the one to uncover the answer and be rewarded with a sense of satisfaction. Take this excellent clue from a recent Saturday puzzle by Malaika Handa and Erik Agard: [Fresh Rolls, for example?]. It calls to mind a warm baked good — but it’s a misdirection. The answer is NEW CAR. Here, “Rolls” isn’t a hot bun cooling on a window sill, it’s a Rolls Royce, cooling on an enormous window sill. The puzzle’s constructors may have written the clue, but the solvers ultimately get the joy of discovering the connection on their own.

In comedy, the joke tellers are the ones who make the connection for their audience by revealing the punchline. If the audience members can predict that punchline from the setup, they’re not going to laugh — they saw it coming. This is probably best demonstrated in one-liners, which are usually pure setup-punchline. One of my favorite joke writers, Benny Feldman, excels at these: “I like to surround myself with people who are smarter than me, and then do a big spin attack,” he said during a standup routine. Like a crossword clue, the setup — “I like to surround myself with people who are smarter than me” — is recontextualized with the reveal that he actually has it out for these smarter people. But unlike a clue, the audience members aren’t supposed to find the answer themselves. They want Benny to tell them so they can laugh at the unexpected connection.

An especially clever clue might still get a laugh, but there’s a reason so many puns and dad jokes in the crossword are groaners: They’re designed for the solvers to discover the punchlines themselves. Jokes are stronger when they reveal a hidden connection between disparate ideas, but crossword clues can’t employ that kind of lateral thinking, lest they become obtuse and unfair. (The clue [What to do after surrounding yourself with people who are smarter than you], solving to BIG SPIN ATTACK, would probably not be fair game in the New York Times Crossword.) And of course, a specific clue has a single correct answer — whereas if you asked 10 comedians to write a joke using the same setup, you’ll most likely get 10 different punchlines.

As I construct more crosswords, I’ve learned to appreciate every step of the process, but clue writing is still my favorite. It’s a great feeling to take a word that has appeared in hundreds of crosswords and write a fresh, piping-hot clue for it. Put it in the puzzle; there’s way too much stuff on this window sill.

ARTICLE OF THE WEEK

Three men at a park table setting up pieces on a roll-up chess board.

How Three Chess Friends Battled Demons and Saved Two Lives

A homeless chess hustler, a scholar and an aging recluse found hope in a trashed apartment by Central Park.

By John Leland and Juan Arredondo

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Puzzle of the Week

This week, check out Saturday’s puzzle, by Daniel Bodily. In the Wordplay column, Caitlin Lovinger wrote: “This imposing-looking crossword smashes a record that’s stood for several years, for the most ‘open’ grids in the modern era of New York Times puzzles. This measurement quantifies the number of squares that don’t touch a black block at all, even diagonally, which makes for larger interlocking fields of entries. In this puzzle there are 135 of them; the previous high mark was 132, and there have only been four with more than 130, including today’s puzzle.”

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