Famous Crossword Puzzles and the Stories Behind Them

A crossword is supposed to be a quiet thing — a grid, a pencil, a cup of coffee. But every so often a single puzzle has slipped into history for reasons no constructor could have planned: a wartime security scare, an election-night trick that made readers gasp, a grid that quietly invented an entire pastime. These are some of the most famous crossword puzzles ever published, and the stories behind them are far stranger than the grids let on. Once you've read them, you'll never look at an innocent puzzle the same way — so go on and play a crossword afterward with fresh appreciation.

The D-Day crossword panic of 1944

This is the most famous crossword story of all, and it really happened. In the weeks leading up to the D-Day landings in 1944, the crossword in Britain's Daily Telegraph began coughing up words that made military intelligence break out in a cold sweat.

One puzzle's answer was UTAH. Another, OMAHA — the code names for two of the invasion beaches. Then came OVERLORD (the code name for the entire invasion), MULBERRY (the secret floating harbours being built for the landings), and NEPTUNE (the naval assault phase). Five top-secret D-Day code words, all surfacing in the same newspaper crossword in the run-up to the most secret operation of the war.

MI5, Britain's security service, was alarmed enough to investigate. They tracked down the puzzle's compiler, a mild-mannered schoolmaster named Leonard Dawe, and questioned him. Was the crossword a channel for leaking secrets to the enemy? Dawe could only insist it was a coincidence, and he was eventually let go.

The likeliest explanation only emerged decades later. One of Dawe's former pupils came forward to say that the headmaster sometimes let students fill blank grids with words, which he would then write clues for. The boys' school sat near camps full of American and Canadian troops, and the soldiers, with astonishing carelessness, tossed these code words around. The students picked them up and innocently dropped them into the crosswords. A genuine security nightmare, caused by nothing more sinister than schoolboys with good ears.

The 1996 puzzle with two correct answers

On the morning of the 1996 US presidential election — Bill Clinton against Bob Dole — solvers of the New York Times crossword hit a clue that seemed impossible to get right: "Lead story in tomorrow's newspaper."

The answer ran seven-plus letters across the middle of the grid. Some solvers confidently wrote CLINTON ELECTED. Others, just as confidently, wrote BOB DOLE ELECTED. And here's the astonishing part: both were correct. Constructor Jeremiah Farrell had engineered the puzzle so that every Down answer crossing those squares was clued to work either way. Where one solver read a letter as part of CLINTON, another read it as part of BOB DOLE, and the crossing clues had been written so both readings produced valid words.

It didn't matter who won the election — the crossword had already predicted the result perfectly, twice. Times crossword editor Will Shortz has called it his all-time favourite puzzle. On the day, plenty of readers phoned in convinced they'd caught a glaring error, never realising they'd stumbled into one of the cleverest tricks ever built into a grid. Solvers nicknamed it the "Schrödinger puzzle," after the famous cat that's alive and dead at once.

The grid that started it all

No list of famous crosswords is complete without the very first one. On 21 December 1913, a journalist named Arthur Wynne filled some space in the New York World with a diamond-shaped grid he called a "Word-Cross." It looked a little different from a modern puzzle — no black squares, an unusual shape — but it had the numbered grid and interlocking across-and-down answers that define every crossword since.

Wynne could not possibly have known he'd invented a global obsession. Within a decade the crossword was a full-blown craze, and within thirty years even the newspaper that had sneered at it as "sinful" was running its own. The full story of that journey is in our history of the crossword.

When crosswords became a culture

Famous crosswords aren't only about individual puzzles — the pastime itself has had its star turns. The American Crossword Puzzle Tournament, founded by Will Shortz in 1978, turns solving into a competitive sport, with hundreds of solvers racing through the same grids against the clock. In 2006 the documentary Wordplay followed that tournament and its celebrity fans, and turned a quiet hobby into a genuine pop-culture moment. The crossword had come a long way from a space-filler in the Sunday "Fun" section.

What ties these stories together is how much life a simple grid can hold — secrets, jokes, history, obsession. The next time you sit down with one, remember it belongs to a tradition full of panic, genius, and the occasional impossible clue with two right answers. Play a crossword now, or learn the wordplay behind the trickiest grids in our cryptic crossword guide.

Frequently asked questions

What was the D-Day crossword panic?

In the weeks before the 1944 D-Day landings, the Daily Telegraph crossword contained several top-secret invasion code words — UTAH, OMAHA, OVERLORD, MULBERRY and NEPTUNE. British intelligence (MI5) investigated the compiler, schoolmaster Leonard Dawe, fearing a leak. The likely explanation, revealed decades later, was that his students had overheard the words from nearby American and Canadian troops and innocently used them to fill in practice grids.

Which crossword had two correct answers?

The New York Times crossword published on US Election Day in 1996, constructed by Jeremiah Farrell. The clue "Lead story in tomorrow's newspaper" could be answered CLINTON ELECTED or BOB DOLE ELECTED, because every crossing Down clue was written to work with either letter. Both answers were completely valid, so the puzzle correctly "predicted" the election no matter who won.

What was the first crossword puzzle?

The first crossword was published on 21 December 1913 in the New York World, created by journalist Arthur Wynne. He called it a "Word-Cross" and gave it a diamond shape with no internal black squares. It introduced the numbered grid and interlocking across-and-down clues that define crosswords to this day.