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Data Study: The Top 10 Hardest Crossword Clues of All Time

January 14, 2026

Crossword puzzles rely on a mix of trivia, wordplay, and fill-in-the-blanks. But some clues are designed to be purely structural—vague definitions that fit hundreds of different words. We analyzed our database of 12 million clues to isolate the most frustratingly ambiguous prompts in history.

📊 The Data: Ambiguity Index

#1 "Girl's name" 310 vars
#2 "END OF QUOTE" 215 vars
#3 "THEME OF THIS PUZZLE" 202 vars
#4 "End of the quote" 148 vars
#5 "Man's name." 147 vars
#6 "START OF A RIDDLE" 143 vars
#7 "Riddle, part 2" 127 vars
#8 "End of the riddle" 124 vars
#9 "Man's nickname" 124 vars
#10 "RIDDLE, PART 3" 122 vars

Data source: GrabThisWord Internal Database (2024)

Deep Dive: The "Impossible" Clues

#1

"Girl's name"

Ambiguity Score

310 possible answers

Common Answers

EULA, NADINE, REBA, KARLA, SONIA, ...

This clue is notoriously vague. Depending on the puzzle theme or length, it fits hundreds of words. See all solutions →

#2

"END OF QUOTE"

Ambiguity Score

215 possible answers

Common Answers

MADEITWEVEHADIT, ANDTELLTHEFACTS, FOXHOLES, YOUDSAID, ANDTHENNOTPLAYANYMORE, ...

This clue is notoriously vague. Depending on the puzzle theme or length, it fits hundreds of words. See all solutions →

#3

"THEME OF THIS PUZZLE"

Ambiguity Score

202 possible answers

Common Answers

THINGSYOUSTRIKE, BROOKLYNDODGERS, JERRYLEWISFILMS, ELVISSIGHTINGS, LOCKERROOMTALK, ...

This clue is notoriously vague. Depending on the puzzle theme or length, it fits hundreds of words. See all solutions →

#4

"End of the quote"

Ambiguity Score

148 possible answers

Common Answers

THESUNSHINES, MYSELF, ANDYOUREINTOJAZZ, MUSIC, WHATTODO, ...

This clue is notoriously vague. Depending on the puzzle theme or length, it fits hundreds of words. See all solutions →

#5

"Man's name."

Ambiguity Score

147 possible answers

Common Answers

IAN, IRA, SILAS, YVON, ALAN, ...

This clue is notoriously vague. Depending on the puzzle theme or length, it fits hundreds of words. See all solutions →

#6

"START OF A RIDDLE"

Ambiguity Score

143 possible answers

Common Answers

DDDDDDDDDDDDD, WHATCAPITALIN, WHATWORDMEANING, WHATWORD, WHATCATCHERS, ...

This clue is notoriously vague. Depending on the puzzle theme or length, it fits hundreds of words. See all solutions →

#7

"Riddle, part 2"

Ambiguity Score

127 possible answers

Common Answers

CONTAINSTHEFIVE, DDDDDDDDDDDDDD, EUROPEISMADEOF, SMALLBECOMESA, DIDTHESNAIL, ...

This clue is notoriously vague. Depending on the puzzle theme or length, it fits hundreds of words. See all solutions →

#8

"End of the riddle"

Ambiguity Score

124 possible answers

Common Answers

ANDANACTRESS, ANYORDER, DDDDDDDDDDDDD, MENSNICKNAMES, THELASTFLETTERS, ...

This clue is notoriously vague. Depending on the puzzle theme or length, it fits hundreds of words. See all solutions →

#9

"Man's nickname"

Ambiguity Score

124 possible answers

Common Answers

ZEKE, DAVIE, NAT, CLEM, MATT, ...

This clue is notoriously vague. Depending on the puzzle theme or length, it fits hundreds of words. See all solutions →

#10

"RIDDLE, PART 3"

Ambiguity Score

122 possible answers

Common Answers

DDDDDDDDDDDDD, LETTERSEFGHANDI, TWOCONSECUTIVE, WORDMEANINGHUGE, SAYWHENHE, ...

This clue is notoriously vague. Depending on the puzzle theme or length, it fits hundreds of words. See all solutions →

Stuck on one of these?

Don't guess. Our engine knows all 310 variations of "Girl's name".

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