The Most Difficult Crossword Puzzle, Ranked

Voting rules: Choose the crossword puzzle you think is the most difficult!

Updated on Apr 23, 2024 06:37

Many avid crossword enthusiasts often find themselves puzzled by the complexity and challenge posed by certain cryptic crosswords. These puzzles not only stretch one's vocabulary but also test problem-solving skills and lateral thinking. Curiously, without a consensus on which puzzles are the most arduous, individuals might not know where to focus their energy or how to challenge themselves further. By participating in the ranking of the hardest crossword puzzles, users can both express their own experiences and also lean on the insights of others. This communal interaction helps in sculpting a clearer guide to which crosswords stretch the intellect the most. As votes accumulate, the list dynamically shifts, offering fresh perspectives and new challenges for enthusiasts looking to push their limits.

What Is the Most Difficult Crossword Puzzle?

1

81
votes
The New York Times Saturday crossword puzzle

The New York Times

Widely considered the most challenging crossword puzzle, the Saturday edition of The New York Times crossword puzzle has a reputation for being the most difficult. The clues are often obscure and require a vast knowledge of trivia and wordplay.
The New York Times Saturday crossword puzzle is renowned for being one of the most challenging crossword puzzles.

Difficulty Level: Very challenging

Grid Size: 15x15 squares

Number of Clues: Around 70-80 clues

Theme: Usually has a theme

Word Count: Usually around 72-140 words
2

28
votes
The LA Times Sunday crossword puzzle

Another popular and challenging crossword puzzle, the Sunday edition of The LA Times crossword puzzle features a mix of challenging clues and themes.
The LA Times Sunday crossword puzzle is known for being one of the most challenging crossword puzzles published in the United States. It offers a stimulating and enjoyable experience for avid crossword enthusiasts who seek a mental challenge. With its clever clues and intricate grid, this puzzle tests the solver's vocabulary, knowledge, and problem-solving skills.

Publication Date: Every Sunday

Grid Size: 21x21 squares

Number of Clues: 70-80 clues

Difficulty Level: Challenging

Theme: Varies each week
3

22
votes
The Wall Street Journal Saturday puzzle

Mike Shenk

Known for its cryptic clues and difficult themes, the Saturday edition of The Wall Street Journal crossword puzzle is a true test of crossword-solving skills.
The Wall Street Journal Saturday puzzle is known to be one of the most challenging crossword puzzles.

Difficulty Level: Very difficult

Size: 21x21 grid

Theme: Usually contains a theme with wordplay or puns

Word Count: Around 70-80 words

Clues: Cryptic and tricky clues
4

18
votes
The Listener crossword puzzle

A British crossword puzzle that is renowned for its difficulty, The Listener crossword puzzle features complex clues and requires a deep knowledge of British culture and language.
The Listener crossword puzzle is a weekly puzzle published in The Times newspaper. It is known for its challenging nature, requiring both ingenuity and perseverance to solve. Each puzzle is crafted with a unique theme or twist, making it one of the most difficult crossword puzzles available.

Publication: The Times newspaper

Difficulty Level: High

Frequency: Weekly

Theme-Based: Yes

Twist: Yes
5

20
votes
The American Values Club crossword puzzle

Francis Heaney

A subscription-based crossword puzzle, the American Values Club crossword puzzle is known for its challenging themes and complex wordplay.
The American Values Club crossword puzzle is a challenging crossword puzzle that focuses on progressive and inclusive themes.

Difficulty level: Advanced

Size: 15x15 or 21x21 grid

Theme: Progressive and inclusive

Clue style: Modern, sometimes with pop culture references

Word count: Generally higher than average (e.g., over 70 words)
6

12
votes
The Enigma crossword puzzle

A cryptic crossword puzzle that is published in The Sunday Times of London, the Enigma crossword puzzle is notorious for its challenging clues and themes.
The Enigma crossword puzzle is widely regarded as one of the most difficult crossword puzzles ever created. Its complex and intricate design challenges even the most experienced crossword enthusiasts, pushing their problem-solving skills to its limits.

Difficulty Level: Extremely Difficult

Grid Size: Usually 15x15, but can vary

Number of Clues: Varies, but typically ranges from 75 to 100

Cryptic Clues: Yes

General Knowledge Clues: Yes
7

9
votes
The Times of London crossword puzzle

A daily crossword puzzle that is published in The Times of London, this crossword is known for its challenging clues and themes.
The Times of London crossword puzzle is known for its challenging nature and high level of difficulty. It is a popular crossword puzzle that features complex clues and requires a wide range of knowledge to solve.

Publication: The Times of London

Grid Size: 15x15 or 17x17

Clue Complexity: High

Difficulty Level: Very challenging

Frequency: Daily
8

8
votes
The Boston Globe Sunday crossword puzzle

Henry Hook

Another challenging Sunday crossword puzzle, The Boston Globe's Sunday crossword puzzle features a mix of challenging clues and themes.
The Boston Globe Sunday crossword puzzle is a challenging crossword puzzle featured in The Boston Globe newspaper. It has gained a reputation for being one of the most difficult crossword puzzles in the world.

Publication: The Boston Globe

Difficulty Level: Extremely Difficult

Size: 21x21 squares

Theme-based: Yes

Clue Count: Around 140 clues
9

12
votes
The Guardian crossword puzzle

The Guardian

A daily crossword puzzle that is published in The Guardian newspaper, this crossword is known for its challenging clues and themes.
The Guardian crossword puzzle is a widely acclaimed crossword puzzle featured in The Guardian newspaper. It is known for its challenging clues and diverse range of themes. Solving this crossword puzzle requires a high level of vocabulary, general knowledge, and lateral thinking.

Difficulty Level: Difficult

Frequency: Daily

Size: 15x15 grid

Clue Variety: Cryptic and General Knowledge clues

Themes: Diverse range of themes
10

7
votes
Tonyle · Public domain

The Cryptic crossword puzzle

Arthur Wynne

A type of crossword puzzle that features cryptic clues, this type of crossword puzzle is known for its difficult wordplay and requires a deep knowledge of language and culture.
The Cryptic crossword puzzle is a type of crossword puzzle that is known for its tricky and challenging clues. It is designed to test the solver's ability to decipher cryptic clues, which often involve wordplay, double meanings, anagrams, and other forms of word manipulation.

Complexity: High

Clue style: Cryptic

Wordplay: Heavy emphasis

Double meanings: Common

Anagrams: Frequent

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Discussion

Ranking factors for difficult crossword puzzle

Grid Size

Larger grids generally offer a more significant challenge due to the increased number of clues and intersections between words.
Clue Complexity

Difficult puzzles often have more ambiguous or cryptic clues, requiring solvers to make connections between seemingly unrelated words and concepts.
Vocabulary

Challenging puzzles tend to use less common or obscure words, requiring a more extensive vocabulary range to solve.
Theme Density

The more interconnected the theme of the crossword, the harder it is to solve, as it requires solvers to understand the overall concept behind the puzzle.
Word Length

Longer words with fewer known letters can be more challenging to solve, as they require more knowledge and guessing to determine the correct answer.
Intersections

The more words intersecting, the easier it is to solve the puzzle. Hence, a difficult puzzle will have fewer intersections, making it more challenging for solvers to use deduced letters to find answers.
Clue Format

Cryptic crosswords are generally more challenging than standard crosswords due to their complex wordplay clues, whereas standard crosswords rely on general knowledge and definitions.
Constructors' Style

The style of the person who creates the crossword can have a significant impact on its difficulty level. Some constructors are known for their challenging puzzles, while others aim for more accessible grids.
Pop Culture References

Difficult puzzles may include obscure or dated cultural references, making it more challenging for solvers to identify correct answers.
Abbreviations and Acronyms

The usage of abbreviations, acronyms, or non-standard word constructions can increase the challenge for solvers to decipher the intended word or phrase.

About this ranking

This is a community-based ranking of the most difficult crossword puzzle. We do our best to provide fair voting, but it is not intended to be exhaustive. So if you notice something or Crossword is missing, feel free to help improve the ranking!

Statistics

2732 views
197 votes
10 ranked items

Movers & Shakers

The New York Times Saturday crossword puzzle
The LA Times Sunday crossword puzzle
The Enigma crossword puzzle
The Cryptic crossword puzzle

Voting Rules

A participant may cast an up or down vote for each Crossword once every 24 hours. The rank of each Crossword is then calculated from the weighted sum of all up and down votes.

More information on most difficult crossword puzzle

Crossword puzzles have been a popular pastime since their creation in the early 20th century. They challenge our vocabulary, intellect, and problem-solving skills. However, not all crossword puzzles are created equal. Some are notoriously difficult, with obscure clues and complex answers that leave even the most seasoned puzzlers stumped. Determining the most difficult crossword puzzle is subjective, as everyone has different strengths and weaknesses when it comes to wordplay. Some puzzles may be difficult due to the use of rare words or phrases, while others may require a deep knowledge of pop culture or history. However, there are a few puzzles that have gained a reputation as being among the most challenging. The New York Times Saturday crossword, for example, is often considered the gold standard of crossword puzzles and is notorious for its difficulty level. The cryptic crossword puzzles found in British newspapers such as The Guardian and The Times are also notoriously challenging, requiring a different set of skills to solve than traditional crossword puzzles. Whether you're a seasoned crossword puzzler or just starting out, tackling a difficult puzzle can be a satisfying and rewarding experience. Who knows, you may even discover a new favorite puzzle to add to your collection of completed challenges!