Newspapers with the Most Challenging Crosswords: The Gold Standards

The Gold Standards

• The New York Times: Especially the Sunday puzzle; widely considered the benchmark.
• The Wall Street Journal: Daily puzzles often match NYT difficulty.
• The Los Angeles Times: Sunday edition known for trivia depth and complexity.

Other Excellent Challengers

• The Boston Globe (Sunday)
• The San Francisco Chronicle (daily, wordplay-heavy)
• The Chicago Tribune (varied difficulty)
• The Washington Post (daily, mix of classic & tough)
• The Independent & The Guardian (UK; Guardian is more accessible)

Digital Options with Difficulty Tiers

• NYT Crossword app, WaPo Crossword app, Guardian Crossword site, The Crossword Club.

Tip: Start with NYT/WSJ, then experiment to match your solving style.