Monday, July 21, 2014

Stephen Sondheim's Crossword Puzzles

I've become obsessed with the cryptic crossword puzzles that Stephen Sondheim devised for New York Magazine in 1968-69. I'm slowly working my way through solving them. This article gives a pretty good overview of the Sondheim/puzzle story. In 1980 the puzzles were collected and published in the almost-impossible-to-find (or afford) book Stephen Sondheim's Crossword Puzzles from New York Magazine. (If you're remotely interested in this topic, you'll want to read Sondheim's explanation of why cryptic crossword puzzles are so much better than regular ones.)

As my research has shown, there were 42 Sondheim puzzles published in New York. (The book has 41, omitting the puzzle "Un-American", which has a central theme that became outdated just a few months after magazine publication.) 34 of the puzzles are readily available online, through Google Books. Below is my chronological list of which puzzles appeared in which issues, starting with New York's first issue. There were a few "holes" in 1968 in which puzzles were contributed by other people, at least one by Richard Maltby Jr., but I'm only concerning myself with the Sondheim puzzles here. In 1969 Sondheim switched to an every-third-week schedule, but apparently even that was too much for him to maintain as he was busy writing Company.

Note: The published errata notwithstanding, there are still some mistakes in these puzzles. These may be due more to New York's editors than to Sondheim himself. But even in the book, mistakes went uncorrected. I solved one such error here.


April 22: 3 Downs (solution 5/6/68)
May 20: Misprints (solution 6/3/68)
June 3: Vicious Circles (solution 6/17/68)
June 17: Chop Logic (solution 7/8/68)
July 8: Sixes and Sevens (solution 7/29/68)
August 5: Assemblage Line (solution 8/26/68)
September 16: Word Games (solution 10/7/68)
September 23: 1 Across (solution 10/14/68)
October 7: New Directions (solution 10/28/68)
October 28: Head-Hunting (solution 11/18/68)
December 9: Treasure Hunt (solution 1/6/69)
December 16: Perspectives (solution 1/27/69)
December 23: Christmas Competition (solution 1/27/69)


January 6: Un-American (solution 2/17/69)
January 27: Vicious Circles II (solution 2/17/69)
February 17: Faces (solution 3/10/69)
June 23: Critical Birds (solution 7/14/69)
July 14: Sixes and Sevens II (solution 8/4/69)


  1. Wow, what a delight! I was addicted when they came out, have several stashed in my files somewhere, and can't wait to get to do them again. thank you!!

  2. Thank you for posting these...have done the first two and looking forward to more!

  3. Hi Galen, thanks for sharing these! I was the original poster who put them up back in 2011, and inspired that NY Times article you link to. I'm glad to see they have found their way on to the web in a more legal format!


  4. I had the book at one time, when I hadn't really learned much about cryptics, particularly of the variety type. I wish I could find another copy, or that it would be republished! And when I say I had a book of Sondheim's puzzles, I get really weird looks from folks who think of him as Broadway and nothing else.