#22-Stephen Sondheim and Cryptic Crosswords episode artwork

EPISODE · Jan 30, 2026 · 1H 15M

#22-Stephen Sondheim and Cryptic Crosswords

from Matching Minds with Sondheim: The Podcast · host Barry Joseph & Broadway Podcast Network

Today’s topic: Stephen Sondheim’s passion for cryptic crosswords. Joined by guests Natan Last, Katie Grogg, Ben Zimmer, and Galen Fott, the conversation explores Sondheim's 1968 stint as the puzzle editor for New York Magazine, his influence on the American cryptic crossword scene, and the connections between his musical works and love for puzzles. Through reflections on prior interviews with Richard Maltby, Jr., Will Shortz, Colm Molloy, and, yes, Sondheim himself, the episode highlights Sondheim’s legacy in both theater and the world of wordplay. Make sure to get the book everywhere books are found, ⁠⁠or click here⁠⁠. 00:00 Introduction to the Podcast and Today's Topic 01:51 Meet the Guests: Crossword Enthusiasts and Experts 05:28 Discussing the New York Times Crossword Puzzle 07:51 Defining Cryptic Crosswords 10:30 Stephen Sondheim's Influence on Cryptic Crosswords 14:57 The British Cryptic Crossword Scene 22:29 Sondheim's Connection with British Crossword Constructors 32:39 Sondheim's Cryptic Crossword Journey Begins 33:33 American vs. British Crosswords: A Cultural Clash 34:41 Sondheim's Essay and Its Impact 35:44 Criticism and Parody in New York Magazine 41:34 Richard Maltby Jr. Takes Over 48:56 Sondheim's Cryptic Crossword Legacy 56:17 Modern Cryptic Crosswords and Sondheim's Influence 01:03:06 Final Thoughts and Reflections Special Links: Colm Molloy Ann Morrison Mateo Chavez Lewis “This Time It’s Crosswords (Not Cross Words) That Surface From Sondheim” New York Times, 2011. Galen Fott’s Blog Natan Last Ben Zimmer Katie Grogg Minute Cryptic Thanks to everyone who contributed behind the scenes to this episode: the Musical Stingers composed by Mateo Chavez Lewis, our line producer Dennis Caouki, and the theme song to our podcast with lyrics and music by Colm Molloy and sung by the one only Anne Morrison, currently on the road starring in Kimberly Akimbo. Learn more about your ad choices. Visit megaphone.fm/adchoices

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This episode is 1 hour and 15 minutes long.

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This episode was published on January 30, 2026.

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