Matching Minds with Sondheim: How Puzzles Shaped a Musical Theater Legend with Barry Joseph (Ep. 135)

2026-05-19

What do crossword puzzles have to do with "Send in the Clowns"? More than you'd think. This episode, Shoshana is joined by Barry Joseph, author of Matching Minds with Sondheim, to explore Stephen Sondheim's lifelong obsession with puzzles and games, and how that obsession quietly shaped everything from his lyrics to his show structures to his closest relationships. In the "Why Is This So Good?" segment, Shoshana and Barry dig into "Good Enough to Eat" from Schmigadoon! Season 2. Music featured:

What do crossword puzzles have to do with "Send in the Clowns"? More than you'd think.

This episode, Shoshana is joined by Barry Joseph, author of Matching Minds with Sondheim, to explore Stephen Sondheim's lifelong obsession with puzzles and games, and how that obsession quietly shaped everything from his lyrics to his show structures to his closest relationships.

In the "Why Is This So Good?" segment, Shoshana and Barry dig into "Good Enough to Eat" from Schmigadoon! Season 2.

Music featured:

"Ten Years Old (The Fabulous Fifties, 1960)" from Sondheim Sings Vol. II (1946–1960)
"Hesitation (Reprise)" from Here We Are
"A Little Priest" from Sweeney Todd
"Good Enough to Eat" from Schmigadoon! Season 2

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