This fall, Stephen Sondheim’s love of games and his genius for music came together—across two NYU campuses, two creative disciplines, and one shared idea: that the same design values that shaped his puzzles and parlor games also shaped his musicals.

In late September, students gathered at the NYU Game Center in Brooklyn for How to Play the Sondheim Way: A Parlor Game Workshop, a hands-on exploration of how the Broadway legend’s playful side can inspire our own creative practices. A week later, I crossed the river to the Graduate Musical Theatre Writing Program (GMTWP) in Manhattan, where the focus shifted from playing to composing—unpacking how Sondheim’s lifelong fascination with game mechanics found its way into his storytelling, structure, and collaboration. Together, the two events created a dialogue between play and craft, between puzzles and songs, between the way Sondheim designed and the way he composed.

Brooklyn: How to Play the Sondheim Way

Being introduced by Eric Zimmerman (almost made me cry)

Hosted at 370 Jay Street, the Game Center workshop invited both game-design and musical-theatre students to literally play their way into Sondheim’s mind. We began, fittingly, with a puzzle—an icebreaker adapted from one Sondheim himself once used for a 2011 treasure hunt at the American Museum of Natural History. Students had to find three others in the room to complete the solution, quickly discovering that the group itself was the puzzle’s missing piece; that fusion of intellect and connection—“moments of clarity” leading to “moments of connection”—became the night’s theme.

We moved through a history of Sondheim’s famous game nights, then dove into Jerome Robbins’s “Listening Game,” a deceptively simple exercise in focus and empathy. From there, I introduced what I call Sondheim’s Three Principles of Play:

• Generosity – designing not to show off your own cleverness but to help others recognize their own;

• Playfulness – creating a liminal space where surprise and laughter invite people to take risks, where play is not a verb but a noun, that is: play is not just a thing one does but a state of mind;

• Mentorship – challenging players just beyond their current abilities, but always with support.

We added four more design tips drawn from his practices—build a level playing field, maximize engagement for all, use “gotcha” mechanics carefully, and simulate real-world systems through play—and then put them to the test.

Students rotated through demonstrations of Bartlett’s, Sondheim’s adaptation of the parlor game Dictionary using Bartlett’s Familiar Quotations; Running Charades, a high-energy, all-play version of the classic; and finally The Murder Game, the intricate party mystery that inspired The Last of Sheila and even Sondheim’s song Finishing the Hat. Each round ended with the same reflective question: How does this game reflect Sondheim’s design values?

By the end of the evening, the answer was clear. Whether crafting lyrics or hosting friends, Sondheim approached design as an act of empathy. His games weren’t about just about winning—they were about learning how to play together.

Manhattan: Matching Minds at GMTWP

    When I joined Robert Lee and the students of GMTWP the following week–in a lovely black box theater on the edge of Washington Square Park–the energy shifted from dice and pencils to pianos and libretti—but the inquiry stayed the same. What happens when we view Sondheim not just as a composer-lyricist, but as a game designer whose mechanics live inside his songs?

Robert opened with a story I recount in Matching Minds with Sondheim: after the commercial failure of Merrily We Roll Along, Sondheim told James Lapine he might quit Broadway to design video games. That impulse, we discussed, wasn’t a detour—it was a revelation. From his childhood experiments analyzing board-game mechanics with Oscar Hammerstein’s son to his Atari sessions with collaborator John Weidman, Sondheim’s fascination with systems and rules paralleled the very structures of musical theater.

The conversation became interactive, almost a seminar-game in itself. Students identified where Sondheim’s seven design values (described above) show up not just in his parlor games but in his musicals. To test the idea, Robert cued up the opening scene of South Pacific, Hammerstein’s work that profoundly mentored Sondheim. Together we analyzed how the scene’s rhythms, reversals, and exposition embody those same mechanics: the AABA song form as a system, subtle “gotcha” modulations that surprise and delight, a generosity that ensures no audience member gets left behind.

Being Alive.

Then, to bring the ideas home, we turned to one of Sondheim’s most celebrated songs—Being Alive from Company. Robert played the earlier cut version, in which the protagonist, Bobby, rejects the vulnerability of connection, and then the final version, where he embraces it. Between the two, the room became a kind of design lab. We asked: what changed in the “game”? How did Sondheim revise the rules to shift the player’s (and listener’s) experience from isolation to intimacy? Students noted how the new version rebalanced the system—transforming a solo puzzle of self-protection into a multiplayer invitation to connect. It was a vivid demonstration of Sondheim’s values in motion: playfulness in structure, generosity toward the audience, and mentorship guiding both performer and listener toward emotional discovery.

From there, our dialogue turned personal. I shared how I first merged my own twin passions—education and games—through youth-media projects that eventually led to the creation of Games for Change, the festival and movement supporting social-impact game design. We discussed how, like Sondheim, creative people often live at the intersection of multiple callings. His so-called “midlife crisis” dream of becoming a video-game designer wasn’t escapism—it was integration.

Between Brooklyn and Manhattan: A Shared Design

Across both events, we kept moving between two worlds—games and songs, puzzles and performance, Jay Street and Washington Square—but the core idea never wavered. Sondheim’s artistic brilliance came not from separating his curiosities, but from letting them cross-pollinate. His approach to writing musicals was informed by game design: structure as system, collaboration as play, constraint as creativity. And his approach to games was informed by musical sensibility: rhythm, pacing, ensemble, revelation.

In Brooklyn, we played the principles. In Manhattan, we heard them resonate. And somewhere between those two boroughs, Stephen Sondheim’s two lifelong passions met once more—reminding us that art, like any great game, is at its best when it’s generous, playful, and meant to be shared.

Clara, Robert, and I.

Eric and I.