On Halloween night, 1968, a flock of twenty eminent New Yorkers burst out of the door of Stephen Sondheim’s Turtle Bay town house. The group included the Broadway producer Harold Prince, the playwright Arthur Laurents, the composer Mary Rodgers, and the actors Lee Remick and Roddy McDowall. Divided into teams of five, the guests filed into four limousines. They’d been given maps of the city, and objects including string, pins, and scissors, as well as a piece of advice. “Keep talking to each other,” their host had told them. “Do not try to solve these things individually.” Sondheim, at thirty-eight, had already written the lyrics for “West Side Story” and “Gypsy,” but he had not yet revolutionized the American musical with his dense, urbane scores for “Company,” “Follies,” and “A Little Night Music.” In the meantime, he was plying one of his lesser-known talents: designing elaborate treasure hunts.
Sondheim had devised the hunt with the actor Anthony Perkins; they had met through Perkins’s partner, Grover Dale, who’d been one of the Jets in “West Side Story,” on Broadway. In the weeks before the hunt, Sondheim and Perkins had labored over clues. They planted envelopes around town: under a park bench, behind the pins in a bowling alley. Perkins had a cache of leftover campaign posters for Eleanor Clark French, a local politician who had run unsuccessfully for Congress a few years earlier, and the two men hung them in strategic locations, to give the players visual hints that they were on the right track.
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All the clues were based on logic. Mary Rodgers later recalled driving up to a brownstone on East Seventy-third Street, where her team heard music wafting through the door. It was the opening phrase of “One for My Baby,” on repeat. The lyric: “It’s quarter to three, there’s no one in the place . . .” The solution: 245, which matched another address on the map. At one building, players were greeted by Perkins’s mother, who served them cake and tea. Someone was about to bite into the cake when a teammate spotted a clue written at the bottom of the teacup: “You can’t have your cake and eat it, too.” They put their cake slices together, and the solution was spelled out in icing.
The evening, which Sondheim and Perkins titled the Eleanor Clark French Memorial Treasure Hunt, became legendary. In the coming decades, Sondheim designed more treasure hunts. In 1973, when “A Little Night Music” was about to move from the Shubert to a bigger house, he and Perkins devised a farewell-to-the-Shubert hunt that sent the cast scouring the theatre, with clues based on the script. (One was “Where Petra’s petticoats are.” A lyric described them as “away up high,” which meant that the next stop was the balcony.) There was a fax-based hunt in the eighties, for which Sondheim enlisted Stephen Fry and his fax machine, and a dinosaur-themed hunt at the American Museum of Natural History. In 1995, to raise money for the Millay Colony for the Arts, Sondheim created a hunt at a Manhattan clubhouse. At each location, players would gather scraps of Edna St. Vincent Millay’s poems, which, mashed together, revealed a double acrostic: “THE TREASURE LINGERS IN MY LOCKER,” leading the winners to a gym locker labelled “Millay.”
Sondheim’s last major treasure hunt was in 2013, at a birthday gala for his friend Perry Granoff. Attendees were gathered on the grand tier at New York City Center. Each team was given an envelope containing twelve brainteasers—rebuses, letter grids—that could be solved in any order, leading to sites around the theatre. As the teams puzzled, the octogenarian game master would wander by, dispensing gnomic pointers like “Think laterally.” Clue No. 8, called Perry’s Confusion, was a jumble of letters, “AAEFINNORTTUW,” along with the hint “The first word alternates vowels and consonants and has no repeated letters.” 1 (The solutions to this and other numbered clues can be found at the end of this piece.) Clue No. 12, Perry’s Favorite Shows, Except One, was a list of six Broadway musicals: “A Little Night Music,” “Cats,” “Fiorello!,” “Kiss Me, Kate,” “The Music Man,” and “South Pacific.” (“Cats,” presumably, was the show that Granoff disliked.) Players had to arrange them in chronological order and then find an acrostic using their first or last letters, read either top to bottom or bottom to top. 2
At each location, participants would find a theatre ticket, which led to a seat in the house containing a letter. The first team to collect and unscramble all twelve letters uncovered the location of the grand prize: a gold box containing a T-shirt printed with Granoff’s face and the words “I won the treasure.” “Are you kidding me?” one of the underwhelmed victors said, upon opening the box. The real prize, of course, was the privilege of having played.
Sondheim’s death, in 2021, has occasioned a flurry of books about his life and his singular influence on musical theatre. Only Barry Joseph has zeroed in on his sideline as a puzzles-and-games enthusiast. In his clever and appropriately obsessive “Matching Minds with Sondheim: The Puzzles and Games of the Broadway Legend” (Bloomsbury), Joseph conducts a treasure hunt of his own, rummaging through memoirs and archives and surveying friends, collaborators, party planners, and jigsaw-puzzle designers to reconstruct a part of Sondheim’s œuvre which was mostly confined to his social circle. “It’s a whole side of me nobody knows,” Sondheim once said, though he did his best to downplay what he saw as a committed pastime. Constructing puzzles, he insisted, was “a minor form of a minor art.”
Joseph disagrees. “His puzzles and games should receive the same thoughtful consideration as his music,” he writes, while conceding that they formed “a footpath that ran along the main road of his life, one he would frequently travel.” Joseph, who designs educational games and co-founded the Games for Change Festival, is a polymath himself. His previous books include a history of seltzer, and he’s the director of something called the Brooklyn Seltzer Museum. The new book is itself a sort of puzzle box. The dedication is a word puzzle that I have yet to solve, and the back third comes with instructions on how to throw your own Sondheimian game night. Braver souls might try a parlor game called Hostilities, which Sondheim used to play with his nineteen-sixties set. Every player was given a number and slips of paper and wrote impertinent questions intended for each of the others. Example: “Who’s smarter, your spouse or your collaborator?” The slips were delivered, answered in writing, and then anonymized and thrown in a bowl. Each was then read aloud, as players guessed who had asked and answered which nosy questions. The game frequently ended in tears.
Most of the book, though, is devoted to a “ludological biography” of the great man: a life in puzzle pieces, hitherto unassembled. Sondheim may not have considered his puzzles and games to be on par with his musicals, but they open a window onto his bustling mind, one with a compulsive need to challenge itself. For years, he did crossword puzzles not in pencil or pen but in his head—the paper was left blank—and visitors reported having seen an all-white jigsaw puzzle on his coffee table. Sondheim possessed what he called a “curious and perverted ability” to scramble letters on sight. As a boy, he once walked past a movie theatre advertising Cinerama and turned to his father to remark, “Oh, those are the letters in ‘American.’ ”
Meryle Secrest, in her 1998 biography of Sondheim, theorized that his interest emerged from the trauma of his parents’ divorce, when he was ten—a time when, the composer said, “nothing made sense any more.” Puzzles, Secrest writes, reassured him that “a world in fragments could be reassembled, however painfully, and that a key existed to every riddle if he searched diligently enough.” Joseph sifted through Secrest’s papers, at Yale, and found the moment that Sondheim had this revelation in their interviews. “Maybe, you know, when my own world went into chaos, I spent the rest of my life trying to put the pieces together and make form out of it,” he told her. For years, when asked about his penchant for puzzles, he’d say that they create “order out of chaos.” Art, he would explain, did the same.
Just as Sondheim’s parents were breaking up, he found a mentor and surrogate father in Oscar Hammerstein II, a family friend and neighbor in Bucks County, Pennsylvania. “I started chess late in life, and my teacher was an eleven-year-old boy,” Hammerstein once said. “It took me three years to be able to beat him.” (Sondheim had learned how to play from the husband of Hammerstein’s cook.) Along with opening his protégé’s mind to the theatre, Hammerstein taught Sondheim the game anagrams, in which players take turns flipping over lettered tiles and using them to form words. Later, Leonard Bernstein introduced Sondheim to a variation called cutthroat anagrams, which is more of a free-for-all: there are no turns, so anyone can snatch the new letter and make a word. Sondheim preferred this version, since it was about quickness rather than luck. Nina Bernstein, the composer’s youngest child, recalled getting “thrown in with the lions.” She finally triumphed in her twenties, when she spotted an “M” tile and a “B” tile and stole Sondheim’s word “saturated,” to form “masturbated.”
In the fifties, as Sondheim was writing the lyrics to Bernstein’s music for “West Side Story,” he introduced the older man to cryptic crosswords, a form popular in England but little known in America. The pair had different modes of collaboration—Bernstein preferred to work in the room together, while Sondheim would rather be apart—but the cryptics that arrived every week in the British magazine The Listener helped bridge the divide. “We would meet on Thursday and spend the first couple of hours doing the puzzle together,” Sondheim recalled, “and then would get to work.” When Bernstein was turning fifty and looking for a successor at the New York Philharmonic, Sondheim created an intricate three-part board game called the Great Conductor Hunt, in which players could compete for the job. The third stage, Podium, was a three-dimensional Lucite maze with a miniature Lenny in the center, holding a baton.
Sondheim had begun designing board games in his teens. He sent an idea to Parker Brothers and then considered suing when the company put out a game—Park and Shop—that he thought copied his. When he was twenty-three, he created a board game alternately called Stardom or Camp, in which players compete to succeed in Hollywood by sleeping their way to the top—the winner beds Norma Desmond—while affixing colored sequins to their faces. (The game was uncovered intact after his death, as his belongings were being prepared for auction.) Another, known as the Game of Hal Prince, or Producer, gamified the business of Broadway, with points allotted for good reviews and wild cards that ribbed Sondheim’s contemporaries. (Jerome Robbins abandons the show to see his therapist.) Sondheim also collected antique board games; his first acquisition, a gift, was a nineteenth-century amusement called the New and Fashionable Game of the Jew, which featured an antisemitic caricature perched over gold coins. Visitors to Sondheim’s Manhattan home would marvel at the game boards framed on the walls—until 1995, when the bulk of them were destroyed in a house fire.
During the sixties, when Sondheim was not yet entrenched on Broadway, his puzzler’s brain seemed to be working overtime. He appeared as a celebrity contestant on TV game shows, including “Play Your Hunch” and “The Match Game.” On a recently unearthed episode of “Password,” from 1966, he plays opposite Lee Remick, who had starred in Sondheim’s show “Anyone Can Whistle.” In one round, he has to guess a secret word based on single-word clues that Remick feeds him. “Picture,” she says. Sondheim, cool as a cobra, supplies the correct answer: “Etching.”
In 1968, the editor Clay Felker was launching a new magazine, to be called New York, and he asked a mutual friend, Gloria Steinem, to see if Sondheim would oversee its puzzles page. Over a year and change, Sondheim constructed forty-two cryptic crosswords for the magazine. In the inaugural issue, he gave readers a primer. “The kind of crossword puzzle familiar to most Americans is a mechanical test of tirelessly esoteric knowledge,” he wrote. A cryptic clue, in contrast, has a “cleverness, humor, even a pseudo-aphoristic grace.” Each clue was a puzzle unto itself, often divided into two parts. One clue, from a Sondheim cryptic titled “Chop Logic,” goes “Broken harmonicas found floating in Manhattan.” 3 “Broken” implies that “harmonicas” is an anagram, and “floating in Manhattan” is a sideways description of the solution. In 1969, Sondheim quit his post at New York to focus on “Company,” but his contributions helped popularize the form Stateside. No less an authority than Will Shortz, the crossword editor of the Times, considers Sondheim “the father of cryptic crosswords in America.”
His most fertile ludological invention, however, may be something he called the Murder Game. He’d been rankled by the traditional party game in which one person is designated the murderer and the players have to deduce who has “killed” someone else. “The problem with most murder games,” Sondheim complained, “is you have nothing to do except maybe giggle around in the dark.” In 1965, he was visiting his friend Phyllis Newman, who was stuck in Detroit in a Frank Loesser musical that was about to close out of town. Sondheim asked how he could cheer her up. She said to throw her a party back in New York: “Invent a game.”
Sondheim got to work at eight o’clock one night, devising a version of the murder game in which all the players would have to use their wits to untangle the mystery. When he looked up, it was around seven the next morning, and he’d done it. A group was assembled at Perkins’s town house, on West Twenty-first Street. Each player drew from a deck of cards to receive a number and was then given an envelope, with individual instructions to go to a particular room and search for a clue. The murderer was told where to find a gun. By coincidence, Perkins, five years after stabbing Janet Leigh in the shower in “Psycho,” wound up being the murderer—and “killed” another guest, the English playwright Peter Shaffer, in the bathroom, no less. The surviving guests then returned with their clues—photos of seemingly random objects—and had to work out who’d killed Shaffer. (Shaffer joined them after smoking two cigarettes on the bathroom floor.)
The next time Sondheim was in London, Shaffer got him to re-create the Murder Game for his brother, the writer Anthony Shaffer. In 1970, Anthony’s play “Sleuth,” set in a mystery writer’s mansion strewn with puzzles, opened in London. The original title: “Who’s Afraid of Stephen Sondheim?” Two years later, “Sleuth” became a movie starring Laurence Olivier. When Sondheim met Olivier, soon after it was shot, the actor told him, “I’m delighted to meet you. I’ve been playing you.”
At about the same time, another Sondheim playmate, the director Herbert Ross, asked him to write a screenplay based on his Murder Game. Sondheim and Perkins collaborated on the script, which became “The Last of Sheila,” a 1973 whodunnit directed by Ross and starring Raquel Welch. The film is set on a yacht cruising the Mediterranean, where the host, a producer named Clinton Greene (James Coburn), has convened a group of acquaintances one year after his wife, Sheila, was killed in a hit-and-run. Every night, the boat docks, and the guests, each of whom harbors a dirty secret, are sent into a different port city to solve a puzzle, using clues that borrow elements of Sondheim’s treasure hunts. Midway through, Clinton is bumped off at a monastery while dressed as a monk in Raquel Welch drag, and his guests must unravel the crime.
For most Sondheim fans, “The Last of Sheila” is a curio, wedged between “A Little Night Music” and “Pacific Overtures.” (It’s worth watching just for the performance of Dyan Cannon, as a thinly veiled version of the Hollywood agent Sue Mengers.) To Joseph, it’s a glimpse of what Sondheim the puzzle maestro could do with a budget and an all-star cast. Its plot is reminiscent not only of the Murder Game but of Joseph’s book: the master of ceremonies has died, and the biographer is left to sort out the clues. “Sheila” prompted one moviegoer to stage a real multi-city scavenger hunt, which inspired the 1980 film “Midnight Madness,” which then inspired another real-life contest, which spawned the 1997 thriller “The Game,” directed by David Fincher. And if elements of “Sheila” sound familiar—the Mediterranean isle, the enigmatic host imposing games on his guests—that’s because Rian Johnson drew on “Sheila” when writing his “Knives Out” sequel “Glass Onion,” for which Sondheim filmed a cameo months before his death.
Like the clue that gives away Clinton’s killer, the most meaningful legacy of the Murder Game is hiding in plain sight. In “Sunday in the Park with George,” Sondheim’s 1984 musical, the painter Georges Seurat sings a ballad called “Finishing the Hat,” about how artists become so immersed in their art that they neglect the world around them. (“There’s a part of you always standing by, / Mapping out the sky.”) It’s often thought of as Sondheim’s most confessional song, an ode to the thrill and the cost of creativity. However, it was written not about the flow state of composing but about Sondheim’s experience devising the Murder Game in 1965, “trancing out” from dusk till dawn. “I had left the planet for eleven hours,” he later told the radio host Terry Gross, “completely absorbed in a world of instructions, gunshots, diagrams, and clues.”
What, if anything, does all this puzzling tell us about Sondheim’s musicals? Joseph gets around to them in an appendix, for which he polled fans online to catalogue the games within the shows. “A Little Priest,” the Act I finale of “Sweeney Todd: The Demon Barber of Fleet Street,” from 1979, is a battle of wordplay between Sweeney and his accomplice, Mrs. Lovett, as they imagine the varieties of men they plan to bake into pies. (“Or we have some shepherd’s pie peppered / With actual shepherd on top!”) The first act of “Sunday in the Park with George” ends with trees, parasols, and park-goers snapping into place like jigsaw-puzzle pieces to form Seurat’s masterwork “A Sunday on La Grande Jatte.” “Into the Woods,” written in the eighties, as Sondheim was getting into computer puzzle games, sends its heroes, a baker and his wife, on a fairy-tale scavenger hunt: to break a witch’s spell, they must find such items as Little Red Riding Hood’s “cape as red as blood” and Cinderella’s “slipper as pure as gold.”
Sondheim’s final musical, “Here We Are,” produced posthumously in 2023, is based on a pair of Luis Buñuel films. As Joseph observes, Act I, in which a group of bougie friends search in vain for a place to order brunch, resembles a board game. Act II, in which they find themselves in an embassy that they are mysteriously unable to leave, is akin to an escape room—a live-action gaming trend that interested Sondheim late in life, when he organized escape-room outings with friends like Mia Farrow and Bernadette Peters.
“All art—symphonies, architecture, novels—it’s all puzzles,” Sondheim told Stephen Schiff in this magazine, in 1993. “The fitting together of notes, the fitting together of words have by their very nature a puzzle aspect.” Lyricists, like cruciverbalists, have to arrange words within a restrictive space, aligning stress and syllable and rhyme. The same mind that was constructing cryptic crosswords for New York was rhyming “personable” with “coercin’ a bull,” in “You Could Drive a Person Crazy,” from “Company.” Then, there’s the game master’s instinct to entertain—to challenge without stumping. “A bad jigsaw puzzle is where people put five pieces together and say, ‘Oh, I see. It’s a cow,’ ” he told Schiff. “You don’t want everybody ahead of you all the time. Same thing with plotting a play. If the people are ahead of you, they’re looking at their watches until you get to where they already are.” Musicals were Rubik’s Cubes to be solved: when to cut a song, where to add a laugh. As Sondheim’s frequent collaborator James Lapine said, “He loves solving why things worked and why they didn’t.”
Sondheim’s analytical bent earned him a reputation as being cold and cerebral, but, if his musicals are about anything, they’re about the puzzle of existence. How to unsnarl the emotions that play tug-of-war with our souls? In “Into the Woods,” Cinderella debates whether to flee the prince or let him catch her on the palace steps. “You’ll just leave him a clue,” she concludes. “For example, a shoe.” Or take Bobby, the commitment-phobic Manhattanite at the center of “Company.” It takes him two acts to work out the mystery of his own thwarted longing. In “You Could Drive a Person Crazy,” his three paramours sing, like stymied crossword players, “Exclusive you, / Elusive you, / Will any person ever get the juice of you?”
Was Sondheim himself as exclusive, as elusive? By his playmates’ accounts, he mellowed as the decades went on, from the enfant terrible who subjected his friends to Hostilities to the éminence grise roaming through the City Center crowd, a satisfied grin on his face. To the players of his games, according to Joseph, he was both “devious adversary” and “number one cheerleader.” Bernstein may have put it best, in a poem that he wrote for Sondheim’s twenty-seventh birthday, while they were at work on “West Side Story”:
Notice anything about the first letters of those lines? Naturally, the whole poem is an acrostic, spelling out S-T-E-P-H-E-N S-O-N-D-H-E-I-M. It takes a puzzler to know one. ♦
