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.”
