However, most of the book is devoted to the “ludological biography” of a great man: a life consisting of puzzle pieces that have not yet been assembled. Sondheim may not have considered his puzzles and games the equal of his musicals, but they provide a window into his busy mind, which had a compulsive need to challenge itself. For years, he solved crossword puzzles not with a pencil or pen, but in his head (the piece of paper was left blank), and visitors reported seeing an all-white puzzle on his coffee table. Sondheim had what he called a “curious and perverse ability” to jumble letters in place. As a child, he once walked past a movie theater advertising Cinerama and turned to his father to remark, “Oh, those are the letters in the word American.” »
Meryl Secrest, in her 1998 biography of Sondheim, suggested that his interest arose from the trauma of his parents' divorce when he was ten—a time when, in the composer's words, “nothing made sense anymore.” Puzzles, Seacrest writes, convinced him that “a world broken into fragments could be put back together, albeit painfully, and that there was a key to every mystery if you looked hard enough.” Joseph looked through Seacrest's papers at Yale and found the moment when Sondheim made this revelation in his interviews. “Maybe, you know, when my own world fell into chaos, I spent the rest of my life trying to put the pieces back together and give it shape,” he told her. For years, when asked about his penchant for puzzles, he said they created “order out of chaos.” Art, he explained, did the same thing.
When Sondheim's parents separated, he found a mentor and surrogate father in Oscar Hammerstein II, a family friend and neighbor in Bucks County, Pennsylvania. “I started playing chess late, and my teacher was an eleven-year-old boy,” Hammerstein once said. “It took me three years to beat him.” (Sondheim learned to act from chef husband Hammerstein.) In addition to opening his protégé's mind to the theater, Hammerstein taught Sondheim the anagram game, in which players take turns turning over letter tiles and using them to form words. Later, Leonard Bernstein introduced Sondheim to a variation called “ruthless anagrams,” which is more of a public play: There are no turns, so anyone can grab a new letter and make a word. Sondheim preferred this version because it was about speed rather than luck. Nina Bernstein, the composer’s youngest child, recalled how she was “thrown into the midst of 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, when Sondheim was writing the lyrics to Bernstein's score 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 ways of collaborating—Bernstein preferred to work in the same room together, while Sondheim preferred to be apart—but the cryptic reports that appeared every week in the British magazine Listener helped bridge the gap. “We’d meet on a Thursday and spend the first couple of hours working on a puzzle together,” Sondheim recalled, “and then we’d get to work.” When Bernstein turned fifty and was looking for a successor at the New York Philharmonic, Sondheim created an elaborate three-part board game called “The Hunt for the Great Conductor” in which players could compete for the position. The third stage, “Catwalk”, was a 3D Lucite maze with a miniature Lenny in the center holding a baton.
Sondheim began developing board games when he was a teenager. He sent the idea to Parker Brothers and then considered suing when the company released a game called Park and Shop, which he believed was a copy of his game. When he was twenty-three, he created a board game, alternately called “Star” or “Camp,” in which players compete for success in Hollywood, working their way to the top (the winner sleeps on Norma Desmond) by attaching colored glitter to their faces. (The game was discovered intact after his death while his belongings were being prepared for auction.) Another game, known as “Hal Prince's Game,” or “The Producer's Game,” gamified the business on Broadway, awarding points for good reviews and wild cards that irritated Sondheim's contemporaries. (Jerome Robbins leaves the show to visit his therapist.) Sondheim also collected vintage board games; his first acquisition, a gift, was a nineteenth-century amusement called The Jew's New and Fashionable Game, which featured an anti-Semitic caricature above the gold coins. Visitors to Sondheim's Manhattan home marveled at the game boards hanging on the walls—until 1995, when most of them were destroyed in a fire.
In the sixties, when Sondheim had not yet established himself on Broadway, his puzzling brain seemed to be working overtime. He has appeared as a celebrity contestant on television game shows, including Play Your Hunch and The Match Game. In a newly discovered 1966 episode of Password, he stars opposite Lee Remick, who starred in Sondheim's show Anyone Can Whistle. In one round, he must guess a secret word based on one-word clues given to him by Remick. “Picture,” she says. Sondheim, cool as a cobra, gives the correct answer: “Etching.”
In 1968, editor Clay Felker was launching a new magazine called New Yorkand he asked a mutual friend, Gloria Steinem, to see if Sondheim would curate his puzzle page. Over the course of a year and change, Sondheim created forty-two cryptic crossword puzzles for the magazine. In the first issue, he gave readers a primer. “The crossword puzzle with which most Americans are familiar is a mechanical test of tireless esoteric knowledge,” he wrote. The cryptic clue, on the contrary, has “intelligence, humor and even pseudo-aphoristic grace.” Each clue was a riddle, often divided into two parts. One clue from the Sondheim mystery called “Chop Logic” reads: “There are broken accordions floating in Manhattan.” 3 “Broken” implies that “accordions” is an anagram, and “floating in Manhattan” is an extraneous description of the solution. In 1969, Sondheim left his post at New York focus on “Company”, but his contributions helped popularize the “Stateside” form. No less an authority than Will Shortz, crossword editor Timeconsiders Sondheim “the father of cryptic crosswords in America.”
