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Sondheim's fascination with the theater reaches back to a day in 1939 when his father took Stephen, 9, to see a Broadway musical, Very Warm for May. He recalls, "The curtain went up and revealed a piano. A butler took a duster and brushed it up, tinkling the keys. I thought that was thrilling." That moment, a few months before his parents' divorce, was one of the few distinctly happy ones from a latchkey childhood: "I did not have an unhappy time, because it literally did not occur to me that other people had a family life. I saw ((my parents)) occasionally at night and on weekends, and I thought every child in New York lived that way." Sondheim's father was a manufacturer of medium-price dresses, and his mother was the firm's designer. "We lived very nicely," he recalls, "on Central Park West in Manhattan, but at the back of the building. After my father remarried, he moved to Fifth Avenue, still at the back of the building. From him I get my tendency to pessimism. He always looked at the black side, imagined the worst that could happen. Eventually my stepmother and I forced him to retire, and I'm sorry to say I think it killed him -- he missed the worry."
Stephen's mother won custody of him in the divorce and forbade him to have any contact with his father. "She would have members of her family follow me to see if I met him in secret," he recalls. "She would telephone his apartment to see if I answered, then hang up. I was a substitute for him, and she took out all her anger and craziness on me. From her I get my tendency to hysteria. It was not a great relationship." It never improved: Sondheim has helped his mother financially but has gone through long periods of not speaking to her, and regales friends with darkly comic tales of her attempts to rile him -- making mementos of his shows, for example, but pointedly omitting the flops. Mary Rodgers, daughter of Richard Rodgers and one of Sondheim's oldest friends, describes Sondheim's propensity for writing "eloquent, deliberately mean, really hooty little thank-you notes," and quotes a sample: "Dear Mary and Hank, Thanks for the plate, but where was my mother's head? Love, Steve."
A couple of years after the divorce, however, Sondheim's mother made a doting gesture that transformed his life. Stephen, then 12, had made a new friend named Jamie Hammerstein, son of Oscar, the lyricist of Very Warm for May, and was invited to the family farm in Doylestown, Pa., for a weekend. The weekend turned into a summer and, not long after, Mrs. Sondheim bought a house in Doylestown so Stephen could live there year-round. She continued to commute to Manhattan, often stayed there during the week and on weekends typically brought along guests. But as Jamie Hammerstein recalls, "by Christmas, Stephen was more a Hammerstein than a Sondheim." The pivotal relationship was with Oscar. Sondheim recalls that at 15 he showed Hammerstein a novice musical he had written: "Oscar said, 'It's the worst thing I have ever read -- but I didn't say it was untalented.' " What followed was the first installment of a years-long informal education.