“Gee, I wish I had a dramatic answer,” Sondheim replied. “The fact is, I really like writing shows. It gets harder as time goes on. I thought I’d get more confident. And you’d think something like this Washington celebration would make me more confident, and it doesn’t. I think the more you write, the more you realize how much you don’t know. I think you get a view of yourself and somehow the weaknesses, the dangers of things like repetition, the feeling that you’ve written it all before, makes it harder to write. But in a way that also makes me want to write more because I want to overcome it. And, to put it sentimentally, there are just so many wonderful stories to tell, and I would really like to find some that would lend themselves to music that I haven’t heard before. That’s what I want. And that’s what I’m afraid of: writing music I’ve heard before.”
The day before he made his Broadway debut, as the 27-year-old lyricist of West Side Story, he wrote an uncharacteristically forthcoming letter to the musical’s composer, Leonard Bernstein: “You know—only too well—how hard it is for me to show gratitude and affection, much less commit them to writing,” he said, adding that friendship “is a thing I give and receive rarely.”
A photograph from that time shows Sondheim with a Blackwing pencil clamped in his mouth, a lock of dark hair drooping across his forehead and a touch of sadness in his eyes. He had grown up in a plush apartment building overlooking Central Park, the only child of Herbert and Janet Sondheim. His father, a self-taught pianist, played show tunes to relax. He was a benevolent if remote presence, largely preoccupied with managing a successful dress manufacturing company. Sondheim’s mother, who designed dresses for her husband’s company and also worked as an interior decorator, has been variously described as a woman with gumption and a sharp sense of humor, and also as a social climber who fibbed about her background and feigned a tony accent, according to Meryle Secrest’s 1998 biography, Stephen Sondheim: A Life. Sondheim’s parents traveled often, leaving their child in the care of a nurse or nanny; he had “an institutional childhood,” he once said. He started piano lessons at age 7 and showed a precocious interest in crossword puzzles and anagrams.
In 1940, when Sondheim was 10, his family imploded; his father walked out, and later moved in with another woman in New York. (Herbert Sondheim eventually remarried, had two more sons and died in 1966.) A jilted Janet Sondheim, according to biographer Secrest, did her best to poison her son’s relationship with his father, forbidding the boy from visiting his father in the company of his wife-to-be—and possibly having him followed to make sure he obeyed. In a step that may have been rather cunning, she moved with her son around 1942 to a farm in Bucks County, Pennsylvania, where their neighbors included Oscar Hammerstein, Jr. With composer Jerome Kern, lyricist Hammerstein had written the songs for the watershed 1927 musical Showboat, and was about to form his partnership with composer Richard Rodgers and in 1943 advance the Broadway musical yet again, with Oklahoma!
Young Stephen Sondheim befriended Oscar’s son, Jamie, and became a fixture at the Hammerstein house. In the famous lyricist he found not only a surrogate father but a vision of the future. For his part, Hammerstein had an immense trove of technical knowledge to share, and arranged a summer job for the teenage Sondheim as a gofer on the set of Rodgers and Hammerstein’s Allegro.