“On Friday nights I could do two Jewish services at different temples,” he said in an interview for “The School of Doing: Lessons From Theater Master Gerald Freedman,” a 2017 book by Isaac Klein. “On Saturday morning, I could do another Jewish service. On Sunday, I could do usually two churches. An early Mass, Presbyterian or Episcopalian, and in late afternoon there would be another Mass. And with five services, I could live off that for the next week.”
He was hired to design and paint scenery at a summer stock company in Massachusetts and then, in 1952, to direct “As You Like It” at Equity Library Theater in New York. Someone from Columbia Pictures saw it and gave him a contract that took him to Hollywood, where one of his first assignments was as dialogue director on “It Should Happen to You,” a George Cukor movie starring Judy Holliday.
She became a friend. In 1956, when Ms. Holliday was hired for the musical “Bells Are Ringing” on Broadway, Jerome Robbins, the director, who Mr. Freedman said was intimidated by the star, hired him to assist on the production.
“It was either to placate Judy or as insurance,” Mr. Freedman said. “I never knew which.”
The partnership was Mr. Freedman’s big break. He was Mr. Robbins’s assistant again the next year on “West Side Story,” and in 1959 on “Gypsy.” He also served as a buffer between the actors and Mr. Robbins, who could be abrasive.
“I went around repairing Jerry’s damage with actors,” Mr. Freedman was quoted as saying in “Dancing With Demons: The Life of Jerome Robbins” (2001), by Greg Lawrence. “I don’t mean that in a negative way. It was just because he didn’t know how to talk with them.”
By 1960, Mr. Freedman was working with Mr. Papp. He directed a well-received “The Taming of the Shrew” that year for the New York Shakespeare Festival in Central Park.
In 1964, Mr. Papp named Mr. Freedman artistic director of the Shakespeare Festival and announced his intention to include contemporary fare. One result was the rock musical “Hair,” with a book by Gerome Ragni and James Rado and music by Galt MacDermot. Mr. Freedman was assigned to direct the premiere, which was to open in Mr. Papp’s new space on Lafayette Street in Manhattan. It was a rocky trip to opening night.