Initially, Gielgud agreed only to direct the play, but Whitehead persuaded him to take on the role of Jason.Gielgud also played Raskolnikov in Crime and Punishment, Whitehead's next production, which co-starred Lillian Gish and Dolly Haas and which, like Medea, was a box-office hit to the surprise of some. "Broadway has the idea," said Whitehead in 1950, "that things are either commercial or art. I have never seen a really artistic play that failed, unless it was badly done."His production of Carson McCullers's Member of the Wedding (1950), directed by Clurman, won the Critics' Circle Award and was later filmed with the same three leading players. Whitehead had cast the little-known Julie Harris, then 24 years old, as the sensitive 12-year-old heroine who feels abandoned as her beloved older brother prepares for his wedding.To fill the role of the family's black housekeeper who comforts the troubled youngster, Whitehead ventured to a second-rate night-club in Detroit to sign the blues singer Ethel Waters, whose career was at a low ebb. The script called for her to sing a Russian lullaby at one point, but Whitehead agreed to her request that she sing instead a favourite spiritual, "His Eye is on the Sparrow".

It was to become a highlight of the play and film, and later became the title of Waters's autobiography.Whitehead and Clurman's other collaborations included O'Neill's Desire Under the Elms, Laurents's The Time of the Cuckoo (both 1952), Inge's Bus Stop (1955), Anouilh's Waltz of the Toreadors (1957) and Williams's Orpheus Descending (1957).When Whitehead took Terence Rattigan's London hit Separate Tables to Broadway in 1956 the playwright wrote him an impassioned letter asking that he be allowed to make changes to the play. The strict censorship of the London theatre by the Lord Chamberlain had made it impossible for the character of "The Major" to be a homosexual instead of a molester of women, something Rattigan hoped to rectify, but Whitehead was horrified, stating that homosexuality "has become almost a clich?n the American stage". He argued that the play's message of tolerance would be diluted by being so specific "I feel the play becomes smaller," he wrote. "It becomes a play about homosexuality, which it isn't." Though Rattigan was disappointed, Whitehead's judgement proved sound when the play won rave reviews and ran for nearly a year.In 1958 Whitehead produced his first musical, Goldilocks, which was troubled from the start when the leading man Ben Gazzara, who could not sing, was replaced by Barry Sullivan, who also could not sing. Sullivan was replaced by Don Ameche, who could sing but who had no rapport with the leading lady. The columnist Walter Winchell wrote, "Elaine Stritch and Don Ameche, who make all that love on stage at Goldilocks, practically have to be introduced after the asbestos falls."Whitehead had little success with other musicals, The Conquering Hero (1961), Foxy (1962) and 1600 Pennsylvania Avenue (1976), but he won his fifth Critics' Circle Award with Robert Bolt's play A Man for All Seasons (1961), which also won the Tony Award as Best Play.In 1964 the Lincoln Center Repertory Theatre opened with Robert Whitehead and Elia Kazan as its heads and Harold Clurman as literary adviser. Their first play was Arthur Miller's After the Fall, based on his marriage to Marilyn Monroe, but it was not well received.

When four subsequent productions fared badly, Whitehead and Kazan were relieved of their posts at the end of the season. It was something Whitehead would not speak of publicly, but he was back on Broadway in 1968 with The Prime of Miss Jean Brodie. Katharine Hepburn starred in two Whitehead productions, A Matter of Gravity (1976) and West Side Waltz (1981), and he continued his association with Arthur Miller by producing The Price (1968), The Creation of the World and Other Business (1972), a revival of Death of a Salesman (1984) with Dustin Hoffman, and Broken Glass (1994). He was one of the producers of two Pinter plays, No Man's Land with Gielgud and Richardson, and Betrayal, plus Tom Stoppard's Artist Descending a Staircase.In 1968 Whitehead married Zoe Caldwell, who starred in The Prime of Miss Jean Brodie.