Ross was born on May 13, 1927 in Brooklyn, New York, the son of Martha Grundfast and Louis Chester Ross, a postal clerk. At the age of 9, his mother died and his father moved the family to Miami and opened a luncheonette.
In 1942, Ross' stage debut came as "Third Witch" in a touring company of Macbeth. The next year brought his first Broadway performance credits with Something for the Boys. By 1950, he was a choreographer with the American Ballet Theatre and choreographed his first Broadway production, the Arthur Schwartz-Dorothy Fields musical adaptation of A Tree Grows in Brooklyn.
Ross's first film assignment came as an uncredited choreographer on Carmen Jones (1954). In the UK, he choreographed The Young Ones (1961) and Summer Holiday (1963), both starring Cliff Richard. Later, he worked with Barbra Streisand as choreographer and director of musical numbers for Funny Girl (1968).
His film directorial debut came with the musical version of Goodbye, Mr. Chips (1969), made by MGM-British, with Peter O'Toole and Petula Clark. He went on to direct films involving ballet, such as The Turning Point (1977), Nijinsky (1980) and Dancers (1987). Other movies of critical acclaim followed in the 1970s and 1980s such as Neil Simon's adaptations of his own plays and film adaptations of Broadway productions through his last project, Boys on the Side (1995).
In 1959, he married Nora Kaye, a ballerina, with whom he produced four films. In 1987, when Ross was 60, he was widowed as his wife Nora succumbed to cancer.
In September 1988, he married for the second time to Lee Bouvier Radziwill , the younger sister of Jacqueline Bouvier Onassis. The marriage ended in divorce in 2001, shortly before his death. In 2013, Lee described their relationship as follows:
“He was certainly different from anybody else I’d been involved with, and the film world sounded exciting. Well, it wasn’t. I hated Hollywood, and the provincialism of the industry... Herbert had been married to the ballerina Nora Kaye until she died, and unbeknownst to me was still obsessed by her. It was ‘Nora said this, Nora did it like that, Nora liked brown and orange.”
On October 9, 2001, Ross died from heart failure in New York City. A memorial was held for him at the Majestic Theater on West 44th Street in New York where Leslie Browne, Barbara Cook, Arthur Laurents, Marsha Mason, Mike Nichols and Mary-Louise Parker spoke of Ross. He was interred with Kaye in the Westwood Village Memorial Park Cemetery in Los Angeles.