Larry Kert had been on Broadway for seven years before he was tapped to play the role of Tony in Bernstein and Sondheim musical, West Side Story. Previously, he had debuted in 1950 as a member of the Upstarts, a troupe featured in the musical revue, Tickets, Please! He later appeared in another Broadway revue, John Murray Anderson’s Almanac (1953–54), in a cast that also featured Harry Belafonte, Polly Bergen, Hermione Gingold, Orson Bean, and Tina Louise. It was as a replacement dancer in Mr. Wonderful that Kert was spotted for West Side Story. Kert was considered too old in 1960 to play Tony in the film version of the musical.
After West Side Story, Kert appeared in a short-lived musical, A Family Affair (1962), by John Kander and William Goldman as well as in the ill-fated musical adaptation of Truman Capote’s Breakfast at Tiffany’s from 1969, which never actually opened. His next Broadway appearance, in La Strada, Lionel Bart’s musical adaptation of Federico Fellini’s film, fared little better: The show closed opening night.
Kert, though he was Dean Jones’s replacement, earned his first and only Tony® nomination in 1971 for Best Actor in a Musical with his portrayal of Robert in Stephen Sondheim’s Company. The Original Broadway Cast recording was made with Jones; Columbia subsequently made a London Cast recording, with Kert as Robert.