Jim Dale began his career as a stand-up comic. He sharpened his comedy skills during a stint in the army, where he organized and performed in camp shows. After his discharge he pursued a comedy career, and landed a job as the warm-up comic on a musical variety show. He did so well that the producers gave him a spot on the show as a singer, and he quickly became a recording star. He was signed for a small part in one of the "Carry On" films, Carry on Cabby (1963), but the audience reaction to him was so great that he was soon made a regular member of the cast. Unlike many comics, Dale insisted on performing his own stunts, and in fact injured his arm performing a stunt in Carry on Again Doctor (1969), his last film of the series until 1992.

After his departure from the series he returned to the stage, notably in Sir Laurence Olivier's National Theater. In the 1970s Dale moved to the US for film and stage work, achieving success in the Broadway show "Barnum" and in a string of film comedies for Disney.

He returned to Britain in 1992 for an appearance in the final "Carry On" film, Carry on Columbus (1992).