Benny Kubelsky was reared in Waukegan, a small city north of Chicago, where his father operated a saloon and later a dry goods store. As a boy he helped out in the store and took up the violin, and by his high school years had become proficient with the instrument. He played it in vaudeville from 1912, and in 1918 when he was taken into the U.S. Navy he was assigned to entertainment duties. It was there that his comic talent came to light and, while he remained a competent violinist in private, on stage his violin soon became little more than a prop which he played ineptly for comic effect.

Audiences responded to Benny's type of humour. In an era of comedy characterized by broad jokes and rapid delivery, his style was subtle and languid. Over the years, he and his cast—including Eddie Anderson as Rochester, his chauffeur and valet; and Benny's wife, Sadie Marks, as Mary Livingstone, his nemesis—carefully developed his stage image as a vain, stingy man and would-be violinist. He was notable for his verbal inflection and his acute sense of timing.

“The Jack Benny Program” remained on network radio for 23 years, at which time Benny moved to television, where he appeared regularly until 1965.