As a boy, he started singing and entertaining, but his family disapproved of his interest in the music hall and he was sent to Canada to live with relatives.

He took the stage name Issy Bonn at the suggestion of BBC Radio producer John Sharman, who produced a popular programme, John Sharman's Music Hall,[3] and made his first radio appearance on the show in 1935, billed as "The Hebrew Vocal Raconteur".

[3][5] Issy Bonn made over a thousand radio broadcasts on programmes such as Variety Bandbox,[4] and reputedly had a repertoire of over 500 songs.

He toured Europe with the Entertainments National Service Association (ENSA), and after the Second World War wrote and starred in his own road shows including The Big Broadcasts and The Melody Lingers On.

[2][5] In the 1950s, his style of humour, trading on traditional Jewish stereotypes,[7] went out of fashion, but he continued to appear on radio, television, and in pantomimes, and toured, often with the popular trumpeter Eddie Calvert.