His first film was an uncredited appearance in the 1954 The Men of Sherwood Forest and several more similar roles followed until in 1959 when he secured his first substantial part in Too Many Crooks. All the while, he continued to appear on stage, mainly in Shakespearean roles and in a variety of UK TV parts, including roles in "Meet The Champ", "Our House", "Z-Cars" (this episode is lost) and "Dangerman" (starring Patrick McGoohan).
It was not until 1965 when he got his big film break, being cast as "Little Heap" in "Carry On Cowboy".
Indeed, while versatile, he is best remembered for his comedy work as a near-constant member of the "Carry On" team, making 14 films with them and at 6' 7" tall he was, by far, the tallest member of the "Carry On" cast.
Bresslaw was married to dancer Betty Wright from 1959 until his death, of a sudden heart attack in his dressing room at the Open Air Theatre in Regents Park, London, where he was to play Grumio in the New Shakespeare Company's production of Taming of the Shrew. He was cremated at Golders Green Crematorium, where his ashes were buried.