Roy Boulting began working in film sales around 1933, subsequently moving to production. He served as an assistant director on the 1936 short comedy Apron Fools. John and Roy established their Charter Film Productions company and began directing and filming shorts. A few of their works, such as The Landlady (1937) and Consider Your Verdict (1938), soon gained critical and commercial acclaim. Roy directed his first feature-length Hollywood movie after the Second World War, the Sailor of the King, for [l=20th Century Fox], starring Jeffrey Hunter, Jr. in 1953. Their second WWII naval war epic, this time for [l=Metro-Goldwyn-Mayer], Seagulls over Sorrento, featuring Gene Kelly in 1954, had less prominence.

In the following decade, Boultings primarily focused on satire to highlight various British societal issues, from academia and corrupted unions to government bureaucracy or the inefficient legal system. The series began with John's look on military life, Private's Progress in 1956, starring Richard Attenborough, Terry-Thomas, and [url=https://discogs.com/artist/791410]Ian Carmichael[/url]; it became the second biggest box office hit in the UK that year. The Lucky Jim followed in 1957, adapted from an eponymous novel by Kingsley Amis and set in academia. In 1966, the brothers directed and produced The Family Way, a northern comedy with Paul McCartney's soundtrack starring [url=https://discogs.com/artist/1390467]John Mills[/url] and his teenage daughter Hayley Mills. Roy Boulting and Hayley had a 33-year age difference but began a relationship during the shoot; they married in 1971. (In 1987, The Smiths used The Family Way's still-frame as a cover for I Started Something I Couldn't Finish single.)