Technically "eldest," John was born half an hour before Roy; both twins debuted in Anthony Asquith's 1931 film Tell England at eighteen while still attending the Reading School in Berkshire. John worked as an ambulance driver in the Spanish Civil War for most of 1937. After his return, the brothers established Charter Film Productions and began making shorts. Boultings came to prominence in 1940 with Pastor Hall, Martin Niemöller's anti-nazi biopic based on Ernst Toller's eponymous play. Produced by John and directed by Roy, it was a critical and commercial breakthrough for aspiring brothers; James Roosevelt distributed the film in North America via [url=https://discogs.com/label/296259]United Artists[/url], where it screened with Eleanor Roosevelt's prologue. During the Second World War, John served as the Royal Air Force lieutenant, soon joining RAF's Film Unit Production, where he created Journey Together in 1945, a dramatized documentary co-written by Terence Rattigan and starring Richard Attenborough.

The brothers periodically switched roles; for instance, John directed Brighton Rock crime drama in 1946, which became a notable box office attraction and caused uproar for its explicit depiction of violence, or The Magic Box (1951), marked by multiple cameos. John and Roy co-produced and co-directed several movies, including Seven Days to Noon thriller, which earned Boultings the Golden Lion nomination at the 1950 Venice Film Festival, or the WWII naval epic Seagulls over Sorrento (1954) on [url=https://discogs.com/label/154276]MGM[/url] starring Gene Kelly. They filmed a series of critically acclaimed satirical comedies between 1956 and 1959, led by a star cast of Richard Attenborough, Terry-Thomas, [url=https://discogs.com/artist/791410]Ian Carmichael[/url], and Peter Sellers.

John's last work as a director was a mildly successful heist comedy, Rotten to the Core, in 1965, co-written and produced by Roy. The following year, John produced a critically and financially successful northern comedy, The Family Way, directed by Roy and featuring Paul McCartney's soundtrack. The Boulting Brothers' career went into decline afterward, only worsened by a few controversies involving Roy; the 1970 romantic comedy There's a Girl in My Soup with Sellers and Goldie Hawn, directed by Roy and co-produced by John with M. J. Frankovich, became their last notable success. (A few songs from the film by Mike D'Abo, including "Miss Me In The Morning," briefly charted in Europe.)

In 1974, John co-produced Roy's comedy Soft Beds, Hard Battles, which became a massive commercial flop despite a prominent cast with Peter Sellers, Curd Jürgens, Lila Kedrova, and Jenny Hanley. It was John's last job in cinema; Roy's final comedy, The Last Word (1979), saw only limited release and performed even worse in the UK's box office. In 1985, seventy-two-year-old John died of cancer; Roy Boulting stopped making films afterward but outlived his brother by 16 years.