Gilbert began his career performing stage musicals with his parents during the 1920s, though after his father’s death he and his mother found work as extras. It was while on set that Gilbert was able to work his way up and become an assistant director, learning directing cues from Alfred Hitchcock and other noted directors. At the onset of World War II, Gilbert joined the British Royal Air Force’s film unit, keeping a filmed record of the British military.
Following the war, Gilbert helmed his first project, a documentary short entitled, The Ten Year Plan (1945). He continued working steadily in the British film industry, producing several hits, including Alfie, for which he received an Academy Award nomination for Best Film. Gilbert has been nominated for four BAFTA Awards, winning Best Film for Educating Rita (1983).
Gilbert joined the Directors Guild in 1979 and has been nominated for two DGA Awards for Outstanding Directorial Achievement in Motion Pictures, for Alfie and Sink the Bismarck!