reach for the sky phrase. Reach for the Sky is a 1956 British biographical film about aviator Douglas Bader, based on the 1954 biography of the same name by Paul Brickhill.The film stars Kenneth More and was directed by Lewis Gilbert.It won the BAFTA Award for Best British Film of 1956. Directed by Lewis Gilbert. With Kenneth More, Muriel Pavlow, Lyndon Brook, Lee Patterson. What does reach for the sky expression mean? Definitions by the largest Idiom Dictionary. The film's composer John Addison was Bader's brother-in-law. Definition of reach for the sky in the Idioms Dictionary. Biopic of RAF Group Captain Douglas Bader who, after having lost both legs, flew a British fighter plane during WW2.