Caine was the son of British novelist Hall Caine and his wife Mary Chandler. He was born at Keswick in Cumberland, and so derived his name from the nearby lake of Derwent Water. He was a sensitive child with asthma, and attended St Cyprian's School in Eastbourne for his health. He became an actor, making his stage debut in 1906 in his father's adaptation of his novel, The Bondman. His father went to America to encourage American involvement in World War I and had dramatic interests there. In 1915, Derwent Caine sailed to America to look after those interests. Although he was declared unfit for active service, he was nearly prevented from travelling because of a change of rules. In America, he starred in three films made by the Arrow Film Corporation. These were The Deemster, a version of Crime and Punishment by Dostoyevsky, and the propaganda film Huns Within Our Gates. Back in England, with his brother Gordon Ralph Hall Caine, he founded the publishing house The Reader's Library. In 1929, he stood for parliament as Labour candidate for Liverpool, Everton and was returned as Member of Parliament. In January 1931, he was charged with dangerous driving after colliding with a taxi in the early hours of the morning in Trafalgar Square, injuring the four taxi passengers. Caine was subsequently acquitted. When the Labour government collapsed in 1931, he carried on supporting Ramsay MacDonald as a National Labour MP. Hall Caine was the only sitting National Labour MP to be opposed by the Conservatives in the 1931 General Election. He lost his seat to Frank Hornby, and finished bottom of the poll. At the same election, his elder brother Gordon Hall Caine was elected Conservative member for East Dorset. He was given a knighthood in 1935 and a baronetcy in 1937. Caine had at least three children out of wedlock, and one of them, Elin, was adopted by Caine's parents as their own daughter in 1912. He died in Miami.
In 1935, Gordon Hall Caine and Derwent Hall Caine established the Hall Caine Airport on the Isle of Man. Both Sir Thomas Henry Hall Caine's sons were particularly keen on the development of an aerodrome in the north of the Isle of Man, as they saw it as another bit of the Island as being associated with their late father. They were said to be extremely interested in the progress of the Isle of Man and in particular its transport infrastructure. They also wished to include Ramsey'smunicipal authority in the project, as they were both of the opinion that the aerodrome would bring immense benefit to the town. Amongst the ambitious plans envisaged by Derwent Hall Caine was the inclusion of the airfield as part of an air network running the length of the country from Jersey and staging through numerous destinations including Hall Caine Airport, terminating at Campbeltown. In an interview with the Ramsey Courier Derwent Hall Caine stated that from the introduction of air services, the site was to be known as Hall Caine Manx Airport. This was subsequently changed to the Hall Caine Airport, Ramsey. With all parties duly satisfied, Hall Caine Airport officially came into being on 30 April 1935. Hall Caine Airport flourished from 1935 until it ceased commercial operations in 1937.
