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Born in Richmond, Surrey, England, Denny (sources differ on his birth name giving variously Reginald Daymore, Reginald Leigh Daymore and Reginald Leigh Dugmore Denny, but he is listed in birth records as Reginald Leigh Dugmore) began his stage career at age seven in The Royal Family. At age 16, he appeared in The Merry Widow. That year he left the Jesuit school which he had been attending, St Francis Xavier College, Mayfield, Sussex. Years later he joined an opera company as a baritone, and toured India.
He came from a theatrical family that went to the United States in 1912 to appear in the stage production Quaker Girl. His father was the actor and singer W.H. Denny. After continuing his stage career in the United States, Reginald began his film career in 1915 with the World Film Company and made films both in the United States and Britain until the 1960s. Reginald appeared in John Barrymore's 1920 Broadway production of Richard III; the two actors became friends.
In the 1920s he performed as a stunt pilot and in the early 1930s, Denny became interested in radio controlled modelaeroplanes. He and his business partners formed Reginald Denny Industries and opened a model plane shop in 1934, which became a chain known as the Reginald Denny Hobby Shops.
Denny bought a plane design from Walter Righter in 1938 and began marketing it as the "Dennyplane", and a model engine called the "Dennymite". In 1940, Denny and his partners won a US Army contract for their radio-controlled target drone, the OQ-2 Radioplane. They manufactured nearly fifteen thousand drones for the US Army during the Second World War. The company was purchased by Northrop in 1952.
Marilyn Monroe was discovered working as an assembler at Radioplane. A photographer assigned by Denny's friend, Army publicist (and future US President) Captain Ronald Reagan, took several shots and persuaded her to work as a model, which was the beginning of her career.
Denny married actress Irene Hilda Haismann on 28 Jan 1913 in Calcutta, both were with the Baudmann Opera Company. They had one daughter but were divorced in 1928.
Denny married Betsy Lee in 1928 and they had three children. Denny died on 18 June 1967 aged 75 while visiting his sister in Richmond. Betsy died in 1996 aged 89.