Harry Roy is best remembered for having led a popular swing band in England and throughout portions of the British Empire during the 1930s. Roy was born Harry Lipman in London, England, on January 12, 1900, and as a teenager he worked in his father's carton manufactory, studying various musical instruments during his free time. In 1919, when the Original Dixieland Jazz Band wowed the crowds in London, young Harry was dazzled by Larry Shields and took up the clarinet. In 1921, he formed a band with his brother, pianist Syd Lipman. They called their group the Darmswells, but when the O.D.J.B. ended their run at the Hammersmith Palais de Danse the Roy Brothers Original Lyrical Five took their place. This was a variation on yet another of their various titles, the Original Crichton Lyrical Orchestra. The now Anglicized "Roys" waxed a test pressing for Columbia in 1922 and made their first issued recordings for Vocalion in 1927 as the Crichton Lyricals. Over the next few years their music became available to the public on the Guardsman, Coliseum, Aco, Scala, Crown, Beltona, Imperial, and Crystalate record labels. The Lyricals played all of the best halls and clubs in London, visited Paris, then toured Australia, Tasmania, and South Africa in 1928. They cut two sides for the Broadcast label in 1929 and visited Berlin in 1930, providing live entertainment and making a few more phonograph records. Harry was a born showman, comedian, and vocalist who specialized in songs like "I Wonder How I Look When I'm Asleep?"
Harry became the leader of a new enlarged version of the band in 1931, with Syd assuming managerial duties. The Harry Roy Orchestra spent half a year serenading patrons before and betwixt motion picture screenings at RKO's Leicester Square Theatre, opened at the London Pavillion in 1932, and broadcast over BBC radio from the Café Anglais in 1933. Their theme song was now established as the "Bugle Call Rag." Roy's band distinguished itself at the Mayfair Hotel in 1934 and remained there until 1936. In 1935, Harry married "Princess Pearl" Eliza Vyner Brooke, daughter of Charles Vyner Brooke, the last white Rajah of the state of Sarawak in Northwestern Borneo. The Harry Roy Orchestra even appeared in motion pictures: "Everything in Heaven" was released in 1935, starring vocalists Princess Pearl and Mabel Mercer, and "Rhythm Racketeers" followed in 1936.
Harry Roy's Orchestra enjoyed a successful tour of South America in 1938 and toured consistently throughout England and the Middle East during the Second World War, after which Roy attempted to perform in the United States of America but was unable to obtain a work permit. His band resumed playing the Café Anglais in 1949. Soon afterward he dissolved his band and opened a restaurant. His last-known public appearance was with a quartet in 1969. Roy fell ill and passed away in London on February 2, 1971.