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?"