Early Life
May was born in Pittsburgh, Pennsylvania. He started out playing the tuba in the high school band. "I sat in the rear of the stand. I didn't realize it at the time, but I was intrigued with becoming an arranger and an orchestrator." At the age of seventeen May began playing with Gene Olsen's Polish-American Orchestra. After playing for a few local bands, May heard Charlie Barnet's band on the radio in his hometown of Pittsburgh. May approached the bandleader and asked if he could write arrangements for the band. This happened in the summer of 1938. From 1938 to 1940, May wrote arrangements and played trumpet for Charlie Barnet's big band. His arrangement of the Ray Noble composition "Cherokee" became a major hit of the swing music era. During the Barnet days, May revealed a significant flair for satire on a composition titled "The Wrong Idea", composed with Charlie Barnet, that ridiculed the bland "Mickey Mouse" style of safe big-band music with specific musical mockery of bandleader Sammy Kaye, known for his "swing and sway" trademark. May's caustic lyrics to the song called it "swing and sweat with Charlie Barnet". Bandleader Glenn Miller hired May away from Charlie Barnet in 1940. "May points out that he was not responsible for any of the band's signature hits, but he did write the beautiful left-field introduction to Finegan's 'Serenade In Blue'."
May worked as an arranger for the bands of Glenn Miller and Les Brown before being hired as staff arranger first for the NBC radio network, then for Capitol Records.
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