After graduating from UMass Lowell with performance degrees in piano and trombone, Roy toured as principal trombonist with Milton Berle in a two-year vaudeville review. Returning to Boston, he worked as trombonist with Sarah Caldwell's "Boston Opera Company" and as house trombonist for the Colonial Theater, South Shore Music Circus, and the Cape Cod Melody Tent. Roy has also performed at the Shubert and Wang Theaters and with the Boston Pops "Adventures In Music" concerts.
Roy has taught at Brown University, Norwood High School, and South Shore Conservatory. He is currently professor of music at Bridgewater State University. He has directed shows at Monomoy Theater in Chatham, Harwich Jr. Theater, and was conductor and director of bands at Bridgewater State University.