Gentry learned to play clarinet while growing up in Sterling, Colorado, and attended Colorado State Teachers College before moving to Los Angeles to pursue a career in music. He played with Vido Musso in 1939, then with Harry James in 1940-41; during World War II he worked with Benny Goodman, the Army band of Glenn Miller, and Artie Shaw. He then worked with Jan Savitt before returning to Goodman's employ in 1946. After 1947 he worked often as a session musician with, among others, Louis Armstrong, Georgie Auld, Charlie Barnet, Ralph Burns, Benny Carter, June Christy, Sammy Davis Jr., Ella Fitzgerald, Pete Fountain, The Four Freshmen, Erroll Garner, Woody Herman, Stan Kenton, Spud Murphy, Anita O'Day, Patti Page, Mel Powell, Della Reese, Shorty Rogers, Pete Rugolo, Mel Torme, and Nancy Wilson.
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With Benny Carter
- Aspects (United Artists, 1959)