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Frank Sinatra & Tommy Dorsey

At the end of 1939, Frank Sinatra left the Harry James Orchestra to join the Tommy Dorsey Orchestra, where he rose to fame as a ballad singer. His first and biggest hit with the band was 1940s "I'll Never Smile Again," which spent several weeks at number one - and was the first "number one" - on Billboard magazine's then-new chart of America's top-selling records. His vast appeal to the "bobby soxers," as teenage girls were called, revealed a whole new audience for popular music, which had appealed mainly to adults up to that time. (The complete span of his career with Dorsey was released in the 1994 box set The Song Is You.)

From March 13 to April 9, 1940 Sinatra sang with the Tommy Dorsey Band at the New York Paramount, the venue in which he, as a solo singer, caused pandemonium during the coming years. On record, Sinatra cut 29 singles with Dorsey during 1941 and was named Male Vocalist of the Year by Billboard that May. His departure from the Tommy Dorsey Orchestra was announced on stage at the Circle Theatre in Indianapolis on August 28, 1942 User-contributed text is available under the Creative Commons By-SA License; additional terms may apply.