On January 26, 1940, Sinatra made his first public appearance with the Dorsey band at the Coronado Theater in Rockford, Illinois.
In his first year with Dorsey, Sinatra released more than forty songs, with "I'll Never Smile Again" topping the charts for twelve weeks beginning in mid-July.
Sinatra's relationship with Tommy Dorsey was troubled, because of their contract, which awarded Dorsey one-third of Sinatra's lifetime earnings in the entertainment industry. In January 1942, Sinatra recorded his first solo sessions without the Dorsey band (but with Dorsey's arranger Axel Stordahl and with Dorsey's approval). These sessions were released commercially on the Bluebird label. Sinatra left the Dorsey band late in 1942 in an incident that started rumors of Sinatra's involvement with the Mafia. A story appeared in the Hearst newspapers that mobster Sam Giancana coerced Dorsey to let Sinatra out of his contract for a few thousand dollars, and was fictionalized in the movie The Godfather. According to Nancy Sinatra's biography, the Hearst rumors were started because of Frank's Democratic politics. In fact, the contract was bought out by MCA founder Jules Stein for $75,000.
(extract from Wikipedia 2011)
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