James hired Sinatra, and the new singer made his first recordings on July 13, 1939. He was still singing there in the spring of 1939, when he was heard over the radio by trumpeter Harry James, who had recently organized his own big band after leaving Benny Goodman. Sinatra then took a job as a singing waiter and MC at the Rustic Cabin in Englewood, NJ. The group won the radio show contest and toured with Bowes. In September 1935, he appeared as part of the vocal group the Hoboken Four on Major Bowes' Original Amateur Hour. The son of a fireman, Sinatra dropped out of high school in his senior year to pursue a career in music. On records and in live performances, on film, radio, and television, he consistently sang standards in a way that demonstrated their perennial appeal. He was able to take the work of great theater composers of that period, such as Jerome Kern, Irving Berlin, George Gershwin, Cole Porter, and Richard Rodgers, and reinterpret their songs for later audiences in a way that led to their rediscovery and their permanent enshrinement as classics. This popularity was a mark of his success at singing and promoting the American popular song as it was written, particularly in the 1920s, '30s, and '40s. He scored his first number one hit in 1940 and was still making million-selling recordings in 1994. He came to the fore during the swing era of the 1930s and '40s, helped to define the "sing era" of the '40s and '50s, and continued to attract listeners during the rock era that began in the mid-'50s. In a professional career lasting 60 years, he demonstrated a remarkable ability to maintain his appeal and pursue his musical goals despite countervailing trends. Frank Sinatra was arguably the most important musical figure of the 20th century, his only real rivals for the title being Elvis Presley and the Beatles.
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