It made him a popular phenomenon, the first real teen idol, with school girls swooning in the aisles. His big breakthrough came due to his engagement as a support act to Benny Goodman at the Paramount Theatre in New York, which began on New Year's Eve. The recording ban called by the American Federation of Musicians, which had begun the previous month, initially prevented him from making records, but he appeared on a 15-minute radio series, Songs By Sinatra, from October through the end of the year and also did a few live dates. Sinatra left the Dorsey band in September 1942. In January 1942, he tested the waters for a solo career by recording a four-song session arranged and conducted by Axel Stordahl that included Cole Porter's "Night and Day," which became his first chart entry under his own name in March 1942. During this period, he also performed on various radio shows with Dorsey and appeared with the band in the films Las Vegas Nights (1941) and Ship Ahoy (1942). Over the next two and a half years, he was featured on 16 Top Ten hits recorded by Dorsey, among them the chart-topper "I'll Never Smile Again," later inducted into the Grammy Hall of Fame. At the end of the year, Sinatra accepted an offer from the far more successful bandleader Tommy Dorsey, jumping to his new berth in January 1940. 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.
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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.
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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.
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In a professional career that lasted 60 years, he demonstrated a remarkable ability to maintain his appeal and pursue his musical goals despite often countervailing trends. Frank Sinatra was arguably the most important popular music figure of the 20th century, his only real rivals for the title being Bing Crosby, Elvis Presley, and the Beatles.