Sinatra decided to become a singer after watching Bing Crosby perform in the mid 1930s. In 1940, Tommy Dorsey asked Sinatra to join his band, which jump started Sinatra's career. After experiencing two years of success, Sinatra decided to go solo before the war started.
During war time, Sinatra was unable to serve in the military due to a ruptured eardrum. He is quoted as saying "It was the war years, and there was a great loneliness, I was the boy in every corner drugstore who'd gone off, drafted to the war. That was all." So, he began his acting career and soon began to earn awards for his performances. However, he never gave up his music.
In the 1960s, Sinatra turned to Las Vegas as a founding member of the "Rat Pack". Much of his creative process during this time was collaboration with the other members of the band. When he was a solo artist, he worked mostly by insight. He would spend many in the studio and wouldn't leave until he achieved his desire result.
While Sinatra was and continues to be beloved, he had a reputation that preceded him. He was regarded as very moody. One day he would be gentle and philanthropic, the next he could be extremely demanding. He was extremely arrogant and didn't do well with incessant media attention. Nevertheless, the music he created is universally respected and withstands the test of time.
https://www.biography.com/musician/frank-sinatra
https://www.nypl.org/events/exhibitions/sinatra-american-icon/more
I love that you brought up Bing Crosby's influence on Sinatra. Sinatra idolized Crosby and eventually got to star in two films with him. Sinatra at first may have learned from Crosby's singing and even tried to copy his style. But once Sinatra decided to branch out beyond the Crosby classics, that's when his talent flourished. It goes to show the importance of a mentor but the need to break free from a mentor in order to become a creative
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