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Frank Sinatra went against American mainstream values in the 1950's. He was a swinging bachelor, a flashy dresser, and a "tender tough guy", who became a male role model for many emotionally scarred WWII veterans (who had rejected him in the 1940's because he did not pass the physical when drafted). Many of these veterans came back from WWII and did not fit into mainstream American society. A few of these men became Hell's Angels, and some of them adopted the defiant, dangerous to mainstream values, swaggering yet sensitive persona of people such as James Dean, Montgomery Clift, the young Marlon Brando, and Frank Sinatra. There was a "generation gap" in the 1950's, and for teenagers, Elvis and James Dean personified "cool." For a great many adults, Frank Sinatra was the epitome of "cool." Sinatra's music addressed the romantic yearning, loneliness and isolation, and adult concerns of people in their 20's through 40's.

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Q: Why was Frank Sinatra important to the 1950's?
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