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going off the options there - the 1940's by far, even if Sinatra did not really start to reach his peak musically until the early 1950's.
But I am huge fan of jazz/swing (and ragtime as well), so there is strong bias there personally. The 1940's also saw some of the greatest radio shows, or shows at their prime before Television became such a driving force in the 50's and later.
and if anyone is curious, I was born in '77.
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