Ironically Crosby is considered the first modern pop star because of his vocalese. He moved closer into the mike to sing casually, essentially 'croon'.
Prior that Al Jolson, Rudy Valle, blues and jazz singers sang louder(a greater distance from the mike) and much more mannered.
Crosby's classic 40's and 50's sides stand up, they are solid. He just isn't fashionable (for a lot of reasons).
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