An article here tries to reach some conclusions abut the reasons for the popularity of certain artists to certain generations in each decade, Bing for the 1940s, under the title "What Every Generation's Favorite Artist Says About Them".

http://www.policymic.com/articles/85555/what-every-generation-s-favorite-artist-says-about-them

I don't think it reaches any startling or new conclusions but along the way it does make some odd statements. Among them there is  "Crooning, a gentle kind of singing, became popular in the '20s and '30s because singing loudly would blow early radio tubes". Really? Were "loud" singers not broadcasting in those days? Total nonsense. If there were any danger of overloading the equipment the microphone feed was turned down, or the singer took step back. "Crooning" developed because microphones and amplification allowed a softer, more intimate singing style to reach the audience. It was a development initiated by the singer (notably Bing), not one enforced by necessity through the limitations of the equipment. And Bing could be "loud" as they crudely describe it. Listen to "High Water" and others. Not all Bing's singing could even remotely be described as "crooning". 

And then "Bing Crosby perfected the style and his music was about as inoffensive and soft as is possible". Well yes, he perfected the style - but "soft as possible"? Have they not heard any of Bing's up tempo numbers, his rousing sessions with, for example Johnny Mercer and Connee Boswell, not to mention numbers with some of the big bands. Bing was hardly a whispering Jack Smith. I don't know what to make of the "inoffensive" bit. I don't think popular musicians tried to be offensive until somewhere around the seventies with groups like the Sex Pistols and other punk rockers. They might take new initiatives and try to innovate, not to offend, but why is that portrayed as a negative?