I picked the 1940s. Bing's voice sounded tired at times, but I am going through a WWII phase and after reading Gary Giddins' book, it put me more in the mood for this era.

Ron1972 wrote:

I chose the 50's because despite Crosby thinking his abilities were diminishing, THIS is the sound when I think of Bing Crosby, smooth and seemingly effortless!

I love the sound of Crosby on the different albums from the decade, whether it's a little dixieland with Scoby, brash with Bregman, or duetting with Clooney. 

And then there is all the tracks recorded for his radio show, not quite part of his recording career, (tho some were used by Decca),. They just impress me with every listen and I alternate from liking Bing with full sounding arrangements to preferring the more intimate sound of him with Buddy Cole. 

I wonder if in the 50's did Sinatra and the rest finally catch up, or did Bing decide to back off a little due to the things going on in his personal life? - maybe someday Vol. 3 of his biography will clue us all in!

That's a good point. The 1950s are overlooked for some of the remaining boring arrangements by John Scott Trotter and the horrible backing of Buddy Cole. Bing's "concept" albums in the 1956-1959 period are great!
 

Richard Baker wrote:

Lobosco wrote:

That's a good point. The 1950s are overlooked for some of the remaining boring arrangements by John Scott Trotter and the horrible backing of Buddy Cole. Bing's "concept" albums in the 1956-1959 period are great!
 

I agree that latterly John Scott Trotter's arrangements had become somewhat "stale". They tended to be too rooted in the past. But Buddy Cole's "horrible backing"? As with all things, just as we have our own individual tastes, so performers meet those tastes to varying degrees, but Cole's small group or piano accompaniment was for me highly entertaining and Bing reacted very positively to the freewheeling possibilities. (Here I believe we must include all those radio tracks). The low points where Cole fails to meet my tastes were those in which he indulged himself with overlaying some of those recorded tracks with his wretched organ.   

Were the option available of awarding graded votes I think I would have placed my preferences in this order - 
1 1940s
2 1950s (the second part of the decade being the major influencing factor).
3 1970s
4 1930s
5 1920s 
Though I do very much like a selected few from the 20s.
The 1960s comes a poor last with those singalong LPs (though the first was recorded in late 1959, in practical reality I think it falls into 1960) getting minus points from me. However, we should not forget the album with Louis Armstrong or Holiday in Europe, (soon to be released on CD). 

I tend to be too harsh on Buddy Cole, and I agree with you. He is actually a good backer except when he uses that organ - one of my least favorite instruments!

If I could rank in order my favorite decades, it would be the following:

1. 1940s
2. 1950s
3. 1930s
4. 1970s
5. 1960s
6. 1920s
 

I Chose the 1940s because Bing's voice settled into a resonant baritone which meant he could sing country and jazz as well as standards from the great American songbook but i think overall the recording period from 1930 to 1950 showed Bing at his best, sadly from 1951 onwards at times Bing's choice of material from his commercial recordings as well as films started to include some truly dreadful songs like The Yodeling Ghost" and "Hoots Mon" which meant that other newer and younger singers were dominating the hit parade more.