Jeremyrose,

I am afraid that my choice isn't particularly original, but I would say his 1930s version of "Sweet Georgia Brown," which to me is the quintessential Bing jazz recording. I love the backing band and, of course, Bing's scatting and his very fast final line, "They call her Miss Sweet Georgia Brown!"

And then, perhaps I would add the 1957 album Bing with a Beat, with Bob Scobey's Frisco Jazz Band.

Jeremy,
You make it too hard.
'Dinah', 'Some of these days', 'Shine', Sweet Georgia and so on.
Yes, I like 'That's a Plenty' as well. Would 'Rhythm on the River' count??
Too hard - think I'll have a coffee.

jeremyrose wrote:

Artie Shaw famously said, "The thing you have to understand about Bing Crosby is that he was the first hip white person born in the United States.".

Hmm  -- -  and Hmmm  again.

Within the confines of that question - "THE FIRST" just has to focus on the earliest period. Or is the birth date combined with a much later performance adequate evidence to prove the proposition? Possibly not, because surely that does not prove  that any new path is being trodden, and I think Artie was making a point about Bing starting something new.

And yes, Jeremy, I realise you set the question and came up with an answer from a much later period,  but I think that any answer that focuses on anything later than early thirties is open to challenge.. 

My answers therefore concentrate on the very early solos with Whiteman or just after, and my initial shortlist has to include "Mary" from 1927, and "Old Man River"  from early 1928 both of which display rhythmic and phrasing originality in the context of a white singer. Then there is just possibly "From Monday On" and "Tain't So Honey, 'tain't So" from mid 1928.  Advancing a little in time, there is "Dinah"  from 1931 with the Mills Brothers and from 1932 there is "St Louis Blues" with the Duke.

From this short list I personally would select "Mary", partly because it is the first, and partly because I like it. Surely anything much later is, in my view, open to the challenge of "proposition unproven", because by then some followers and imitaters were beginning to take the same path - less successfully certainly, for some years, but if you take performances from the 40s and 50s you have examples from other performers that could be "used in evidence"!
 

Jeremy,
I'm in Washington State - 9 hours behind you.
As Anita says, she comes from Washington AC (above California) and not DC.
I think I like BC - below Canada.
'Ol' Man River' - Bing's earlier version was really moving it along, just like in the later years.
In the 40's he made 2 recordings of the song but in different tempos compared to other recordings of it.
I like the upbeat of the early and latter versions, but I like Paul Robeson's version, which is much slower.
Peter Dawson would have recorded it and he is the only other singer to have pumped out so many records - may have done more than Bing, but Bing probably sang more than Peter because of the advent of the wireless and TV.
I believe it's hot BIA. Cool here.

Like, Richard, I think if you want to verify Bing's FIRST-ness in this category, then I think you do need to select something from the late 1920's or early 1930's, like "'Taint So" or another number in which Bing's even scat sings.  I keep thinking of "Young and Healthy"; I can't recall if it actually contains scatting, but the rhythmic singing is certainly innovative for its time.

If the idea is to show that Bing was indeed HIP at sometime in his career, then my selection (drawn from radio not just records) might be "Choo-Choo-Boogie," "Route 66" (with Andrews Sisters, I think it is), "Now You Has Jazz," or even a ballad like "I Can't Get Started," with Rosie. Suddenly, too many others are coming to mind.

Keep in mind, however, that Shaw probably isn't just talking about Bing's songs.  He's talking about Bing's way of listenting to, laughing along with, and going about working with members of the band.  He's talking about what Bing paid attention to in music, songs, life--about what kind of importance Bing gave those things.  This is something the authors of The Hollow Man book didn't understand, when they try to run down Bing with an example of when he ditched one or two nights with Arnheim's band (I think it was) in order to drive over a hundred miles to hear Armstrong play.  To their feeble minds, this showed how irresponsible and undeserving Bing was.  Shaw would have understood that the Bing he was talking about HAD TO do that,because of the value he placed on Armstrong's music, knowing that music was good for his soul and his growing in his chosen art.