Brother, Can You Spare A Dime?

Once I built a railroad, I made it run
Made it race against time
Once I built a railroad, now it's done
Brother, can you spare a dime? 

I admire Bing Crosby's vocals but they've always struck me as more emotionally remote compared to Sinatra.  And I can't imagine Bing singing a torch song like Frank.

Brother, Can You Spare A Dime? is an exception.  With lyrics by Yip Harburg, music by Jay Gorney, and recorded in 1932 at the height of the Depression, Bing perfectly captures the pathos of the time, and the personal tragedies. As we progress through verse and chorus the narrator becomes more desperate, transitioning from speaking of his "brother" to the more impersonal "buddy", as friendship shatters in the ruins:

Say, don't you remember, they called me Al
It was Al all the time
Why don't you remember, I'm your pal
Say buddy, can you spare a dime?

Harburg, best known as composer of Somewhere Over the Rainbow, and Gorney were songwriting partners for several years until Yip ran off with Gorney's wife.