What is the origin of a poor man in a barrel with straps that you often see in cartoons? Is it just an old vaudeville allusion?
I belive that Diogenes the Cynic (the philosopher, not the poster) was said to have lived in a barrel as part of his efforts to eschew material possesions back in the 4th century B.C… My guess is that that is the origin of the meme.
http://www.athensguide.com/journalists/articles/honestman.htm
I too have to figure Diogenes was the source.
I always thought that the cliche was of someone who had just literally “lost his shirt” gambling, and had to cover himself with whatever was available.
The idea of wearing (as opposed to living in) a barrel goes back at least as far as the US Civil War. I have seen a Civil War era photograph of soldiers being punished by being forced to wear barrels (in the manner described in the OP) while drilling. The caption of the photo said that this was a time-honored method for disciplining soldiers, so it was apparently already an old and traditional practice by 1861.
How (or whether) this ties in to the association with poverty, I don’t know.