This for a hobo? Tricky.
The essence though is pretty simple. Improvised and unexpected music. That and Jerry pulling faces. The good news: improvising music from a unexpected quarter is realtively easy. The bad news: that there are lots and lots of people doing it or have done it. Entire broadway shows are dedicated to it infact.
This is not insurmountable, but you have to find a unique (or as good as) hook to keep it fresh... The key is misdirection then surprise.
I noticed in your signature that you make cigarbox instruments. Could you possibly make one that is assemblable quickly? Could you disguise the parts as other things? The neck becomes a walking stick, the strings are, well, bits of string in your pocket, the cigar box is... a cigar box. I don't know... I am just making this up as I go along.
Oh I shouldn't forget the other part: the faces. When being a musical clown, enthusiasm and fun is 95% of the entertainment value, and musical skill 5%. At least that is my experience. I get my best reactions on guitar, when I strut around and dramatically play mock Flamenco music singing in a strong Spanish accent interspersed with mock Spanish (Sabo hablar espanol sorto kindo. Pero, me gusto mucho canto gobbledegooko de espanol, es mas hilario).
Just think about it some more and experiment. If you think something is just too stupid or absurd to work, try that first. You can always tone things down later.
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Snugglesnort the Rhymer.
"Humor is the only test of gravity, and gravity of humor; for a subject which will not bear raillery is suspicious, and a jest which will not bear serious examination is false wit." -- Aristotle
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