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A "Jimi Homeless" is a homeless musician who dresses like Jimi Hendrix and plays songs like "Purple Haze" or "Manic Depression" on the street for money. Can also apply to any homeless person who plays music on the street for money or to a musician who is not very good at playing music.
"He can't play guitar worth shit, he's just a Jimi Homeless."

"Hey look, is that the Jimi Homeless Experience?"
by Apeshit Quarterly Magazine October 26, 2011
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