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?"