Context is vital in busking. Frex, busking licenses for "Taste of Chicago" are expensive, but a good busker can make thousands of dollars there. Even some everyday street-corner buskers make impressive annual incomes.

Taking requests helps. Many buskers, if someone stops to listen, will pause at the end of a song and ask what they'd like to hear next. One at the Wentzville faire asked what language I'd like to hear next and started rattling off a list. I stopped him at Welsh -- and bought one of his albums on the spot.