Because you really can't tell who's who, and unless you have unlimited means, you can't just give to everybody, I have a rule about who I give to - street entertainers.
They don't necessarily have to be any good, for example at the Tampa offramp from the 118 there used to be a guy with a clarinet... probably had no clue how to work the thing, but we found his godawful blatting so entertaining that as far as I was concerned, he had earned my dollar. This also goes for the occasional really awesome sign (but they'd better be really creative). One guy was near my current offramp in the last year or two with a sign that said "My Lear Jet ran out of fuel" and signed it "Hobo John". He got my dollar.
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