I'll give money to people on the street if they are doing something. Plastic bucket drummers, mimes, dancers, sax players, singers -- do SOMETHING and I'll do something in return. Be part of the city, not just a leech!
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We don't have too many of those. Used to have one fella -- guess he was maybe middle aged at the time -- played a sax for whatever you could spare. He was good too. Don't know why he couldn't make it as a professional musician, or maybe he did, and lost it all. I used to make requests...or sometimes he'd see me coming and start playing something he remembered I liked. Haven't seen him for a long time...wonder what happened to him.
I once gave $20 to a Jamaican guy in New York City who played kettle drums in Times Square. At first I thought he was just plain "good," but I was amazed to see that he could play any tune that any random passerby requested. It's one thing to hear someone like that play "Yankee Doodle Dandee" or "Mary Had a Little Lamb" -- those folks are a dime a dozen -- but there must have been several hundred people gathered around him when people realized that this guy could play requests that included the theme song from "Raiders of the Lost Ark," Rossini's "William Tell Overture," "In-A-Gadda-Da-Vida" by Iron Butterfly, and a number of scores from Bach's "Brandenburg Concerto."