When approached for money, I feel the transaction is a little one sided in that basically homeless people just make the statement 'got any spare change' and you either fork it over or not. If I were approached and was given an interesting anecdote/saying/quote/fact/trivial tidbit, I would be happy to fork over a few coins.
Assuming the streetperson could read, welfare should supply flash cards containing one or two line statements, researched and processed by newly employed beggars whose job it was to read through journals/newspapers etc finding interesting things. Much like the news section/quote/joke of the day random generators on many homepages and searchengines, they would be like sidewalk pop up screens. The card would read - "CONFRONT PERSON AND SAY: Excuse me but, did you know that Glaciers store about 75% of the world's freshwater and if all land ice melted, sea level would rise approximately 70 meters {210 feet} worldwide. Could you spare a dollar?"
You would have to ensure the text was short, the example above might be a bit long, and that there were very few double ups as it would be painful to be getting the same info at each streetcorner. Each person would of course get a fresh supply of new cards at the end of each week, and the process would encourage the streetpeople to learn and source their own content - as the more interesting/humorous the statement the more likely they will get some money.-- benfrost, Mar 03 2001 Street performers who attempt to entertain, amuse or delight passersby in exchange for donations are certainly common enough; you're just suggesting a different flavor of busker.
I suspect those little factoids would become irritating, especially since they'd have to engage your attention directly for some period of time. At least the classic "Spare change?" protocol resolves quickly, one way or another, and more traditional buskers can do their thing without having to actually buttonhole passersby.
There are some buskers whose trade is delivering entertaining monologue rather than the more common musical performance, dancing, mime, magic tricks, etc.. This is close to what you describe, though I haven't heard any of them rattling off random factoids.-- egnor, Mar 03 2001 And eventually the homeless population would become smarter than the rest of the population, and they would band together in the streets, demanding homes and meals and an end to the world's glacier problem.-- dredcat7, Mar 03 2001 Quite often I run into homeless people who do have some sort of joke or one liner that attempts to soften you up. There is one guy who's turf is the crosswalk in front of the Art Institute of Chicago that has two jokes...one for crossing the road each way with the crowd. (He also sells StreetWise so that also qualifies for 'working' for his donation.)-- blahginger, Mar 03 2001 random, halfbakery