An agent dresses like a typical tourist and walks down Hollywood Boulevard or some other heavily-trafficked area. When a panhandler inevitably asks for "spare change", the agent says, rather sympathetically, "What's your name?" If the bum tells him, someone quickly fashions a "Price is Right"-style nametag with magic marker and posterboard, and the agent says "Well, Joe (or whoever), I'll give you a dollar...IF...you can tell me the capital of Vermont. Because you're on the game show where you can go from beggar to bigshot...THE BUM'S RUSH!"
A handful of "crew" shows up with cameras and mics, and maybe even a podium for the host and/or a stand for the contestant. The host then asks a series of trivia questions, and the bum can risk his winnings each time to go on for bigger money and/or prizes, up to, say, $50 or $100 (chipped in by the group), or gift certificates for food, clothes, a hotel stay, etc. Any other agents could be enthusiastic audience members who shout out answers to the contestant if he chooses his "ask the audience" option (assuming he doesn't know the capital of Vermont, or who played Gilligan, or who was the 16th president).
The bottom line would be that the bum would actually receive the goods no matter what (just make sure Charles Van Doren isn't one of the contestants), so that act of charity might undo the humiliation we're actually putting him through. I dunno. It could also be called "Street Smarts" (although that was taken by Leno), or maybe "Brother, Can you Spare a Dime?" (where dollar amounts would go up in multiples of ten (a dime, a dollar, ten dollars, a hundred dollars).
Thoughts?
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