Once, when I was a kid, I tried to buy something from the neighborhood ice cream truck using only play money. I had a wad of fake bills, totalling possibly thousands of fake dollars. Surely it would be worth at least a dime's worth of goodies. (Uh, no, said the ice cream man.)
Anyway, here's another even more amusing story about someone trying to use his humble artwork to help pay the bills.
Broke Man Tries Paying Bill With a Picture of a Spider