Sad thing is they do them in chalk so they wash away - they need to PAINT them on the sidewalk with permanent PAINT!
most of this kind of art is done on public/government owned property, he just stops somewhere that he thinks he could make some great artwork and goes to work. Sometimes his (and other sidewalk artists) get run off their sites even when they've put days into it and aren't finished yet. I'm sure they could/would get into serious trouble if it were permanent. But I'm sure they make money to draw things for people who'll pay.
I believe this guy even did a drawing for President Clinton for his inauguration. Someone (us tax payers) paid for that.