There was a time when I wanted to create a traveling creative team called the "Vagrant Creatives". But in this case I'm referring to the homeless community, and their occasional extremely witty approach. To start I'll mention a Chicago legend. The lovingly named "Shakespeare Bum" who despite wearing tattered clothing and having a ratty beard, quotes flawlessly from Shakespeare towards people passing on the street. He calls every man "kind sir" and every women "fair maiden". Quite a schtick.
I'm also reminded of a story (I believe attributed to the former DDB rockstar Susan Gillette). Supposedly known for her humanity and kindness, she once saw a blind man with a sign that read "Blind. Please Give Money" or something of that nature. She asked the man if she could edit his sign, she did, and the man was stunned as person after person began giving him money. He asked her what the sign said, she replied "It's a beautiful day outside, and I can't see it." Powerful stuff this advertising.
And most recently I saw a beggar on the streets in San Francisco with a sign that read "I bet you a $1 you'll read this sign." I say any sign that makes me laugh out loud deserves at least a dollar. Hell, there are billboards worth thousands that don't even make me smirk.
Personally I'm a fan of stories, and I always reward good ones with my hard earned duckets.