I generally don't give money directly to the homeless\people on the road asking for money, although I do occasionally give directly to homeless shelters. However, I will make the rare exception for a really good sign. I saw my all-time favorite the other day: "Ninjas killed my family. Need money for Kung Fu lessons"
I despise hobos, but... here it goes, the CLASSIC ONE for all IT peeps or just Web Designer peeps: In fact, I use this one at work.
The corner of Aurora and Denny in Seattle. I feel kinda bummed that it's been used other places (judging by Lil Pun's pictures). I thought it was original, but maybe the dude just plagiarized it.
Not really a sign, but in San Francisco, I had a beggar come up to me and ask for a donation the the "United Negro Cheeseburger Fund". I give as I can anyway, but I gave a little more joyfully to him.
Ah...good old Wilson. He once worked as a pool cleaner for my friend's company. He's a true pro on the north side. He carries about 10 different signs. I've left early enough for work on days to see him leaving his neighborhood there off of Parmer behind the Kwik Lube.
the guy who hangs out at the corner of 610 and westheimer with the sign "visions of a cheeseburger" is the best