This is one of my favourite web stories. A few years back, John Hodgman published a book titled The Areas of My Expertise, a collection of random things, one of which was a list of the 700 all-time greatest hobo names. Soon after, people started posting illustrations of their interpretations of these names on Flickr and tagging them with "700hoboes".
At this point, all 700 have been illustrated at least once, with over a hundred people submitting a picture. The whole thing even has it's own site at e-hobo.com. Here's an interview with Adam Koford who initially set up the Flickr group.