The 700 Hoboes Project is a interesting collective project:
The site is inspired by the writings of author John Hodgman and his book Areas of My Expertise. It is meant as an homage to the wandering men and women who chose to ride the rails during and before The Great Depression, and not the contemporary urban (or rural) poor.
The initial idea of this project was invite 700 cartoonists volunteer to draw one hobo each. The project went very nice, and now it has 800 hoboes at the master list. That doesn’t mean the contributions are closed. They still open and if you want to contribute just need to send the images, following the rules of the site, via the Flickr group.