John Hodgeman, Daily Show funny man aka PC, wrote a book called Areas of My Expertise. A chapter of this book is a listing of 700 hobo names (he added another 100 for the paperback release.) Hodgeman read all of the names for the audio book release in one take with Jonathon Coulton in the recording studio accompanying him on the guitar.
Now, the hobo list hits the web with E-Hobo.com. This link will take you to the full 800 name with the illustrations web-nerds have created for each of them http://e-hobo.com/hoboes/list/
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From the names it looks like some of the hobo's are ex-mafia members.
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