22. The Originator

It's become a cliche, the "Why Lie? I Need a Beer" sign (Jada has bars about it—that's how you know it's trite), but this man scores points for asking for everything; he wants the world. That, combined with the grainy texture of the photo and his clothes suggest that he's also a pioneer. He probably had this sign way before all the other bums. Salute.