If you are homeless it pays to be creative with your sign making. If I were to pass a homeless guy on the street with a funny sign, I would be 10x more likely to cough up some cash to drop in the collection bucket. Shown below are some of the best homeless signs ever created.
This guys fake smile is not helping his cause, but his sign is pretty funny
Homeless Bill has the right idea. Something tells me he has a decent shot of getting what he is asking for. 
This pair of homeless people seen to be doing good. They are collecting some hard earned cash in this image. Not sure how they prevent going to jail though
Obama fans might give him money
This woman is likely making a killing with this sign. 
This guy has taken an interesting approach
Now this is how you make a living at begging for money. He likely spent quite a bit on this suit, but you know what they say: “It takes money to make money”.
His sign reads: Help me – I am a disabled clone war vet – Need $$$ to build death star.
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