Mystery Ad Man

OK, who is this homeless drifter, and why is he suddenly popping up on every website I see?

Obviously he's a piece of clip art, given that he's featured in three different ads as three different people. I'm curious as to who thought a photo of an unkempt sleepy-eyed Dead fan would make a good spokesperson for their business. When you pick a person to be your mascot, they become the face of your company. Who thought this was a good face?

And what's up with that first ad? He's definitely not a mom. Did anyone even proofread these ads?