Cryptic Billboard on the 33: Lost Bet?

I’ve driven past this billboard several times, and finally managed to snap a quick picture of it. I posted it to Facebook and Twitter, asking, WTF?!  It reeks of a political hit mailer, and it’s clearly not selling anything. 

I received a bunch of speculation, but one answer seems plausible, and was repeated a few times by different people. The guys in the picture lost a bet, and this is what the winners selected as their “punishment”. If anyone knows the story, or knows who they are, or what the bet was over, I’d love to know. 

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