The best sort of meme is one which you can use for multiple different purposes. In the case of 'too damn high,' we've used it seen in all kinds of contexts. Music fans use it when their favorite bands announce the prices for their new concert dates. Young people use it when they're trying to find somewhere to live, and they're bemoaning the price of rent. We've also seen party animals use it when they've slightly overdone it the night before.
The picture is actually of a man named Jimmy McMillan, and was taken during 2010 when he was trying to get elected as the governor of New York. He wasn't successful that time around, but he tried again four years later, and this time he managed it. We guess the barrier for entry wasn't 'too damn high' that time around.