This is why hipsters are pessimists.

I think there is definitely something suspect about the "way cool/sold out" dialectic, as I am haunted by it constantly, and perpetually trying to overcome it.
When something becomes popular, it in no way loses meaning or value, except perhaps to the people who believe rare/underground art loses value once popular. I suppose it loses value to them, as it is no longer valuable to suggest said art to a peer-and that person becomes less of an authority with withheld knowledge, and more of a subject to something more all-encompassing. But losing meaning? That just seems unfair to the artist. Even if the meaning to someone is "that annoying song that used to be cool till it got a commercial", it still has significant meaning. Regardless, I personally feel that art does not lose meaning or value when popularized.
I think that perhaps this perception of art losing meaning could be attributed to our oversaturated art-world. We, as a generation, are quickly disenchanted with works that become popularized-we always need the unheard or the untapped, something new, something better. Perhaps the label "the wikipedia generation" can explain this. Even though we probably smoke more pot and play more video games than any generation to precede us, each and every one of us has a plethora of trivial and non-trivial knowledge jammed up in our brains. From frat boys to hipsters and back again. I foresee game shows becoming more difficult in the next decade...Anyway, we have always known what it's like to be an authority on a selection of subjects. We're the first computer savvy generation, and that has always been something to dangle over the heads of everyone else. When a piece of knowledge breaks the confines of our minds, or our social groups, and becomes popular or well known, it is no longer of use. It is no longer as valuable to us. Do I think this is a good thing? Absolutely not. We need to overcome this, as the media can easily find and use our little underground secrets against us at their leisure. Plus, we're missing out on great art, when we write it off as commercial or corporate (unless it's a corporate response work, then protest all you want).
And I like "Wraith Pinned to the Mist", dammit, I don't care if it's in an outback commercial.