I would totally buy the Roy Lichenstein label, he's my favorite contemporary artist. I have a print of his in my room, actually.

There was a vineyard I visited in Santa Barbara where each label was hand painted (it was a very low volume place, haha), and I guess the hand painted quality spoke to its exclusivity and meant it had to be good (that, and the $70 price).

I think when you're looking at ones priced under $20 bucks, the artwork on the label probably shouldn't mean anything one way or the other. They could be hiding the fact there wine isn't that good with cute animals or marketing messages at their targeted audience. Or, they could just be perfectionists and want the bottle to look as nice as the wine its holding.

Likewise, I'm equally skeptical as the writing on the back. If they have four to five sentences about the vineyard and use all sorts of fluff language but never once explain how the wine will taste, smell, or how it is made, I'm skeptical.

Your best bet is still to judge based on where it was grown (both country and region), the style of wine & varietals in it, and from there, if the sommilier or salesperson has an experience or can make a recommendation. I usually pick what I'm interested in and a price, then ask someone to help (i.e. I want a white bordeaux, or something that tastes similiar, for under $20.)

As far as those bordeaux and chateneuf du pape pictured above, those regions are known for their wine, there is no reason to invest that much time and energy on the label. In fact, in Bordeaux especially, there is a very conservative culture based on the grapes and terrior, so it seems fishy. The C-D-P, however, has more of a standard label, they just took a little more energy to make the label a little nicer than your average one - I'm guessing that is an expensive wine. The bordeaux, I'm guessing, is cheap, and not grown in a very old or presitigious part of bordeaux - just a guess though.

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