" I love superbad, what a great site!
Except, I don't understand."
Seems like you understand it perfectly, you love it, and think it's a great site. That's all it is, that's all that site has ever been, it's been around a long time, he changes it around now and then, adds stuff. There's nothing to understand, that's why I mentioned that site as one of the very few I've ever seen that I consider to be art.
" Does something have to be meningless outside its own context to be considered art?"
Art isn't meaningless outside of its own context, that's what makes it so valuable, and why it's given so much respect. It communicates to people, it's a sort of meta language. It carries a far greater meaning than craft, that's why people pay a lot of money for art.
You can make the term art as loose as you want, the looser you make it, the less useful it is. However, in this context, from the first posting, it's sounds to me that you are referring to art in the stricter sense of fine art, the stuff you learn about in art school, literature classes etc. If you're talking about art as a product of human activities, then anything done well is art, but that makes it so broad that the term doesn't have much utility. Van Gogh made art, a commercial illustrator or web designer makes, well, commercial illustration/web design. It can be very well done, but it was done for a reason outside of itself, it has some purpose or function outside of the creative process.
This doesn't mean art is 'meaningless outside of its own context', it just means that art occupies a higher position on the scale of creative endeavors than well done craft like web stuff. Very few artists have any difficulty seeing this distinction by the way, although I think they might tend to respect high quality craft more than most people, since it requires many of the same skills and discipline to create.
"Does a craft honed to perfection not qualify?"
A craft honed to perfection is a craft honed to perfection, as you said. I think there's a certain tendency to denigrate craft, artisanship, and because of that, a corresponding tendency to want to call craft art, to bring it back up to the level it should be. In the looser sense craft is absolutely art, without any question, look up art in a good dictionary and that's the definition, but that's not what you were asking, at least not the way I read your question.
My websites are finely crafted, and some of my programming stuff has been accused of being 'art', but as far as I'm concerned, it's just well done engineering, which may or may not be used to contain or do something of greater value. The same exact site code and programming and design could contain different things, it's just a container, like the frame of a painting. I try not to confuse the quality of the frame with the quality of the painting.
Anyway, I started web stuff thinking it could be art, but after doing it for long enough I don't think that anymore. That doesn't stop me from applying very high levels of craftsmanship to my stuff, but I don't think it's art at all, it's just well crafted.
<sorry tedster... >