I'm not entirely sure which direction this thread wants to go in. I would just like to point out here that there is a huge difference between art that somebody doesn't personally like or prefer, and art that somebody doesn't personally "get." There's a whole world of thoughtful, well composed and executed artwork that is of no interest to me, but I still can respect it as a fan of visual art.
As an artist, illustrator, art teacher, and student working towards a master's degree in art education, this is actually something that I think about and discuss with people frequently, both in and out of the Magic community.

At first, I thought you meant, "pick out one of the worst cards in Magic history, and tell us why you like its art." In that case, I would have quickly run to my Wood Elemental stash and written up a dissertation on the matter.
Bill Copes, it seems as though you have no problem with the formal qualities of Indestructible Aura's artwork itself, but moreso some comical confusion over the conceptual qualities, which is fine, but a little different than what I initially thought this thread would entail. It definitely looks like the bird is rocking out pretty hard. It seems like a fitting illustration for an otherwise very strange card. The aesthetics of the illustration are also working brilliantly. (Great contrast, use of primary colors, overall composition of shapes.) I'd expect no less from Mark Poole.

So that leaves me confused as to where the "worst" quality comes in. I'm not looking to combat your thread. That's not my intention at all. I actually really like the idea. I'm just wondering what you meant with the use of the word "worst." What's the "worst" about this? The aesthetics? The concept? The card's playability? Maybe you meant "weird," "avant-garde," or "unique" card art and concepts?

I totally agree about Whippoorwill. The whole "not flying" thing has always been a favorite of mine. Mold Demon is hilariously bad as a creature, but I actually think the artwork is rather beautiful and unique.
To join in on the conversation, if we're talking about artwork that we love on an otherwise useless card, mine would have to be Alpha's "Ivory Cup." There's something, in general, about the extreme simplified, visual iconography of the old Vintage staples, such as the Moxen, Black Lotus, Ancestral Recall, Demonic Tutor, Mana Vault, Library of Alexandria, and so on. Something about Ivory Cup
visually fits into the same category of simplicity. It looks as though it would do something broken and belong in the same company as Candelabra of Tawnos or Sol Ring.

I'm a big fan of the shadows on the cup and the distinguished red shape made with the negative space of the background. The tilted composition for an otherwise symmetrical situation is a nice touch. I wish this card had an ability that made it fit into a Vintage deck somewhere. I mean, there's still the off chance that you could gain one life off somebody's Meddling Mage or Balance, right?

How long before we bring up the undisputed king of avant-garde Magic artwork? Nothing even comes close to the oddness of STASIS. Nothing screams "skip your untap step" quite like a mime and blindfolded coyote wearing boxing gloves balancing on a see-saw with a painter's palette floating in between them.
