Wow, that's some impressive threadomancy.
But, to answer the OP (very late) - I'd also go with a lot of the Jeff Dee stuff. And Erol Otis. And, to be honest, a lot of the Elmore stuff as well. When he didn't do cheesecake, he did some fantastic stuff. I was a bit of a Dragonlance geek way back when too.
There was also a really cool image way back in the old loose leaf 2e Monster Manuals. It was on one of dividers that came with the set. It showed a group trying to get past a beholder type guardian critter (spectator maybe) by feeding it a big hunk of steak. Very cool image. Can't find it though on Google and I have no idea who did it.
Two things I always miss about that early stuff. One, PC's getting their asses kicked. The monster manual entries and even the DMG and PHB often showed the monsters munching on a PC. That's missing from a lot of the current art. I also miss the whimsy. A lot of that older stuff was pretty silly. There's nothing wrong with silly. We need more silly in the game.