Doom Guy ~ 30 min, Painter IX.5
Here's the thing. For such a simple dude, a little clay dude that is at most either a tiny sprite guy based off a little clay guy or a a guy filling up only part of a 320x200 screen, the Doom Guy is awful hard to draw right.
I think it has something to do with the really unusual center of balance, especially in the shooting sprite from which this was drawn. He's practically falling over. That and his unusually stout proportions. Doom guy: he's an original.