With a new Monkey Island game on the way, let's see how advances in computer graphics and storage lead the characters to evolve. The early ones use great economy of design so that we can read a lot of ourselves and our own prejudices into each character. In sequels, the characters conform more to the artist's vision and less our own.
Guybrush
The Guybrush character has to be two things at once. He's a character in the story -- and a fairly stupid one. Also, he's you. As a character he should look stupid. But as a representation of the player, you have to project on to him. So you mustn't look down on him too much. The early versions use their lack of detail to make this work. In the later images he looks too stupid and it becomes harder to identify with him.
Elaine
In the early shots she looks like a fiesty and adventurous piratess. Is there anything more fanciable? First with hands on hips, then striding decisively into the future. Wow. In the later episodes she too becomes more realistic and annoying. By the end, she looks like a nag. (Errrrrr... not that all realistic women are annoying.) I recollect that her character went in that direction too. Let's hope she's more of an active character in the new adventures.
LeChuck
The second image is by far my favorite. The green pixelated skin does a great job of representing decomposing, rotten flesh. You can almost smell him. As the character develops he becomes less of an unpleasant adversary and arch enemy, and more of an elemental force of nature. His menace and malicious nature has translated into simple, raw power.
Where are they now?
The good news is that early pics and videos of Tales of Monkey island have a less dimwitted Guybrush, a fiestier Elaine, and a green, rotting Le Chuck. Just what I wanted.