Probably the most despicable is to burn the Guild of Heroes to the ground just for kicks. He starts as a smug, being pretty obviously evil when he gives to the people of the Arena a fight to the death (a very obvious good/evil choice for the Hero), then he goes with the "you know, I'm gonna reunite you with Mama! Wasn't she hot and everything?" Then he goes and lets you find your mother, captures you, makes your living life a nightmare, you escape, he finds the secret of your heritage and something, drives the world into darkness, forces you and other Heroes to fight his Minions, etc. etc.
So...seems like a pretty strong villain, considering that he achieves (to a point) what he wanted; near-absolute power by holding the most powerful weapon in existence, the Sword of Kings. So why he's just one inch below greatness?
You see...the first Fable isn't very strong on narrative. It tries to be non-linear and open, and the story is more about how your Hero goes to be the paragon of virtue, a common murderer and ne'er-do-well, or outright worse than Jack himself. So, you could have expected to have something like...I dunno, fighting yourself as the opposite of what you are (your evil urges if Good, your conscience if Evil, and your indecisiveness if "Neutral"), so having someone so desperately try to be hated with such an empty reason makes him fall very short of the right spot. Looking at his actions, you may expect him to act quite right on what he does, and he certainly acts the despicable part. But, had there been more meat to that story, that would have been magnificent; Jack could have certainly been the most despicable of all villains, just because he treats you like nothing. But he appears pretty much halfway through the story, and suddenly everything seems to be hammered into him: the sack of Oakvale, your training (through Maze), the sorrows of the main character's sister (through slavery and blindness), and more. It's all so sudden, and you get lost on the idea of "hey, I can be a tycoon at the cities!" or "hey, should I be a mighty Paladin or a brutal Assassin or what?" that it kinda misses the point.
Perhaps if the game had been much longer, the narrative a bit better explained, giving some earlier hints about his existence, and then the sudden twist of revealing that Jack is just a reflection of the Evil you could have been (or the Evil you could be) would have been masterful. Perhaps it's the smugness that rubs off the wrong way, perhaps it's because Molyneux sucks at doing narrative, but he falls real short of the target.
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