As an interesting side note, I saw that, if you reverse the order of the Top 100 List so that it shows you the Bottom 100, five of the six games from that article are listed. The one that's not? Risk. Which is interesting, given what I'm about to say.
Anyway. Here's what the Cracked article has to say about Risk:
The worst part of Risk is victory by excruciation. A well-designed game has tactics and skill building to a climax, a thrilling race to victory, and when someone has clearly won, it's because the game is over. In Risk, someone can win hours before it ends, and they will not let you just admit it and leave. They spent hours carefully planning this victory, and by God you are going to sit there and patiently lose for just as many hours so that they can enjoy it properly. They've turned having fun into a zero-sum game.