There are so many iconic and fantastic characters from Tolkien's created universe... and the best of them are hard to pit against each other because it's like apples to oranges. That said, I'm doing it anyway. I'm putting down all the characters I think are the coolest... that means this list isn't going to be EVERY character from Middle-Earth, only the cool ones. I'm going to open it up for you guys to add to, in case someone wants to add Tom Bombadil or Radagast.
list ordered by
Zachthemusicmage added Morgoth
Witch-king of Angmar
MatthewNeilan added Tom Bombadil
Darklord Ayush added Radagast the Brown
MatthewNeilan added Beorn
MatthewNeilan added Kili