The limitations to the poll system on this forum (i.e. not allowing 200+ entries) mean that it's ill suited for this. For my "other", I'm tempted to put Minsc from Baldur's Gate. Between the unpredictability of his berserker ability, his random comments during battle, his "giant space hamster" and obsession with "the forces of good", he's the only character who has ever convinced me I was administrating a Special Olympics training camp.
"Boo likes the forest!"
"Evil, meet sword! Sword, meet evil!"
"Buttkicking for goodness!"
"You should be carefull with those you trust. Not all are as loyal as Minsc and Boo."
On the other end of the spectrum is the character that convinced me I was operating a Jedi work program for the criminally insane, HK 47. "Love is making a shot to the knees of a target at 1000 yards with an Aratech sniper rifle and a Tri-light scope."