The Agent from Crackdown, he repeats useless phrases all the time then berates you for doing things that are unavoidable, like running over pedestrians!
Any of your allies from the Lego games.
Lets see if you can guess who this is:
"Hey! Listen! Hey! Listen! Hey! Listen! Hey! Listen!"
"WHAT? WHAT? WHAAAAT?!?
"I don't have anything to tell you right now but if I do, just press up C!"
"I'LL KILL YOU!!!"
Mission Vao, just for some reason I despise her.
Any of the characters from Enchanted Arms, if you have not played that game consider it a blessing!
Funnily enough, the Guildmaster is not annoying to me, mostly because you can turn him off.