The priest ranting in Whiterun
The kiss ass elf at the College
Delphine
The two assclown brothers in Falkreath
I hate Maven Black-Briar... or maybe I love her. Not sure.
That guy stuck in the web whining while I loot spider eggs.
Kiss ass elf? You mean Nirya or Faralda?
I don't like her general attitude with looking down at everyone no matter how helpful you are, you are directly responsible for getting her into the throne as Jarl and she still talks down to you like you're inferior. She clearly finds out later about you being dragonborn since, well, how else would she know how she got the throne? I like the fact that she's so well connected, but I don't like how they don't give you the opportunity to tell her you're 2nd in command of the Dark Brotherhood when she threatens you with them. Even a single line of dialogue is all that's needed: "Bitch, I RUN the Dark Brotherhood and I saved them!" She would have a ready quip either way but still. Plus, any scenario where one or another faction is brought up or perhaps those who act all high and mighty toward you after all you go through (slaying giants, both kinds of trolls, mammoths, dragons, vampires, cultists, various creatures, giant centurion animatons, armies of twisted Falmer which NOBODY likes to tangle with, etc). This goes straight to a good chunk of the Thieves Guild. This is also a reason why I like Delvin so much, even when he doesn't know you, he's at least respectable. He doesn't talk down to you, he doesn't trash talk you unless you fluff up, and he at least shows gratification when you succeed.
This also kind of takes from what they say "he who speaks doesn't know and he who knows doesn't speak".
They don't HAVE to say anything if it's true, they don't have to say anything if they don't want to so most who don't normally speak about their past or anything of the sort, they usually know what they're doing and why it's also widely commonly said "Don't trust the quiet ones". Whether it's because they're twisted and insane, secretly evil and plotting, or perhaps they're that assassin/fighter who you do NOT want to mess with. This doesn't mean ALL who are quiet are those who you should fear.
PROTIP: If you know a lot of something that normally could be considered something to be respected and feared like you are a well experienced fighter, drop a few indirect hints so that they conjure up all sorts of fun gossip but don't brag about it. Such as teach someone how to do something trivial but not what the common folks would know, don't say you're a master but still teach folks fun and trivial things so it gets them thinking. If need be, you can say "oh, I trained such and such" or "you should check out this place when you're in the area because when I used to train there, it was..." but NEVER go into full detail about your escapades until you're a retired old goat. That way you have plenty to share before you're gone.
I wish we had more things to share with the thieves guild MISC. members, half of them are pretty decent people and at least Sapphire has a background story as to why she's the way she is. I just wish she was nicer to the female characters who speak with her since it were men... ohhhhhh... nevermind.