This Build is by far the most fun to play i have ever constructed. I play this one for my Khajiit and it has made him my favorite character just because of how he handles combat. This is The Trickster

Race: Any (Khajiit and Argonian work best)
Skill Trees: Sneak, Illusion, Alchemy, Pickpocket Light Armor (optional)
RP Items: Jester Clothes
Stone: Shadow, Serpent
Shout: Throw Voice
Discussion: The Trickster is a class that does not kill ANYONE directly but instead "causes" the death of his foes. This class requires perfect stealth, perfect Illusion, and perfect Alchemy so train these as quickly as possible. Stock up on Poisons (Damage Health and Frenzy), learn the basic illusion spells (Fury, Fear, Muffle), and get really good at Pickpocketing. Now whenever you enter (example) a fort and there are more than 1 enemy stealthily use Fury to make them fight each other over and over again until there is only 1 Now quietly sneak up on him and place some poison in his pocket. If you have no poisons strong enough then just sneak away or use fear to make him run so you can collect the dead's loot. The point is to never use or even have a weapon so you never directly kill anyone. My Khajiit uses his fists IF i get forced into combat but otherwise i try to stay out of combat.

Challenge: I challenge anyone to try this and make it to level 30 (any difficulty) without leveling up any weapon skills. The Thieve's guild radiant quests are the best way to do this, as well as DB radiants if you make the townsfolk kill your target for you.

Good Way to improve Pickpocket: In Windhelm there is a beggar who trains you in PP, get the training and then PP all your money back. At higher levels where you give more money it will be really impossible to make this work so do only 1 training session at a time. Be sure to save often.

Good Way to train illusion: Use Courage on random people over and over again. It is not a hostile spell so no bounty.

Thoughts and Comments?