So there are some things I wanna do in OB that dont fit my current character, mostly things of the evil persuasion. Cheza isn't purely good but she's not bad, just naive and confused, so things like the DB don't fit. So I need a new character but I'm having a really hard time coming up with a back story that justifies such terrible things as assassinations that isn't just full of cliche. All I've been able to nail down for sure is its gonna be a male, probably a Breton and a mage.

So I'm looking for some help either in the form of suggestions or examples of successful evil RPs (I won't steal them just use for inspiration). So please my creativity is a shallow pool and we're in the dry season lol

Why don't you just follow them around what they do and try to work it out when you're playing? Pay attention to how they act when they do these things, see if they'll drop any hints. I did this with a character once. When I found out why they ended up in prison in the first place, it was incredibly satisfying.

+1 this.
As I said before, it's easier if you don't try to drive, just let the story play out organically
I'll give you an example - Vilja inhabits Niamh's world, and when Niamh first met her she was a relatively naive would-be alchemist on a search for herbs for her sister - (long story!) - and not much else. After a while of adventuring however she has multiple scars, a tattoo all down one arm, she's very handy with a 2 handed blade and she's probably killed as many people as Niamh has.
I never knew how the story would go, and I still don't - but it seems to work nevertheless.
Here's a link to Niamh's backstory and a couple of vignettes I've written - just for reference: http://www.gamesas.com/topic/1309222-niamh/page__view__findpost__p__19691372

I find it's better to stay away from stereotypes. A Breton mage wouldn't inspire me to roleplay anything. But an Orc mage! Now that would make me wonder. How did an Orc ever happen to become a Mage? What led to this decision? What kind of Orc would make such a decision? Before I know it I'm putting together a vivid character in my mind.

One of my favorite character templates has been Breton warrior. I've roleplayed one of these in each of the last three games and each time the character has gone in some direction I never expected. In Oblivion my Breton warrior was a character who had forsworn (no pun intended) (unless it's funny, in which case I intended it) her magical heritage, for reasons that had to do with her father. She decided she would not spend her life studying books in libraries, she would be different. This character started out like my other Breton warriors, but something odd happened partway through the game that I didn't expect. She began to use magic. She found herself in a jam and surprised both of us by instinctively flinging a Flare. And, little by little, she began, cautiously, judiciously, to bring magic back into her life. By the end of her story she had embraced her heritage and left Cyrodiil to attempt a reconciliation with her father.

In Skyrim right now I am planning to play an Altmer thief. I don't know why an Altmer thief caught my fancy and I don't really need to know. I just need to know that the idea clicks. I am in the process of answering the usual questions: why did an Altmer ever decide to become a thief? There must be some story there. What is it? Exactly how did this happen? When I have answered those questions I will know that it's time to play.

My current mage:

I kinda wanted him to be evil. But instead, he showed me that he was a good guy. So I'm going with what he wants. Perhaps another play then.
Another character from last year (in its most basic form):
Prison for murder.
Pissed and anti-social. Learned that he would have to better his social graces if he wanted to join the University. Did so, and grew to enjoy the friendship of many. Journeyed to the SI. Went insane there, returning to thoughts about harbored resentment. Returned to Cyrodiil, infected by vampire, retired to Anvil house for certain... perks of the house. Enjoyed being evil for a long time. Started quest to help unify necromancers. (self-imposed.) After a while, came to regret many decisions. KOTN for repentance.

I’m another follow-the-character player, so I thought I was going to have to make a throwaway character just to mechanically go through the Thieves Guild and Dark Brotherhood questlines so that I could see what they were about, but not really try to role play.

Then my first character had a left for dead experience that sent her on a downward spiral. She joined the Thieves Guild just to try to feel something again, but in the long run it was a letdown. During her Arena days she picked up a DB invitation. Since the old rules didn’t apply any more, she gave it a try.

Wham, thrills again. Eventually her conscience returned. She dumped all of her junk in a house and headed out on a pilgrimage wearing sackcloth. Redemption. If I had tried to plan all of that, I’m sure it would have been flat.

Probably full of cliché, but also a very satisfying game that just happened as we played. Hope it helps.

@Pseron Wyrd my choice of Breton is a practical decision more so then an RP one, I svck at being a mage and need all the help I can get, tho your point is a good one.

I appreciative the replys very much you guys have given me much to consider. Surprisingly I've been getting more ideas about Cheza's future then my new characters tho. There is a story here brewing, I just need to draw it out!

DarkHumbug and PhonAntiPhon, you two have answered a question I didn't know I've asked. Forget a new character thanks to you two I've got a half page written for Cheza, tying in events I thought were meaningless and leading the story somewhere interesting. Thank you!

You're welcome

It'll happen. It always does if your brain is in a creative space.

That sounds to me like a cliche-within-a-cliche. Why wouldn't orcs be mages? Why would Altmeri not be thieves? The cultural stereotype is still there, it's just inverted.

The OP asked for suggestions to stimulate his roleplaying. I suggested that it might be useful to think outside the box. When we run out of ideas or are not inspired by the ideas we do have, one strategy is to turn conventional ideas on their heads. Breton mage not doing it for you? Try an Orc mage. That Nord warrior build leaving you cold? Try an Altmer warrior. See if that inspires you. Juxtapose two ideas you don't normally think of putting together. Thay might generate some heat and light in your imagination. Even if you can't use that idea it might lead you, eventually, to another idea, one you can use.

If you're uninspired, I have found, the one thing you don't want to do is continue thinking the same thoughts. You're not going to get anywhere doing that. Performing various mental excercises such as the one I suggested is one way of breaking out of old habits of thought.