I'm a multiple play through kind of guy myself. I don't really see a need to do everything in one playthrough. Don't try to put a round peg in a square hole.

If you answer your question here it's all well and good but that still leaves one question unanswered... WHO WAS PHONE?

Because you are Wesley Gibson (the movie version).

I just hope you can get into the DB sactuary without joining since there is a word wall in there.

Bloodlust.

Reason for joining the Dark Brotherhood?

What about something along the lines of the movie "Nikita"...

The fame/infamy system is more similar to the karma system that was introduced in Fallout 3; people will still know you for what you've done.

Just make two saves...I know it sounds ridiculous but if you'd like to make a character with a pure heart no crimes no evil thoughts (which im totally not again im actually very specific bout my char ) I suggest you do that

srry not much of help x_X

Believeing that the Empire's Justice System has failed and that the Dark Brotherhood are the true ones brining justice to the wicked. Evil onto evil, a swift death to evil from the black hand, and all that good stuff. Just think about it this way if somebody wants these people killed so bad they must have done something bad to deserve taht right?

Edit: Now that I think about it I'm so gonna role-play this for my second character!

Well my character Rashir Nashida is also chaotic nuetral. After being caught trying to kill a highest esteem noble, Rashir's story begins with him being led to execution. He escapes. Now on his own and the posessions he onced earned taken from him, Rashir goes to the better instincts of his, which is survival. He will join the Dark Brotherhood out of need and survival.

I hope the example gives you more idea on what direction you want to go with your character.

Your character is a drooling moron, sithis being the patron of drooling morons in every TES game.

Because their missions are most fun?

You were conditioned as a youth to obey your superiors, but it went horribly wrong and you always do what you are told. You accept every quest, reluctantly, doing as little harm as possible. When asked to steal, you only steal what you need to. When asked to kill, you only kill your target, and leave all others alive. Or something.

Revenge? Perhaps your family was killed by the DB, and the only way to find out who carried out the orders is to move up in the ranks to gain access to that information.

Or maybe one of the Speakers found you as an abandoned child and took you in and trained you and you owe them your loyalty, and perhaps even understand the need for removing certain individuals to keep the overall peace in Skyrim. The Empire vs. Rebel situation could have been prevented with a few key eliminations, thus saving many more lives from being killed in the ensuing war. Its not a glorious task, and you take no pleasure in it, but its a necessary task.

Your parents were members.

According to the basic tenets of psychoanolysis, the only driving force behind any human activity is the need to reproduce. It does not matter what the activity is: selecting clothes, buying a car, having social contacts, playing sports, getting an education, building a career, if there is no way to subconsciously connect it with better chances of having offspring, you will not be positively motivated to do it. That is simply the way biological beings are wired. Expending frustrated energy some other way, when no positive action seem to be available is a compensating alternative, but the source of mental energy and drive is still the same.

(By the way, playing videogames allows you to expend your frustrated energies while simultaneously fooling yourself into thinking that you are doing something positive to satisfy your inner needs, if you play a heroic figure.)

In this case, you wish to roleplay a character who has frustrated energies (unless being in the Dark Brotherhood somehow improves chances in courtship), and who compensates for them negatively by becoming an assassin. So the key thing is to come up with a reason why the character would be frustrated. Perhaps a bad love affair, professional setbacks, a financial dead end, thrown out of school, a nasty looking wart. There are many to pick from.

Why is everyone under the assumption that the character (role-playing wise) would think what they were doing is wrong? Perhaps they think what they are doing is right. Evil onto evil.

They threatened to kill your family? Blackmail? Donno.

Well my character in Oblivion was what I would call a mixed personality. He would take a "job" for the money, not because he got a thrill in killing, it was about the profit not the pleasure.... it was never personal.

I was recruited in the brotherhood after an incident with me and a town guard. We had a small dispute over an alleged "stolen" horse, unable to amicably settle our dispute the argument ended with the guard having an arrow sticking out of his eye socket. The next night I was visited by a mysterious individual who noticed my lack of hesitation in settling the dispute with a well placed arrow, and thought I would be a good addition to his organization.

Oddly enough as the brotherhood storyline played out I grew fond of my recruiter, he had a certain... panache. It became one of my favorite storylines in the game and was actually fairly sad when my.... mentor, met his unjustified fate.

This statement is hilariously self-contradicting.

Anyway, in this case I think right and wrong is probably in eye of the beholder. There may not be anything inherently wrong in playing an assassin, as long as one knows what it is all about, and fiction does not overlap with reality.

I didn't say it made logical sense, good and evil don't make any sense in general.

Just forget the whole "good-guy" type in the beginning and start out as an evil character in stead. Then you can start out by playing through the DB questline and when you have finished you experience some cruel act that completely changes your perspective on life. You decide that you want to redeem your sins by doing good, saving the world, slaying Alduin.
Everyone's a sinner and everyone has a dark passenger.

But I would rather play the chaotic neutral / neutral evil throughout the entire game as it makes for much more fun gaming IMO

power *shrug*

$$$

Chaotic World + Nature Balance + Gold + Fun