It seems to me that you would have had to have already beaten the game at least once and already know the entire plot and when to trigger specific events if you want to actually play someone like a Thief, or an Assassin, or one that's both of them and really enjoys killing for the sake of killing and doesn't really care too much about anyone or anything. The reason it would be impossible to play is because the main quest forces the "Hero" mantle upon your shoulders, whether you want it or not.

The only reason I would bother with killing dragons is because:

1. It's bad for my own personal gain if there's no one left for me to kill or pillage.
2. It's bad for my own personal gain if I'm dead.
3. The game does not allow me to make deals with dragons;
Otherwise, I would just let the dragons fly around killing whoever they wanted, because I simply don't care about any of these people. If I want to play this kind of character, it seems as though I have to skip the main quest entirely and do everything else before triggering the dragon events. The Brotherhood for example, likes to be "known" yet remain entirely in the shadows and not have any specific member actually known to the general public. If I wanted to be part of the Brotherhood, yet was going around "saving the day" from all of these dragon attacks, you would think I'd be pretty damn popular. Even if I didn't go around announcing that I was a member of the Brotherhood, eventually the people I was contracted to work with would realize who I was and the word would spread.

I'm not really complaining per se (I'm really not), but does anyone else find this an odd removal of choice? If my very first character had been this kind of person, not much of it would make much sense. Besides that, the game never seems to make anything seem urgent. I mean, instead of going around killing dragons, and preventing you know who from doing you know what, I'm happily ignoring that and leveling from 1-50+. I mean really, how long do you realistically think it would take someone to go from novice to master? Years and years, not a matter of days.

You could rationalize that you are killing the dragons merely to increase your own power. Killing dragons allows you to take their souls, which you need to unlock shouts, and their bones/scales for armor. You could also complete the storylines in a way that creates an acceptable narrative for your character. Do the main quest, then have a fall from grace, such as becoming a vampire or murdering an innocent. Or ypu could ignore the main quest, finish the guild/DB and the redeem yourself with the main quest.

You might want to start by defining personal goals that your character wants to achieve. Does he/she want to be rich? Do they want the personal freedom to murder indiscriminately, or do they want to achieve certain effects with their murders? What side in the civil war will ultimately benefit your character (in regards to your character's personal wants and needs) in the long run? Does your character want to simply be totally selfish, or completely, diabolically evil? Or a mix of both? Or, hell, does your character want to do some good, so long as they can serve themselves whilst doing good? The answers to these questions will hopefully help you guide yourself through the myriad of choices you can make in the game that can or could benefit your character.

For here-and-now moments, ask yourself: will this benefit my character in the short-term, the long-term, both, or not at all? The first answer should be obvious, and should be acted upon unless the long-term benefit to your character is negligible or goes against your characters desires. The long-term choice is harder to make and act upon if it's something you know will not benefit your character until much later into the game, or not at all within the bounds of the game. You could make a choice that could theoretically benefit your character beyond the scope of Skyrim, wihch would be roleplaying at it's purest, since it's essentially a decision made to fit the story you have laid out in your head for your character. If a decision benefits both the short-term and long-term, it's a no-brainer, as is the result of a choice not benefiting your character at all.

It would also help you to decide if you want to maximize your character's abilities, skills, perks, and gear, or if you want to focus purely on the story. I think if you do the latter, the former will come naturally to your character. Focusing on the former alone can be fun in a gameplay sense, but perhaps not in a storytelling sense. Whatever you choose to do, make sure and make it enjoyable for you, and not just your character!

Have fun!

Yeah, the option's not there. You can't also do it because of text choices. I'm trying to Roleplay an Imperial Assassin who only does jobs for money and kills for pleasure yet all I can choose when asked to bring something or something my only choice is " I want to help you because I am a good person" (that's pretty much the dialogue choices except for a few that include like "what's the reward" or something like that. It's like you can only be a damn goody-two shoes..

I am currently carrying this out atm. I joined both the DB and Thieves guild, and am going out drinking and killing people in a "drunken rage". It's quite fun, actually.

What kind of assassin openly states "Oh btw, I'm a evil dude" lol, if it was me I'd definitely act all polite so they wouldn't expect it when I jab my dagger through their gullet

Right, "redeem myself". Problem is, my character is not looking for redemption, so I'd basically have to quit playing after I've done most things other than the dragon attacks and leave it at that. I can do this since I've already played the game and know the plot, but if I was trying to do this as a first time playthrough it would literally be impossible. Without having played it or read spoilers, you have no idea when the dragon attacks are triggered or the chain of events that follow. I want to play a selfish jerk of a character, one that's almost completely chaotic, but I would not be sticking to that alignment if I did any of the main quest.

Even if I did decide that I wanted to redeem myself, it really would have to be after I've done everything else, because it makes absolutely no sense to be doing contracts for any of the random guilds if the world is about to end. You'd think you would be able to sort out your priorities a little better.

I guess my main issue is just the lack of any real time scale. The game is "open world" and allows you to do things in whatever order. But it contradicts the entire plotline when you play that way.

Keep all the sweetrolls to yourself. That is the epitome of selfishness.

Argonian Anarchistic Assassin. The three A's. Let's begin...

You're caught in a province thousands of miles from your origins, between an Empire that allowed your people to be enslaved and a group of racist nationalists that want the land for themselves and their primitive prejudices. Nearly executed due to a lack of bloody paperwork by the former, you are determined not to be identified again.

You stick to the shadows because it's how you stay alive - you hunt people, and even dragons, as an exercise in your power, and as a means of expanding it. With little respect for your people from those in power, there is no point in bonding racially with other Argonians. They are picked on relentlessly, and as Madesi of Riften proves by sleeping in Beggar's Row, there is little defence for an Argonian other than his ability to blend in. Respect does not count for much.

The Thieves Guild and Dark Brotherhood are opportunities to do just that. The former is your means of wealth - the opportunity to open up impersonal contacts across Skyrim through which your invisible antics can become profitable, and access to stealth-orientated gear that makes you that much better at what you do. As you contribute to the organisation, so it helps you. The Dark Brotherhood is for the quenching of more sinister desires - either join their ranks as another shadow and reap the rewards, or take offence at the presence of a group trying to do what you do so well, and kill them when you have the chance.

From there, it's up to you. There are countless groups of bandits, idiotic amateurs, who cannot hold a candle to your finesse and skill. There are Daedra of stealth, and murder, and violence, and treachery, and of the hunt, that all demand a champion. The snow and the shadows are what you make of them, my friend. Happy hunting.

I avoided the main quest line until I played through the thieves' guild questline; then I had the character redeem himself during the main questline which I picked up really late, like level 28. I was thinking that I might do something similar if I wanted to do a Dark Brotherhood later. Perhaps getting bitten by a vampire turns him into a monster. Once I reported to Whiterun and got the Bleak Falls Barrow Quest, I decided my character wasn't interested in helping out "the man" and trecked to Riften to join the Thieves' Guild.

That is the one thing that drives me nuts about Bethesda: they create this awesome sandbox world then try to railroad you immediately into a linear main quest. I would like it so much more if the main quest would be put off until the character reached a certain level. You're right though, it doesn't "feel" right from a roleplay perspective to play the main quest as anything but a hero type.

I wouldn't let them know I'm an Assassin, but I sure as hell wouldn't be polite either. Selfish and Sarcastic responses are what I'm looking for here. And also some that I'm letting them know I don't care for them I just care for the money they will owe me when i retrieve their sword/ring/necklace/whatever from that old tomb next to the city.

Edit: To add more:

Instead all I get are " I'll be glad to help you with everything you need! Please, tell me your orders! I'll go and carry them immediately.

I'm playing a character that is a bit like a Dr. Doom origin story, a cross between crafting (smithing/enchanting/alchemy), magic, and combat, plus I'm a criminal, so I steal whatever I want but I don't go around killing people willy-nilly. If they get in my way, sure, the fools have it coming, but no rampages for me. I actually protect the farmers and 'small folk' from bandits and other predators because, frankly, I consider them my (future) property and killing them is depleting my (future) wealth. I, and my loyal henchman, Lydia, complete quests to destroy my potential rivals, loot their corpses, and impress the peasants with our superior might. The dragons, of course, must all be slaughtered to ensure my eternal glory. People can call me a hero if they want. It will just make it easier to bend them to my will when I take over Skyrim.

Thats how I play a selfish character. I haven't finished the main quest or the major faction quests, so I don't know how it will all work out, but so far I've been able to rationalize pretty much anything. The trick is to add an invisible sneer to every dialogue option.