I know they don't get much love in the game, but I would want to be a monk. I think their abilities are really cool, and even if they don't come through mechanically in the game, I think in real life it would be awesome to be able to run super fast and jump super far. You'd be a superhero, but it would just be your inner skill not some magical (Temporary or dispellable) effect. I would imagine that I would look a lot like I do now. Long hair, thin but athletic build, tall and never concerned with fashion.
I am an engineer by training and inclination. I love the process of designing and creating things, especially things that benefit others, and have a strong interest in robotics.
With that in mind, I have to go with being an Artificer. Start up my own business producing magic items, work my way up to managing an army of constructs, some designed for personal benefit/defense, others wrights working to produce both magical and mundane things for sale of my own design, along with taking the principle work burden off of myself so other pursuits can be pursued.
I am definitely chaotic, and probably tend towards good or neutral. I only follow rules when it benefits me and generally expect others to behave in their own self-interest (Just look at our president). It makes it easier to accept that life isn't so bad when you realize that society is just a construct to tell us how to interact with each other and most people disregard it when it doesn't suit them. I do want to better the community I live in, so I think I fall into good on that spectrum, but I rarely act on those intentions. I usually let it fall to somebody else. I guess it comes down to whether you assign an aligment based on ideals or actions. According to my ideals I am CG, but my actions probably say more CN.
I would say I'm Neutral Good. It's important for me to help others in any way I can. I'm more about good being done than the law being followed. I don't frequently disobey the law though, knowing the possible consequences. I live within the framework of our established society but feel that the spirit of the law is more important than the letter of the law.
So, my alignment is complicated. Having been in the Army and in the types of units I was in I tend to do what is needed to succeed. I guess you could say I have a Machiavellian outlook on life. So, the philosophical question of the day is, does the end justify the means? I think the answer is yes, but only to a limited degree. Saying that, I guess I'm NG to TN with a tendency to do whatever is needed in the cause of good.