What is this 3.5 guy's alignment?

[Laraqua]

Basically, I have an NPC whom a PC (actually the NPC's son) is trying to convert to good (as in Exalted Deeds conversion) in a Vile Campaign. I now need to suss out his alignment and it's trickier than I thought. It's rather complex, so bear with me...

He is a 1st level bard, 7th level cleric of a Trickster God (my own invention), who has a rather rough history. Due to the treatment given to him by his family, and a rather tragic upbringing, he is grown into a bitter and hateful young man who covers his misery and creates conspiracies through the persona of a cad and a fop. Think theatrical big gestures, dry wit, and a sardonic way of talking. His consuming passion is to tear down the fiendish blooded noble house that he was born into. He does this in three ways:

1) By revealing just how evil the house is to the world at large. He does this as a debauched fop who does this by throwing disturbing parties where he underlines how creepy his family is to the other nobility through artistic decor (wax figures, preserved bodies, skulls, candles of human fat), tweaking people's lusts to cause falling outs between various people (he has access to spells from the Book of Erotic Family), and being a relatively open drug addict and dealer.

2) By following a path of his own self-destruction. This is a sub-conscious drive where he half rebels through drug abuse, alcoholism, self-injure, and by sudden acts of malice where he burns bridges. He once even convinced his own son (an orphan who's been convinced that his uncle is his father) that his parents were brother and sister (false), that he was born of a rape (half-true), and that his dead mother has risen a horrible, murderous vampire out for his blood. He even convinced the kid to stick his hand into holy water (knowing it would scald him) in order to have the kid prove a point to him.

3) By enacting a conspiracy to tear the family down from within, setting up a situation of cross-and-double-cross where he can get close enough to a few key members and arrange for their destruction through treachery and deceit. He's even got the family convinced he's an arcane caster and not a divine caster through the judicious choice of spells. Of course, this conspiracy is more a case of intuition and taking advantage of changing circumstances than a well-thought-out long-term plan.

While not a fan of torture, he does use it to a small extent (nothing too meticulous, more a few broken fingers) when his enchantments don't work on people. He twists other people's minds through illusions and enchantments to suit himself and uses other people to his advantage - even breaking healthy marriages to suit himself. When enraged, he acts out through back hands and toppled furniture and is not above slapping children across the face.

On the other hand, he used himself as bait to lure a rapist away from his son; slays undead and monsters to keep the general populace safe; will lie to save another; abhors rape; will generally risk his own life and plans to save an innocent despite himself; absent-mindedly tosses coins to beggars; and is wracked with guilt (which he largely doesn't show).

So ... for those few who've managed to read through all that, I thank you. Any ideas what his alignment would be?

[Argyle_Warrior]

What a messed up little man . . .

I think this is a perfect example of why the alignment system is a guideline and imperfect.

However, as he needs a classification for your purpose, he is either Chaotic Neutral or Chaotic Evil. The real question is does he mess with people simply to fulfill his own ends, or does he do it for the sake of evil? Breaking up marriages to suit his needs is a Chaotic Neutral act (marriage is an institution with no good nor evil implications). Forcing spouses to commit adultery because he thinks it is funny would be Chaotic Evil.

He's unquestionably Chaotic because his entire being is devoted to destroying the status quo and ruining the establishment (his family). Although his methods are questionable, and he's by no means a good person, he does have good qualities and could easily "excuse" his evil ways with his "good" cause, which would make it neutral (for now). If he ENJOYS what he does and how he does it, or begins to as a plot development, he's EVIL. If he regrets what he does but sees it as his only way to achieve his goal, he's neutral and already on the path to redemption.

[Laraqua]

Thanks. That's really helped me a lot. On one level he does enjoy himself when he does what he does, largely for the feelings of power it brings him and as an outlet for his bitterness and anger, but he also regrets what he justifies as necessary evil for the common good and is not beyond matyring himself for the cause where he can in order to deal with his own self-loathing. For example, he plays up all of his evil acts for all that it's worth to ensure that the innocent will avoid him when they can, and tends to target people for his little games who're stupid enough (rather than desperate enough - as he takes pity on those who HAVE to deal with him) to come to him through their own free will.

So, I'm supposing that makes him Chaotic Neutral. Good news for the player then as it'll make it a damn sight easier to convert him. Thanks for the advice!