Standard caveat: Alignment discussion is an ongoing, unending battlefield morass of discussion and debate and argument. (And, I would argue, it’s been purposefully set up that way.) You can and should develop your own perspectives on this subject, and if you disagree with what I say here, that’s cool. By all means, let’s talk about it.
Chaotic Good people run the gamut from political revolutionaries struggling against an oppressive regime to good guys who don’t much care about the rules to rugged individualists soaked in beneficence. They consider the good of people more important than the actual law, which they view with distrust or contempt. They’re often impulsive and disorganized, trusting instinct over planning, and often never run the same con or strategy twice.
Chaotic Good individuals are susceptible to their anarchic influences, and can easily end up skirting that moral line. Chaotic Good adventurers tend to be good at improvisation when their loose plans inevitably fall apart, and they consider adaptation more important than strictures. They tend to run from responsibility or authority, though sometimes they embrace it in the end because it’s the right thing to do. Their loyalty is to a cause, not to an authority.
Examples: Aragorn is Chaotic Good. Robin Hood is Chaotic Good. Zorro is Chaotic Good. Malcolm Reynolds is Chaotic Good. The Dread Pirate Roberts is Chaotic Good. Elminster is Chaotic Good. Garin Ravalis (from the World of Ruin series) is Chaotic Good.
Chaotic Neutral revels in chaos and disorder. A Chaotic Neutral person is unpredictable in the extreme and rarely repeats the same stratagem–if they even see it as strategy. They act on their whims and feelings and rarely edit themselves. They rely on themselves alone, take people by surprise, and often take pride in doing both. A Chaotic Neutral person generally has no use for law or authority and make go out of their way to frustrate the efforts of lawful characters and institutions.
A Chaotic Neutral person is marked by a streak of amorality–rarely do they side with a good cause, nor do they let the evil of an action make them hesitate. They need more compelling reasons than “it’s the right thing to do” to prompt them to action. However, despite its reputation, Chaotic Neutral isn’t intended to be carte blanche for “do whatever you want, whenever you want.” Yes, there is that, but Chaotic Neutral goes further. It is a lifelong commitment to defying expectation, trusting your instinct, and undermining expectations.
Examples: V from V for Vendetta is Chaotic Neutral. Deadpool is Chaotic Neutral. Harley Quinn is Chaotic Neutral. Catwoman is Chaotic Neutral. Ilira “The Fox-at-Twilight” Nathalan is Chaotic Neutral. Mask (from the World of Ruin series) is Chaotic Neutral.
Chaotic Evil is our classic sense of what evil is–unpredictable, monstrously bad–and that seems to be intentional in the setup of the nine alignments. In truth, though, it’s no more or less evil than any other evil alignment–just often more obvious about it. This goes to how we pathologize mental illness, and we often make our villains out to be “crazy” and “chaotic,” but that’s another discussion for another time.
Just as Lawful Good isn’t necessarily Lawful Stupid, neither is Chaotic Evil necessarily Chaotic Stupid. We’re all familiar with roving, mad monsters that sow destruction and chaos for pleasure, but one can be quite a bit more subtle. There’s nothing about the alignment that says you have to be loud and bombastic. As long as you work toward the common ill, sow confusion and revel in setting people off their ease, pride yourself on being unpredictable and only serve your own interests, odds are you’re Chaotic Evil.
Examples: The Joker is Chaotic Evil. The drow, orcs, and many monsters are Chaotic Evil. Demons are Chaotic Evil. Ramsay Bolton is Chaotic Evil. Lilten Dlardrageth is Chaotic Evil (though he’s urbane about it). Fayne is Chaotic Evil, though she evolves to be more Neutral over time. Alistra Ravalis (from the World of Ruin series) is Chaotic Evil.