- 2nd edition Player's Handbook
Chaotic Good was traditionally my favourite alignment; in fact I've probably even now still played more Chaotic Good characters than anything else, although these days I try to spread myself around a lot more. Actually in my experience it's the most popular of all the alignments, probably because it allows players to be Good without forcing them to be too Moralistic - and that's exactly what the majority of D&D players seem to want. It is after all the most fitting attitude for a traditional 'Good Guy Adventurer' type to take, representing unwillingness to conform and dislike for law, combined with a strong sense of right and wrong. It's the alignment of the rugged individualists of American and Australian legend who settled the 'wild' reaches of their respective continents (though let's mention the natives, thankyouverymuch) and wanted nothing but land, liberty and good neighbours - and those types happen to make very good Adventuring Heroes.
Of course, this overaccuntuates the Good while playing down the Chaos. The alignment could imply something more deliberate - for example good hearted but dyed-in-the-wool anarchists from the Parisian Left Bank, or non-racist libertarians shut away in rural Idaho, or anarcho-capitalists/individualist anarchists like Murray Rothbard or Lysander Spooner. That is, people who have a moral belief in disorder as the best way for everybody to live - and who see in government nothing but tyranny and evil. Though perhaps this is to overegg the Chaos at the expense of the Good: in the rhetoric of people like Rothbard, von Mises and McElroy it's often harder to discern the Goodness in amongst all the What's Best, which means something slightly different.
The ideal mix of course is the Han Solo or Robin Hood type; the man who stands against government brutality and defends freedom while never losing a sense of justice. But in a game in which revolt and guerilla warfare is not the aim, it can be difficult to make such characters work - we know why the Neutral Evil guy is after the dragon's treasure, but why would Han Solo give two hoots? Funding the rebellion perhaps, but how long does that last as a justification before it gets old?
In retrospect perhaps it is for the above reasons that the Rugged Individualist is usually the Chaotic Good character type of choice. Because Individualist Anarchism and robbing from the rich to give to the poor are all very well, but they don't seem like satisfactory reasons to pillage vast subterranean labyrinths.