Did you know everything important about your personality, morality and worldview can be defined into one of nine categories? It's true… at least if you're a Dungeons & Dragons character from the first to third editions. Not every tabletop role-player has been a a fan of D&D's Alignment system, which help players define their characters' behavior, but now that Wizards of the Coast is hard at work on D&D's fifth edition, I'd like to make an earnest plea for them to bring it back in its original, nine-aspect glory by showcasing the Alignments from best to worst.
Would you like to play 1) someone who is not bound by notions of good, evil and society, 2) is completely selfish, or 3) a dangerous lunatic? Then Chaotic Good is for you. Normally the alignment of the insane - which are always fun to play - Chaotic Neutral also allows players to essentially justify any action. Want to save the princess and return her to the king? Want to kill the princess in cold blood and wear her dress for the rest of the adventure? You're Chaotic Neutral, baby. You can do anything.
Newbies often think Lawful Good is the alignment of heroes, but experienced players know that true heroes are Neutral Good. They understand the law is only just as long as its made and enforced by good men, and aren't afraid to ignore it when the law is bad or outright evil. The evil king issues a royal command for you you to go kill the princess? Nuthin' doin'. These are the heroes who get stuff done.
As you might guess, Lawful Evil people try to commit their evil deeds though legal/socially acceptable means, which can be a pretty interesting dichotomy. These people can be evil nobles and merchants, or they can simply be selfish, looking for ways to bend the laws to their own gain. The best part about Lawful Evil characters is that played subtly enough, these characters can appear like heroes to other characters, which is always fun to play. But it's even more fun when the characters also think they're heroes.
Much like Neutral Good is the alignment of true heroes, Neutral Evil is the alignment of true villains. Any villain worth his/her weight in captured princesses will choose this alignment, as it offers the maximum opportunity for evil, because they aren't hindered by the law or their desire to cause mayhem. They say villains are more fun than heroes, so you may be wondering about why Neutral Evil is ranked lower than Neutral Good. That's because, in my opinion, since D&D is a game based essentially on murdering every single thing you meet and stealing their shit, trying to be a hero in the world of D&D Is actually the more interesting option.
When I was a young D&D player, I thought Lawful Neutral was the most boring alignment. Then I read the Games of Thrones books and met Stannis Baratheon. There's something very compelling about a dude who follows the law no matter how good/bad/insane the law is, with no regard for others or even himself. It might make for some (excitedly) awkward moments, like when that evil king orders the party to do something evil, like execute that princess. Sure, the rest of the party may be appalled, but Lawful Neutral ain't care. Someone get him an axe.
If heroes are Neutral Good, what does that make those who are Lawful Good? Paladins, i.e. assholes. Paladins and other stick-up-their-ass good guys try to do good within the system, and are invariably limited by it, and irritate every single other player with their goodie-goodie bullshit. If that evil king tells a paladin to murder the innocent princess, he won't do it, but he'll agonize over the decision for two whole gaming sessions. They're just just annoying, man.
If Lawful Good is the most boring of hero alignments, Chaotic Evil is obviously the most boring of villain alignments. Wha? This person is evil and they don't play by the rules? Someone get me some Goggles of Minute Seeing to put on, so they can pop off my face in shock. The only time that Chaotic Evil can be interesting is when characters put committing evil above their own well-being, especially if they can't help themselves. It's one thing to purposefully try to drive a wagon over a bunny, but it's another to willingly drive that wagon off a cliff trying to do the same thing.
Do you want to be a tortured anti-hero? Well, get in line with every other middle-school to high-school-aged D&D player ever. Look, I know Wolverine seems really cool when you graduate from sixth grade, but you're quickly going to realize that 9/10ths of other players think the same thing, and that basically every single other character you meet who isn't outright evil will probably be chaotic good, too (and many of them will be playing up the tortured anti-hero bullshit, too). It's not that Chaotic Good is bad, per se (you know what I mean) but it's also pretty much the default alignment of the D&D world. When people don't care about the role part of role-playing, they invariably end up Chaotic Good.
There are only two alignments that cannot be trusted: Chaotic Evil and True Neutral. Chaotic Evil characters are crazy evil, so what's True Neutral's excuse? Only the dumb would be so invested in the balance between good, evil, law and chaos that they feel they have to maintain it, which is why True Neutral is the preferred alignment of Druids, a.k.a. dipshits. Look, if there's a chance you may decide that letting bugbears kill everyone in the party is necessary in the natural order of things, then there's a chance I'm going to slit your character's throat in his sleep. Hell, at least with Chaotic Evil characters you know where you stand.