Seems Like Someone's Rooting for the Wrong Side

[The Squatter of Amon Rûdh]

The original conception for the Silmarillion material in the Book of Lost Tales was that Eriol heard the tales directly from various Elves. Later this changed so that the legends were written down by Eriol (eventually Ælfwine) at Tavrobel in Tol Eressëa from the Golden Book of Tavrobel, which is a history composed by the Elda Pengoloð. Later conceptions of transmission are unclear, but The Silmarillion as published makes no mention of its fictional authorship and I don't recall anything Tolkien wrote that contradicts the idea that The Silmarillion is a collection of records kept by the Eldar (more specifically the Noldor).

This being the case, anyone with any sort of historical training will be able to postulate a significant amount of bias in favour of the Elves in most of the material on which we base our judgement. LR is the Hobbit perspective, with interpolations from human and Elvish records; the Silmarillion is the Elvish perspective received second-hand through Eriol/Ælfwine (via Old English), or Bilbo Baggins' Translations from the Elvish (via Westron), whichever version you prefer.

However, these aren't historical documents. Tolkien knew both sides of the argument, and in fact he presents Morgoth and Sauron's views at several points in HoME and LR, not to mention those of the Orcs through their reported speech. He demonstrates that the unrepresented side is arrogant, power-hungry, destructive, cruel and greedy. Why, then, do people like them?

As far as I can see, there are several reasons. Firstly and most importantly, the bad guys get to do as they please. Everyone else has to obey the rules, or at least take some account of others when making decisions, but evil characters, being completely egocentric, are allowed to ride roughshod over everyone to get what they want. Those of us who do consider others might well find it therapeutic occasionally to step into the shoes of someone who doesn't.

Added to that there's the obsession with rebellion. If anything, the modern era is one of social disobedience and non-conformism, so that we're practically raised to support anyone who doesn't obey the rules. If the rules are that we all share things and respect one another we want to see someone who lies, cheats and steals. Tolkien would probably have said that this is our fallen nature speaking, attracting us to the selfish, degraded and base; but very few people still think as he did.

Finally there's irony. Above all rhetorical techniques, our age has made irony its own. One of the reasons why LR is so unpopular is that it contains virtually none: it takes itself absolutely seriously, and the current fashion is for detached amusement. The ironic approach to LR and The Silmarillion is to try to write a revisionist history of Arda, or at least to identify with one of the characters presented to us as irredeemably evil. Then again, perhaps Saucepan is right and the admirable quality is that the evil characters are effective. Their methods work in the majority of situations, and a utilitarian mind might think that therefore theirs is the course to take.

Having said that, this is all invented. It's not real. I hope that none of us would choose to follow Morgoth or Sauron if they were real physical presences, that is without being somehow duped or coerced. Morgoth, Sauron, Saruman, Grima and Shelob, and all of the other evil characters of Arda are just figments of Tolkien's imagination, and supporting one of them won't change the world one iota. It won't even change Middle-earth, because that story has already been written and the one person capable of re-writing it is dead. In that sense, then, this argument has no bearing on reality and is inherently pointless. If we were discussing why people choose evil at all, well that would be the sort of relevant philosophical discussion that the last century prompted many more people than us to consider, and Tolkien was not the least of them. It's possible that he would have regarded sympathy with his evil characters as symptomatic of humanity's spiritual weakness, or he may possibly have noted that those who can imagine being the Witch-king or Sauron are probably in less spiritual danger than those who simply dream of making the world a better place for people whether they like it or not. Sauron himself fell because he wanted to order the world and improve it, so he must always have imagined himself to be among the virtuous until he reached a point where good and evil were no longer important concepts for him.

Personally I don't see any harm in dressing up as the Witch-king or imagining oneself to be an Orc, other than a general discomfort with taking fandom that far at all. Provided that we do the right thing when it matters (in real life), we can do whatever we like in our imaginations. Importantly, if it's such a bad thing to identify with Tolkien's villains, then what can we say about the person who wrote them?