The Silmarillion/YMMV

Canon Sue: Lúthien. She has all the classic elements of this (great power, incredibly beautiful, Rebellious Princess, accomplishes a deed no one else ever managed, idealized representation of a real person, etc.), but Tolkien makes it work.
- The book's mythical style is probably what makes it work. Old stories are ridden by Larger Than Life figures that cultures associate themselves with. Luthien comes as this, and it is pretty clear the stories are painting her as some sort of great example of how to behave.
Complete Monster:
- Morgoth is this world's equivalent of Satan, so explaining why he is this trope would be just redundant.
- Glaurung is possibly one as well, due to his utterly ruthless and twisted manipulation of Túrin and Nienor. At the same time, he pulls it all off incredibly slickly and with awesome dialogue, so Your Mileage May Vary whether he is this trope, Evilly Affable, or Magnificent Bastard.
  - Do note that none of these tropes are mutually exclusive, though.
Draco in Leather Pants:
- Fëanor. So, so much.
- Maeglin gets it too, though not as much.
- So does Morgoth. Apparently, he looks like The Woobie for some. There is even a major Russian fanfic, The Black Book Of Arda, that even was piratey published as a book, that retells Silm from Woobie Melkor's viewpoint.
Ensemble Darkhorse: Nerdanel. The amount of fanfiction and fanart she has received is in no proportion to the very limited pagetime she has in the published Silmarillion.
Iron Woobie: Túrin Turambar.
Magnificent Bastard:
- Sauron, especially during the fall of Númenórë. Fëanor also has shades of this.
- Probably Glaurung too as noted above, though it is hard to tell whether he is a Chessmaster in his machinations against Túrin, or merely the instrument of Morgoth's curse.
Moral Event Horizon:
- Fëanor
  - He crosses it when he leads a shocking massacre of the Elves who dared refuse him use of their ships. Then he crosses it again when he sails to Middle-earth with his most loyal followers, then burns the ships so the majority have to travel through the freezing far North, an ordeal where many of them die.
  - This has been the topic of endless debate in Tolkien fandom. Basically, you can argue that the massacre was unintended (Fëanor never gave the order to kill anyone), and those left behind after the ships burned could just go back to Valinor, since they were unhappy with the whole Flight thing. Your Mileage May Vary.
- Morgoth crosses this in the eyes of the Elves when he kills Finwë and steals the Silmarils. The moment that hits home just how evil this guy is, though, has to be the cursing of Húrin's family. Túrin's life was just one tragedy after the other, ending with his suicide. This is made even worse when you realize that all the misery was really caused by nothing more than Morgoth's temper-tantrum. Especially since Túrin wasn't even the one that provoked Morgoth; that honour goes to Túrin's dad. Túrin's miserable life is merely a decades-long torture inflicted on Húrin as punishment for his defiance.
Nightmare Fuel.
- MORGOTH. The Satan of Arda, Morgoth engaged in Mind Rape without even having to think about it, and the only sort of pleasure he could experience came from horribly torturing and corrupting Elves and Men. In-universe, lesser Ainur were driven to insanity by his eyes.
- Ungoliant.
Older Than They Think: "Earendel" is an old Northern European name for a god or a star or something along those lines. It seems to be one of those words that stick in peoples' heads : names like Earendel/ Horwendill crop up in the oddest places - James Branch Cabell and John Fowles's The Magus, and such.
Straw Man Has a Point: Eöl, being one of the Dark Elves who chose to remain behind in Middle-Earth rather than sail West to the Valar, hated Fëanor and the Noldor who fled Valinor and pretty much invaded Middle-Earth, even going so far as to kill Elves of Eöl's kin. Thus he refuses to cooperate with Gondolin or the other Noldor states, and allies with the Dwarves and (presumably) the Green and other Dark Elves.
Tear Jerker:
- When Eärendil wanders through the streets of deserted Valimar and the dust of the gemstones covers his feet. Note that this was originally supposed to be much more of a Tear Jerker, as Eärendil had arrived too late and the Elves had already left for Middle-earth; Tolkien changed it to make it a bit less tragic, with the Elves only being away at a festival and soon returning.
- Túrin Turambar--pretty much his whole life
The Woobie:
- Túrin Turambar, also Jerkass Woobie.
- Maglor.
- Gwindor.
- Jerkass Woobie: Fëanor, so much. He gets a lot of sympathy and apologetic fans for someone whose actions directly set in motion a series of events that led to so much suffering and death, including genocide and a world-shattering cataclysm. Possibly because, despite being a jerkass of truly epic proportions, he was also a total badass.
- Stoic Woobie: Maedhros

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