While I do agree with all these choices, I have to choose Turambar, mostly because while Gollum and Denethor were infected by artifacts such as the Ring and Palantir, Turin himself seems to be more relatable as a whole, since we, like him, can lose ourselves in our sense of pride, always listening to the voice inside us that tells us we are weak lest we do this thing. I would say Turin is the best choice above all. For like him, we struggle, we strive to be better. To attain victory in a cruel world. And deep down, we want to be better, we want to let go of our anger, yet we seem unable to. Whether for pride or something else, I cannot say.

Sorry about this. Just wanted to share. Have a great day, y'all.

Sméagol but Denethors is tragic because he loses his wife to the shadow of Mordor and later his son like cmon.

Also Turins because the poor guy felt that he needed to kill himself.

All True. No One Person's suffering is greater than the other.

I felt so bad for Smeagol, he has it really bad, but Hurin did not deserve to have that happen to him. Frodo's had a large majority of his life be great, and ended up spending the few small years left in the undying lands. Yes, in terrible physical and mental condition from his quest, and he died young: at most 60. But, though coming perhaps nearly a century sooner, his death did come to him as a happy Hobbit. That's more that can be said for Smeagol or Hurin, who had been tortured heavily.

The whole story of Túrin Turambar is BY FAR the most pitiful and sad. Loses his father in the Battle of Unnumbered Tears, sent away to Doriath by his mother, accidentally murders Orgof in Thingol’s court, and goes on the run believing himself to be an outlaw. He then gets captured and tortured by Orcs, his long time dear friend Beleg saves him, but in fear he slays Beleg by mistake. Finally he gets to Nargothrond which gets absolutely decimated by Glómund the Dragon. Afterward he takes up a nomadic life style, finds Nienor, and falls in love with her, completely unaware that she is his long lost sister. Túrin then sets out to slay the Dragon, and in the end he prevails, but is wounded. Nienor finds Túrin, and Glómund, who restores her memory. Realizing that Túrin is her brother, Nienor casts herself over the nearby waterfall. Túrin, when he comes to, learns of Nienor’s fate and slays himself with his own sword………….. If THAT is not pitiful, I don’t know what is.

Glómund?

In the History of Middle Earth Vol. I, Part IV: The Shaping of Middle-Earth, the Dragon’s name is Glómund. In the final published edition of The Silmarillion he goes by the name Glaurung.

Don't use pre-canon names... there are many and will just confuse people.

Middle Earth Shadow dragons as well as a cannon

@Fandyllic this is literally a Wiki of Tolkien’s entire legendarium… it is a place to discuss ALL of the canon “pre-“ or “post-“. If you find yourself getting confused by a simple name change, then maybe indulging in a fictional universe of this magnitude isn’t for you.