Most Tragic Tolkien's Legendarium CharactersJust as there was song, cheer and merriment in Middle-earth, there was also sorrow, hopelessness and unnumbered tears shed. Due to the nature of this list, spoilers are abundant.
The Top Ten
This man could have achieved great things if he wasn't cursed, and even though he tried to do good, Morgoth's malice and Glaurung's sadism put a stop to that. Considered to be the greatest of mortal Men in the Elder Days. - FrozenHatingPokefan
There is even a beautiful ballad by Blind Guardian about Túrin titled Harvest of Sorrow. Túrin mourns the loss of his sister Niënor.
By the way most of the characters on this list were portrayed by Blind Guardian in their songs (I made a list you can check out - Top 10 Blind Guardian Songs Inspired by J.R.R. Tolkien) - Metal_Treasure
Just a normal hobbit until he found the Ring of Power. You know the rest. - FrozenHatingPokefan
Went through a lot of pain, desipte being a complete @ss with an ego the size of the universe. - FrozenHatingPokefan
There are 2 songs by Blind Guardian about Fëanor - Nightfall, The Curse of Feanor - Metal_Treasure
He was a great warrior who was renowned in Beleriand and had a lovely wife and kingdom. Then the Battle of Unnumbered Tears happened. He fought unto a bitter end, and hen was taken into Angband by Orcs, and he refused to tell Morgoth the location of Gondolin, so Morgoth chained him to a chair and cursed his family, forcing him to watch their suffering. - FrozenHatingPokefan
Turin's sister. Went to live in Doriath with her mother, and grew in a beautiful young woman. Her mother, Morwen, found out Turin was a warrior in Nargothrond, they went there, but it had already fallen and Nienor was placed in an amnesiac trance by the dragon Glaurung. - FrozenHatingPokefan
Was a mortal man who fell in love with Luthien, the most beautiful elf-maiden in Arda. They went on a quest to infiltrate Angband and steal a Silmaril, so they could marry, but things went awry after that... - FrozenHatingPokefan
See above. She had a better life than her husband, Beren, but went through a lot alongside him so they could be together. - FrozenHatingPokefan
Poor bastard. He genuinely cared for and loved Niniel, but the fact that Niniel was cursed and she unknowingly married her brother, who was also cursed, meant that things would not end well. - FrozenHatingPokefan
Kinda hard to feel sorry for him after all the evil things he did, but if you couldn't sing what you wanted, then you'd be pretty angry too. - FrozenHatingPokefan
Similar situation to Luthien. - FrozenHatingPokefan
His death was very tragic - Cattima