Okay, let's take this in order:
14 is indeed ORALD, for pretty much the reasons you said. 'Singular' indicates that you need to lose the S from Ladros.
11 is not Mithrandir; I don't know whether it shows up in dialogue, but the haunting Elvish lament in Lorien does include this name. The character you need for this clue shows up
with a name in earlier parts of the Legendarium, and
without a name in a song. Except in the movies, where he doesn't appear at all.
2 is not Underhill. The first half of this clue is a description of the thing, the second half can be translated to find the precise name. (As
Pervinca says, 'Underhill' does appear in the movies - I would've much preferred to use it, honestly!)
9 is not Olog(-hai) or Old Stone Troll. You're on the right track with 'not new', but you need to be looking for a different use of the word 'race'. ('Not safe' is the fairly vague straight clue.)
13 is not Limpė. The answer here is not particularly wicked - in fact, it's a common English word. It's the way of getting there that I consider truly malevolent. ^_^
(Limpė = lemsip is my new headcanon now.)
Quote:
C onspiracy - If three (3) is company, then what is five (4)?
2. U - Twixt dark below and dark above, below & between.
T hree Dwarves - + 60, -10, still stepping out of the same door.
T ower Hills - A place of first meetings, lingering glances, and (nearly) last farewells.
I mrahil - Twenty-second in the line.
N ob - A bit sweet, but backward, and if I gave a direct clue it would probably be crude.
G lorfindel - Elvish ... and a trio of Beornings.
R ed Arrow - Gondor calls, "The flaming cursor!"
9. O - Not new, not two, not race, not safe.
O ld Man Willow - They could make almost a Hobbit sequel, but Warwick is necessary first.
11. M - With a name, he's a stalker above all others; without his name, sing who he is.
F atty Bolger - Left behind; his namesake is on the Barrow-downs though.
13. L - Scrambled in an anagram: retained in the taproom.
O rald - Singular, lost in Ladros, in a house by the river.
O ld Took - Bilbo passed, and the Age removed
R angers of the North - Before they were grey, they served still.
[Theme: Things not in the Jackson movies.]
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