[Huinesoron]

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.
6. N - 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.
14. O - 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.]

Correct, Pervinca! To be honest I don't think any of this was ever filmed, though Old Man Willow gets sort of used in Fangorn. (I was surprised to find no mention of the Old Took in the script, though!)

Neither Udun nor Oliphaunt (though I considered it); you're right to be looking at songs for #11, while #2 consists of a straight and a cryptic clue.

hS