I want to talk about Legolas and singing. (Hang in there, because it starts out a little silly but turns meaningful.)
How many times do you think he just broke off into song during the Fellowship's quest? Well, one time he's like, "Let me sing you this song about Nimrodel!" He also sings to himself in the middle of the night when he's on watch. When the Three Hunters reunited with Merry and Pippin, they relax and smoke their pipes - except for Legolas, who lounges next to them, looking at the sky and singing softly to himself.
He sings to the horse of Rohan when it freaks out about the Paths of the Dead. He stops in the middle of recounting a story to the Hobbits, breaking off to sing a song about the lands they passed through, which feature in the account he's telling. When he goes to see Merry and Pippin in Minas Tirith, people watch curiously, not only because it was odd to see an Elf and Dwarf at ease with one another, but also "Legolas was fair of face beyond the measure of Men, and he sang an elven-song in a clear voice as he walked in the morning...." And then later he mentions that he hopes to bring some of his people to the region - but he gets distracted thinking about the river, which leads to the sea, and he wanders off singing to himself of the sea.
We know singing is important to all Elves, but it seems to me that Legolas randomly sings more than maybe the average Elf does. Maybe it's just because we get to see so much of him compared to some of the other Elves - but either way, I like to think this is his way of keeping his hope up.
Legolas is from Mirkwood, and not only that, he's a prince. He possibly remembers when his home was still called Greenwood, before the shadow of Sauron came over it. Being that Mirkwood was one of the last Elven realms preserved in Middle Earth, it must have grieved and angered the inhabitants to watch this evil befall. Years were spent trying to fight back the Shadow over Mirkwood. It stands to reason that Legolas had a significant role in that. No doubt he took this very personally, trying to defend and preserve his people and their beautiful realm. At times it seemed that the Shadow was driven back, only to return again. Among the Wise, it was highly suspected that Sauron would make another comeback and the age of the Elves in Middle Earth would be over.
And yet Legolas keeps singing. He sings folk songs from his people, he sings of beautiful lands far and wide, of ancient heroes who gained renown fighting the enemy. Maybe he even made his own songs, too. And in the face of the darkness, when it seemed the Shadow would swallow everything up, the only thing he could do to keep his courage was to keep singing. I'd like to think that's part of why he's developed the habit of just singing to himself sometimes. That, and the fact that he just likes to sing and express himself in song, and he possesses a buoyant spirit. But where did that come from? Is it just a personality trait, or something more, something fine-tuned in the Shadows of Mirkwood in defiance of Sauron?
When Legolas sings, it comes from a hard-bought hope cultivated by years of trial. Greenwood may become Mirkwood, but the Greenleaf is still green, and he's not about to let that change, though it takes him to a battle against all odds at the Black Gate itself. He, too, sings to remind himself that the Shadow is only a passing thing. It cannot vanquish the joy and hope and wonder at the beautiful things of the world that overflows at random moments. And that's why we love him, silly moments and all.
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