Best Original Song - 2003

"The Scarlet Tide" from Cold Mountain sung by Alison Krauss

Movie Synopsis: A Confederate soldier deserts so he can come home to his love.

Does it appear in the movie (i.e. other than the end credits)? I don't know. I've seen this movie several times, but I think it's end credits.
Is it important to the plot? Mood.
Is it pleasing to the ear? C+. 

"You Will Be My Ain True Love" from Cold Mountain sung by Alison Krauss

Does it appear in the movie (i.e. other than the end credits)? Yes. 
Is it important to the plot? Mood as Inman is traveling?
Is it pleasing to the ear? B-.

"Into the West" from Lord of the Rings: Return of the King sung by Annie Lennox

Movie Synopsis: The former Fellowship of the Ring prepare for the final battle for Middle Earth, while Frodo and Sam approach Mount Doom to destroy the One Ring.

Does it appear in the movie (i.e. other than the end credits)? End credits and score.
Is it important to the plot? The lyrics are Tolkein's words, but...
Is it pleasing to the ear? B.

"A Kiss at the End of the Rainbow" from A Mighty Wind sung by Eugene Levy and Catherine O'Hara

Movie Synopsis: Mockumentary captures the reunion of 1960's folk trio the Folksmen as they prepare for a show at The Town Hall to memorialize a recently deceased concert promoter.

Does it appear in the movie (i.e. other than the end credits)? Yes.
Is it important to the plot? One of the band's songs.
Is it pleasing to the ear? B+ .

"Belleville Rendez-Vous" from The Triplets of Belleville

Movie Synopsis: When her grandson is kidnapped during the Tour de France, a woman and her dog team up with the Belleville Sisters--an aged song-and-dance team--to rescue him.

Does it appear in the movie (i.e. other than the end credits)? Yes.

Is it important to the plot? Character introduction.
Is it pleasing to the ear? C.

So what won?

"Into the West" from Lord of the Rings: The Return of the King

What would I have voted for? 

"A Kiss at the End of the Rainbow" from A Mighty Wind 

 

I like it best. So there.

Analysis

It was destiny that the end credits song from Return of the King would win, no matter what. That's just the way some things go. So, I opt to be a pill and vote for one of the true under dog songs. It's the prettiest. And it's actually important to its film. Plus, "Into the West" is such shit compared to "May It Be".