Best Original Song - 2001

"Until..." from Kate & Leopold sung by Sting 

Movie Synopsis: A duke from 1870's New York is transported to the present and falls in love with a modern businesswoman. 

Does it appear in the movie (i.e. other than the end credits)? End credits. 
Is it important to the plot? Not sure. 
Is it pleasing to the ear? B.

"May it Be" from Lord of the Rings: The Fellowship of the Ring sung by Enya

Movie Synopsis: A group of nine companions set out to destroy an evil ring.

Does it appear in the movie (i.e. other than the end credits)? End credits. 
Is it important to the plot? Not really... 
Is it pleasing to the ear? A.

"If I Didn't Have You" from Monsters, Inc. sung by Billy Crystal and John Goodman 

Movie Synopsis: Monsters generate their city's power by scaring children, but they are terribly afraid themselves of being contaminated by children, so when one enters Monstropolis, top scarer Sulley finds his world disrupted. 

Does it appear in the movie (i.e. other than the end credits)? End credits...I think. 
Is it important to the plot? Mike and Sulley talk about how much they like each other...ugh. 
Is it pleasing to the ear? D+.

"There You'll Be" from Pearl Harbor sung by Faith Hill 

Movie Synopsis: Two pilots and a nurse participate in Pearl Harbor and a love triangle. 

Does it appear in the movie (i.e. other than the end credits)? End credits. 
Is it important to the plot? No. 
Is it pleasing to the ear? A.

"Vanilla Sky" from Vanilla Sky sung by Paul McCartney

Movie Synopsis: A successful publisher finds his life taking a turn for the surreal after a car accident with a jaded lover. 

Does it appear in the movie (i.e. other than the end credits)? N/A.
Is it important to the plot? N/A. 
Is it pleasing to the ear? C-.

So what won?

"If I Didn't Have You" from Monsters, Inc.

 What would I have voted for? 

"May It Be" from Lord of the Rings: The Fellowship of the Ring

One of the most beautiful songs ever written. 

Analysis

Well, for the very last year in this BOS series, I have to say that LOTR was robbed. "May It Be" is way better than "Into the West" and it's a shame that song gets the glory. Also, woo-hoo, congratu-fucking-lations, Randy Newman, you finally got an Oscar for writing the same song over and over.

That does it, ladies and gentlemen. I attempted to listen to every BOS nominee. At this point in time, it's the best I can do. Soon, I'll write some sort of conclusion. Check back soon!