Best Original Song - 1965

"The Ballad of Cat Ballou" from Cat Ballou sung by Nat King Cole and Stubby Kaye 


Movie Synopsis: A woman seeking revenge for her murdered father hires a famous gunman, but he's very different from what she expects. 


Does it appear in the movie (i.e. other than the end credits)? Yes, and then some credits.
Is it important to the plot? It introduces Cat Ballou.
Is it pleasing to the ear? C-.


"The Sweetheart Tree" from The Great Race sung by Jackie Ward 


Movie Synopsis: Comedy about an early 20th century car race across three continents. 


Does it appear in the movie (i.e. other than the end credits)? I don't know...I think so. 
Is it important to the plot? To the love story. 
Is it pleasing to the ear? B+.

"The Shadow of Your Smile" from The Sandpiper sung by Jack Sheldon 


Movie Synopsis: A free-spirited, young, unwed mother seduces a Episcopalian priest. 


Does it appear in the movie (i.e. other than the end credits)? I don't know. 
Is it important to the plot? Ditto.
Is it pleasing to the ear? C.

"I Will Wait For You" from The Umbrellas of Cherboug sung by Catherine Deneuve and Nino Castelnuovo 


Movie Synopsis: Two young lovers are separated by war. 


Does it appear in the movie (i.e. other than the end credits)? Yes. 
Is it important to the plot? Yes...it's the lovers vow to one another.
Is it pleasing to the ear? A.

"What's New Pussycat?" from What's New Pussycat? sung by Tom Jones 


Movie Synopsis: A playboy who refuses to give up his hedonistic lifestyle to settle down and marry his true love seeks help from a demented psychoanalyst who is having romantic problems of his own. 


Does it appear in the movie (i.e. other than the end credits)? I don't know.
Is it important to the plot? Establishing mood?
Is it pleasing to the ear? C+. 


So what won?
"The Shadow of Your Smile" from The Sandpiper

What would I have voted for? 
"I Will Wait For You" from The Umbrellas of Cherbourg 

I, like so many, was introduced to this song through an episode of Futurama. (The one with Fry's dog. Yeah, you know the one). This is just a beautiful song and integral to the plot. The two vow to wait for one another, and then both go back on the promise. It sort of makes the song a lie, making it all the more heartbreaking. 


Analysis
Going into the 60's, we can see a shift to more "popular" music, at least with "What's New Pussycat?" I'm also pretty sure "The Shadow of Your Smile" had some radio success. On a personal note, I'm glad I found the cheesy "The Sweetheart Tree".