Best Original Song - 1964

"Dear Heart" from Dear Heart sung by Chorus.

Movie Synopsis: A lonely, single woman falls in love with an engaged man.

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

"Hush...Hush, Sweet Charlotte" from Hush...Hush, Sweet Charlotte sung by Al Martin

Movie Synopsis: The arrival of a lost relative, engulfs terror upon an aging southern belle, forever plagued by a horrifying family secret.

Does it appear in the movie (i.e. other than the end credits)? Unsure. My guess is an opening credits song.
Is it important to the plot? N/A
Is it pleasing to the ear? B+.

"Chim Chim Cher-ee" from Mary Poppins sung by Dick van Dyke and Julie Andrews

Movie Synopsis: A magic nanny comes to work for a cold banker's unhappy family.

Does it appear in the movie (i.e. other than the end credits)? Yes.
Is it important to the plot? Well...Bert sings about his enjoyment as a chimney sweep. You decide.
Is it pleasing to the ear? A-.

"My Kind of Town" from Robin and the 7 Hoods sung by Frank Sinatra

Movie Synopsis: A musical version of Robin Hood set in prohibition era Chicago featuring the Rat Pack.

Does it appear in the movie (i.e. other than the end credits)? Since it's a musical, yeah.
Is it important to the plot? Sure?
Is it pleasing to the ear? C.

"Where Love Has Gone" from Where Love Has Gone sung by Jack Jones

Movie Synopsis: A divorced couple's teen-age daughter stands trial for stabbing her mother's latest lover.

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

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So what won?
"Chim Chim Cher-ee" from Mary Poppins

What would I have voted for?
"Chim Chim Cher-ee" from Mary Poppins.

It's the strongest and the most memorable.

Analysis
The most surprising thing about 1964 is that more songs from Mary Poppins weren't nominated. And out of all the songs, "Chim Chim Cher-ee" is the one chosen from the bunch of gold nuggets including "Supercalifragilisticexpialadocious" and "A Spoonful of Sugar". Maybe there was a rule forbidding multiple nominations in this category. Hmmm...The rest of the nominees are standard Henry Mancini/Andy Williams-esque fair. That over the top, melodramatic sound was so popular then. I hope the same happens for hip-hop in forty years. Oh snap!