Best Original Song - 1959

"The Best of Everything" from The Best of Everything sung by Johnny Mathis

Movie Synopsis: An expose of the lives and loves of Madison Avenue working girls and their higher ups.

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? B+.

"The Five Pennies" from The Five Pennies sung by Eileen Wilson

Movie Synopsis: A cornet-player quits the music business to care for his sick daughter who later encourages him to reform his band.

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.

"High Hopes" from A Hole in the Head sung by Frank Sinatra

Movie Synopsis: An impractical widower tries to hang onto his Miami hotel and his 12-year-old son.

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

Is it important to the plot? Father son bonding.

Is it pleasing to the ear? B. 

"The Hanging Tree" from The Hanging Tree sung by Marty Robbins 


Movie Synopsis: A doctor saves a local criminal from a mob  trying to hang him, but then tries to control the life of the young man, realizing that he can exploit his secret

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

Is it important to the plot? N/A.

Is it pleasing to the ear? B+.

"Strange Are the Ways of Love" from The Young Land sung by Randy Sparks

Movie Synopsis: An American gunslinger kills a Mexican man in California immediately after the Mexican-American war.

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-.

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So what won?
"High Hopes" from A Hole in the Head

What would I have voted for?
"The Hanging Tree" from The Hanging Tree

Definitely the most interesting and the ending film clip helped immensely.

Analysis
Oh the 50's...this was a pretty weak year, I must admit. No definite screaming winners. "High Hopes" is, of course, the most popular and recognizable (and irritatingly charming). So, it deserves its Oscar. Too bad all the songs from Sleeping Beauty are based on previously published music.