Best Original Song - 2005

"In the Deep" from Crash sung by Kathleen York 

Movie Synopsis: Several stories interweave during two days in Los Angeles involving a collection of inter-related characters. 

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

"It's Hard Out Here for a Pimp" from Hustle & Flow sung by Terrence Howard and Taraji P. Henson 

Movie Synopsis: With help from his friends, a Memphis pimp in a mid-life crisis attempts to become a successful hip-hop emcee. 

Does it appear in the movie (i.e. other than the end credits)? Yes. 
Is it important to the plot? Actually, yes. It's his lead single or something... 
Is it pleasing to the ear? B. (In a laughing way).

"Travelin' Thru" from Transamerica sung by Dolly Parton 

Movie Synopsis: A pre-operative male-to-female transsexual takes an unexpected journey when she learns that she fathered a son, now a teenage runaway hustling on the streets of New York. 

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

So what won?
"It's Hard Out Here For a Pimp" from Hustle & Flow

 What would I have voted for? 

"It's Hard Out Here For a Pimp" from Hustle & Flow

Yes, I'm just as shocked as you. I can't believe every time a rap song has been nominated, I've voted for it. 

Analysis

For the first time since 1988, only three songs are up for the Best Original Song Oscar. It was indeed a very weak year. But the right song won. When the song is integral to the plot, it's really hard to fight. Also, it's damn catchy and entertaining.