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'It’s Hard Out Here For A Pimp' from 'Hustle & Flow' (2005)
Why it didn't deserve the win: In some ways, it feels grinchy to complain about a rap tune winning best original song since only two have: “Pimp” and “Lose Yourself” from “8 Mile,” and its victory certainly marked a switch from the ballad-du-jour, typical Oscar fodder. But in a year when “It’s Hard Out There For a Pimp” was probably the worst song of the three contenders, it’s unavoidable.
Better choice: “Travelin’ Thru” (“Transamerica”)