The 10 Best (and Worst) Best Song Oscar-Winners of All Time

From 'Over the Rainbow' to 'It's Hard Out There for a Pimp,' the Best Song category's cream of the crop – and bottom of the barrel

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Best: "It's Hard Out Here for a Pimp" ('Hustle & Flow,' 2005)

Sure, go ahead and goof on how Three 6 Mafia's triumph gifted us with the unlikely but true phrase "the Academy Award–winning composers of ‘Slob on My Knob.'" But "It's Hard Out Here for a Pimp" – co-written by DJ Paul, Juicy J, and Frayser Boy, and performed in the film by future Empire headliners Taraji P. Henson and Terrence Howard — is so much more than the novelty element. (Or Three 6's infectious excitement after winning.) This song enabled the single most uncompromisingly underground act ever to take the Oscar stage to win the film industry's top honor – bringing long-overdue recognition to Black hip-hop artists in general and the Dirty South in particular.

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