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20 Greatest Best Song Oscar Performances

From Springsteen to Southern hip-hop and hot-buttered soul, Oscars’ grandest, grooviest musical showstoppers

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A prepubescent King of Pop, singing a love song to a rat; a Southern rap trio, paying tribute to the trials and tribulations of being in “the game”; a Canadian chart-topping superstar crooning hard enough to shatter glass chandeliers; a Portland, Oregon indie troubadour gently singing his way through an acoustic ditty. Look back at the Best Song Oscars of the last four-plus decades, and you’ll find an oddball mix of pop, rock, R&B, hip-hop, old-school showtunes, old-fashioned showstoppers and a few unclassifiable gems. We’ve grabbed 20 of our favorite Academy Award broadcast performances and ranked them from good to jaw-droppingly great. You think it’s hard out there for a pimp? Try choosing between Adele, Bjork, Springsteen and “Everything Is Awesome” for your top slot.

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Robin Williams, ‘Blame Canada’ (1999)

Thanks to one of the most unlikely nominations in the history of the Academy Awards, South Park: Bigger, Longer & Uncut‘s foul-mouthed ode to our neighbors to the North would be performed live for a crowd of millions — the question was, what to do with the repeated uses of the word “fuck”? Luckily, a galloping chorus gasped whenever Robin Williams hit the curse word (with the comedian strategically turning and mouthing the phrase). He did yelp “and that bitch Ann Murray, too!” with glee, however, while surrounded by a dance line of scantily clad women dressed as mounties. When the song lost to Phil Collins’ “You’ll Be in My Heart,” Trey Parker and Matt Stone later parodied the singer in a South Park episode the following year (and an Oscar eventually gets stuck up Collins’ butt). JP

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Elliott Smith, ‘Miss Misery’ (1997)

Late singer-songwriter Elliott Smith was never much for the spotlight, and watching him croon in front of the entire world feels like shining a flashlight through a ghost. Performing the acoustic stunner that Gus Van Sant commissioned him to write for the closing credits of Good Will Hunting, Smith warbles through the verses with the same bittersweet resolve that his voice brings to the film’s touching final moments. His evident (though admirably well-contained) nerves highlight the song’s beautiful fragility, and the moment has come to serve as a wonderful remembrance of this tragic musician — not even the Oscars could prevent Smith from being himself. DE

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Bruce Springsteen, ‘Streets of Philadelphia’ (1994)

Nobody on Earth is more comfortable singing for large crowds than Bruce Springsteen, and he took to the Oscar stage with the same steely confidence that he's always brought to every other arena-sized venue on the planet. Still, The Boss was palpably vulnerable as he quivered behind the microphone on that March night in 1994, digging deep to deliver this soul-stirring elegy to the victims of the AIDS epidemic. Captured in a delicate close-up that slowly zooms tighter on Springsteen's face, the performance is made all the more powerful for how it seems to weigh down one of our most irrepressible showmen. DE

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