What's Been the Biggest Oscar Shocker of All Time?4 of 11
The rap group Three 6 Mafia is among the most unlikely Oscar winners of all time. At the 2006 Oscars, their song "It's Hard Out Here for a Pimp" from the hip-hop drama Hustle & Flow beat the heavily-favored Dolly Parton song "Travelin' Thru" from Transamerica. Host Jon Stewart quipped, "For those of you who are keeping score at home, I just want to make something very clear: Martin Scorsese, zero Oscars; Three 6 Mafia, one." (Scorsese won an Oscar a year later.)
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