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1. Kanye West: "George Bush Doesn't Care About Black People"
Honorable Mention: Kanye West interrupts Taylor Swift at the VMAs
But the more uncomfortable moment has got to be Kanye's off-teleprompter rant during the Concert for Hurricane Relief in 2006. Just watch Mike Myers look at him in utter terror and disbelief, knowing that they’re on live TV and that he's stuck there with him. And when it all culminates with "George Bush doesn't care about black people," it was clear: Hurricane Kanye had come to town.
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