20 Weird and Wild Grammy Collaborations

Paul McCartney singing with Linkin Park and 19 more mash-ups from music's biggest night

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Alicia Keys and Frank Sinatra, "Learnin' the Blues" (2008)

A consummate professional, Frank Sinatra wasn't going to let a little thing like being dead for ten years keep him from opening the Grammys' 50th Anniversary show. After a clip (from the 1963 show) of Ol' Blue Eyes explaining how you win a Grammy (it's "not for selling a million records mind you — you get bread for that — this is for contributions to the art of recording"), Alicia Keys took the stage to play piano, dueting with a video image of the Chairman, though her ad libs ("Sing it, Frank") showed her trying a little too hard to generate chemistry.

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