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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Keely Smith and Kid Rock, "That Ol' Black Magic" (2008)

Pop vocalist Keely Smith performed at the very first Grammy Awards show, back when it aired as part of the NBC Sunday Showcase in 1959. That year, she and Louis Prima won the inaugural Grammy for Best Performance by a Vocal Group or Chorus for their recording of "That Old Black Magic." To celebrate the 50th anniversary of the awards in 2008, Smith returned, then a spry and lively 75 years old, but Prima couldn't make it, on account of being dead for 30 years. Of the many non-Louis-Prima living male singers available (David Lee Roth would've killed it), somebody decided on Kid Rock, who occasionally sounds like he knows what he's doing. Also, that's Dave Koz hamming around beside them on saxophone.

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