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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Elton John and Backstreet Boys, "Philadelphia Freedom" (2000)

Not quite the mash-up that arose from similarly incongruous pairings, the Backstreet Boys' cameo on "Philadelphia Freedom" essentially consisted of them crowding around Elton John's piano and offering backing vocals and supportive hand gestures. Elton, however, was appreciative of the "I Want It That Way" hitmakers: "I've slept with all the boy bands. I know them all," he quipped backstage after taking time to praise the vocal prowess of A.J., Howie, Nick, Brian and Kevin.

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