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Tough call, but I think the tie goes to Jackson. For anyone younger readers, it's hard to overestimate just how much of an "event" even his video releases were. I mean, who else from then could do a world premiere in prime time? Who could pull it off today?

Another point in MJ's favor is that a Prince song could be covered/performed by any number of different artists (see the Goo Goo Dolls cover of "I Could Never take the Place..." as Exhibit A)- that speaks to his brilliance as a writer and being attuned to what makes a pop song great.

But an MJ song was an MJ song. Period. No one's covering "Thriller."

As for the next pairing, I'm going to have to think about that one!

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