Pop necessitates a mastery over a variety of styles. You don't need to do everything, but you do need to be flexible; a master of arms as it were.
Both McCartney & Jackson nailed their style of music, but they tend not to branch out further. When I think of the folks making pop music today: Pink, Katy Perry, Justin Timberlake, Lady Gaga, and to a lesser extent Bruno Mars & Ke$ha I think of people all over the freakin map.
I think its why pop bands never fair as well. Studio musicians are almost a must. The legends certainly pushed an envelope, but the way technology is advancing, they never stood a chance. And in Pop music, there never should be a classic, really.
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