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It's so strange. Between the start of the video, the teasers and the actual meat of the video, they've shown such self-awareness, but an unusual final direction. He and whoever they worked with for this clearly know all about the iconic imagery Justin is sort of compared to or could strive to replicate and they throw it in our faces. But to feed that to the public and fans and then settle on a "gotcha" video that stays in the lax NSYNC days is a strange decision.
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As a continuation of this comment, maybe that's what they were shooting for. He's talked a lot in the past about how his greatest idol is Michael Jackson, and he's clearly addressed the work of MJ, Elvis and most recently, the look of James Dean. The first bit of the video sort of feels like a tease of what he wants to do, what he looks up to in pop, the type of iconic character he wishes to be for today's world. But it sort of rears back to reality and what he's trying to do right now, which is transitioning from child star to adult pop singer. He knows there's only one man that's made that transition successfully this millennium because that man is one of the two people that tried to sign him in the beginning.