"Cry Me a River" is surprisingly baroque for a pop song, even by modern pop standards. Justin Timberlake's producers, Timbaland and Scott Storch, layer the song with texture upon texture, making it more appropriate for headphones than a car with its windows down.
As far as kiss-offs go (and there are a few on this list), "Cry Me a River" is more hurt than scorn, which makes the song genuinely moving. (Britney really did break the poor boy's heart.) It's also funky and, with its human beatboxing and Gregorian chant samples, a little weird.
Justin Timberlake is the only male artist from the late-90s bubblegum renaissance who managed to successfully transition to a serious solo career. You have to give it to Justin; the guy is ambitious. It's no secret the JT wants very badly to be the next Michael Jackson. He may fall short of that goal, even Jackson had a hard time at being Michael Jackson, but he's made some really good music because he aims so high.
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Justin Timberlake - Cry Me A River (Official Music Video) - The most amazing bloopers are here