I hesitate to include this song because it's only nine years old. Yet, with a star like Timberlake, nine years seems like an eternity, especially considering how much his career has changed recently. So here it goes.
Back when this song came out, it wasn’t clear whether Timberlake could establish himself outside ‘N Sync. “Like I Love You,” the first single from the hilariously, pretentiously titled Justified, owed much to Michael Jackson. It was far from star-making material.
And then this came out:
When it comes to turning scandal and controversy into albums sold, no one does it better than Justin Timberlake. “Cry Me A River” would be the first of many times he would do this, using a Britney Spears look-alike to play the video’s cheating girlfriend.
Watching the video now, the look-alike is a distraction from an otherwise brilliant video. No one expected Timberlake to play a jilted lover – the one who breaks into his girlfriend’s house, films himself making out with another girl in her bed, and has the video playback on her television when she’s all alone in her house. Timberlake goes from angry to detached to just plain creepy in the span of four minutes, leaving us with a convincing portrayal of revenge that’s left no one happy.
Timberlake hasn’t recorded a song since that’s matched the despair of “Cry Me A River” – but here’s to hoping we’ll see more of his serious side if and when he decides to record a third album.
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