Producer: Timbaland
Album: Justified

"Cry Me A River" is a spiteful, revenge-stricken song full of pain, regret, and bitterness that pushed Timberlake's career beyond what anyone expected of him—maybe even himself. For fans of 'N Sync and the fairytale romance of Britney Spears and JT, their breakup was inevitably one of the biggest pop culture spectacles of the '00s. It's impossible for it not to be. It's all they talked about in interviews, and was the first step in a long-winded decline of Spears' career and personal health.

The Grammy-winning track, which peaked at No. 3 on the charts, begins with rain falling and a Gregorian chant. If it doesn't give you goosebumps, you've never had your heart broken. The synth-beat starts and in comes Timberlake's opening lyric: "You were my sun, you were my Earth." You feel all of his pain as a listener, and he got it all out as an artist. He was entirely broken, and this was his farewell to a seemingly fine but secretly fading relationship. Timbaland's contributions are also spot-on: the production, the chants, and "the damage is done, so I guess I be leaving" chants.

It's the track that made people completely forget about 'N Sync and start asking what Timberlake wouldd do next. He was never as painfully heartbroken as he was on this track, but maybe that's why Timberlake's career has survived. After marrying Jessica Biel, he's channeled that love into every single track on The 20/20 Experience, showing that he honestly writes his tracks on his emotions, leaving him with a career of personal albums that allow his fans to get a glimpse into his soul.—Lauren Nostro