18. Justin Timberlake – “Cry Me A River” – Justified
Breakups suck, but if you can sing and/or write songs, you can flips it into a pretty nice career for yourself. JT’s “Cry Me A River” at the time was his biggest song ever and it all drew from his much-publicized breakup with pop star Britney Spears…we think. C’mon b, you all saw the video.
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