The Most Bitter Celebrity Breakups

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Justin Timberlake and Britney Spears

JT and Britney Spears were the ultimate “it” couple back when they dated from 1999-2002. but a young Timberlake was devastated when he found out that Spears was creeping behind his back. He used his heartbreak to provide us with “Cry Me A River.” The music video even included a Spears look-alike, and the song helped launch Timberlake as a successful solo artist.

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