The Most Bitter Celebrity Breakups
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.