Justin and Britney were the quintessential pop couple of the late 1990s and early 2000s, but young love rarely ever lasts and the duo called off their relationship in 2002. Timberlake quickly released "Cry Me a River," a scorned anthem which is reportedly about his failed relationship with Spears as a result of an affair. In the video, Timberlake even included a Britney-lookalike who cheats on him to hit the point home. Burn. —XFINITY Entertainment Staff (Photo by Frank Micelotta/Getty Images)
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