Britney Spears and Justin Timberlake, 2002
A pop star relationship gone wrong is only as good as its breakup song. And Justin Timberlake's "Cry Me a River" was goood: "You don't have to say what you did. I already know. I found out from him." When the former Mouseketeers turned pop megastars ended their love story in 2002, rumors of Britney Spears' alleged cheating surfaced. And while Spears never admitted to infidelity, she didn't have to. The video for Timberlake's hit single "Cry Me a River" features a Spears doppelgänger leaving her home with another man while Timberlake looks on. He then breaks into her home, tosses a photo that contains people who look remarkably like the two of them, films himself kissing another woman and leaves it playing on a television in her home. Though Spears called the music video a "desperate attempt" in her October 2003 Rolling Stone interview, Timberlake ultimately got the last laugh by dating Hollywood stars Cameron Diaz and Jessica Biel while Spears married Kevin "K-Fed" Federline and spiraled out of control.