5. “Cry Me a River”
Fresh off of the messy breakup with Britney Spears, Timberlake released a new go-to breakup song for men and women alike. In the video, Justin snuck into a Britney-look-a-like’s house to record himself and a hot brunette doing the nasty all over her house, then left the tape running on every TV in the house. “Cry Me a River” was a chance for every scorned lover to vicariously live out their revenge fantasy through JT.