“Cry Me A River” by Justin Timberlake (2002)
Even if Justin Timberlake disputes the claims, “Cry Me A River” was clearly targeted at Britney Spears following their extremely public breakup in 2002. In the video, Timberlake stalks a (notably Britney-esque) blonde woman, breaks into her house, and films himself sleeping with another woman. He leaves the recording for his ex-girlfriend to find. The premise is gross and creepy, but at the very least, it’s Timerblake’s most memorable video to date.
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