Song She Inspired: Justin Timberlake - "Cry Me a River" (2002)
Highest Position on the Billboard Hot 100: 3
In 2002, Justin Timberlake began his solo (post-N*SYNC) career with a bang: His album, Justified, would go multi-platinum, and its lead single, "Cry Me a River," would win the Grammy for Best Male Vocal Performance. But about that song and video—didn't it all seem a bit too get-back-at-Britney-ish for a mature artist? Timberlake might have sensed as much, and claimed in interviews that the song wasn't about her, and that the blonde in the video wasn't meant to look like her. He kept up this story for years, and approximately zero people believed him.
In 2011, producer Timbaland confirmed that the song had come about after Timberlake got off a brutal phone call with Spears.