One of the most interesting aspects of "Cry Me a River" is the undeniable connection the song had to Justin Timberlake's highly publicized breakup with pop superstar Britney Spears.
When the song was released, all anyone could think was that it was clearly about Britney, who was rumored to have cheated on Justin with a choreographer. Funnily enough, no one ever made similar accusations when NSYNC released "Space Cowboy."
More than any other Justin Timberlake song, "Cry Me a River" has always seemed as if it came directly from Justin's life. Few songs are as autobiographical as people assume this one is: the narrator's not just telling a story. He's telling a very specific story.
And if the lyrics weren't clear enough, the cheating ex-girlfriend in the music video is basically a Britney lookalike. Just sayin'.