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'.
Justin Timberlake became much more than just a pop heartthrob, but when he released "Cry Me a River" in 2002, he was frankly, just a pop heartthrob.
His calling card? Being that cute guy who can dance. Or as one music journalist put it, "he is adored by millions of fans, many of whom have been adolescent girls" (source).
As embarrassing as it may be to admit, at the onset, there wasn't much more to Timberlake's fame than that. He was the Justin Bieber of the late 1990s and early 2000s: good-looking, young, high-voiced, and charming. He was a member of the Mickey Mouse Club alongside Britney Spears, Ryan Gosling, and Christina Aguilera. And in his mid-teens, he gained international fame as the primary hot guy in the five-person teen pop get-up NSYNC.
All of that was nice and all, but "Cry Me a River" was the pivotal moment in his shift from teen boy-band star to solo act. It might seem silly, but with Justified, Timberlake solidified the fact that he really did have a talent for singing, dancing, and charming his audiences.
"Like I Love You," the first single off the album, was still pretty much a shallow dance tune, even if was a bit spicier than his NSYNC stuff. With the release of "Cry Me a River," though, the world began to consider Timberlake as a serious artist.
Shortly after, he also got on a lot of people's good side by beginning a public routine of self-mockery on late-night shows like Saturday Night Live. So, as Timberlake did some growing up, he also demonstrated some chops as an actor and as a funny guy.
In other words, pretty face he is, but he's more than just that.