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Ah, those were the days. When Britney and Justin were young and innocent, fresh out of the Mickey Mouse Club.
The pair met when they were barely teens, and dated from 1999 until early 2002, when they abruptly broke up. Although both have been extremely reticent to share details with the media, the rumor that Spears cheated on Justin with a choreographer circulated hotly around that time.
"Cry Me a River," which was released in late 2002 as the second single off of Timberlake's debut solo album, was the perfect pop fuel for the fiery rumors of their heated breakup.
Of course, "Cry Me a River" was a song Timberlake co-wrote with others, and it may or may not have been about Spears at all.
It's a bizarre perception regarding celebrity that makes us think pop singers need to be literal and personal in their repertoire. Realtalk: pretty much every pop singer has done a few songs that weren't about their own lives.
On the other hand, JT did take it to another place with the "Cry Me a River" music video, released in 2003. The woman who plays the filthy rich cheating ex in the video looks strikingly similar to Spears, and she never completely shows her face from behind her newsboy cap and sunglasses.
In step with their usual approach to gossip, both Britney and Justin denied that the video contained any personal content, and absolutely everyone in the world believed them both, because celebrities don’t lie.
"The video is not about her. The video is about me," Timberlake told the press. (Source)
Then he dressed up as an omelet and made everyone love him. Well, if that's all it takes.
Let's be real. There's no way Justin Timberlake and his media-savvy handlers could have overlooked the possibility that "Cry Me a River" might be interpreted as a stab at Britney. The man might be cute, but he's not stupid. Plus, in 2002, Spears still had a pretty good reputation and was considerably more famous than JT.
She was, for example, the #1 image-searched woman of 2002, according to Google. Good looks or not, Timberlake didn’t even make the top 10, getting beat out by dudes ranging from Brad Pitt to Marilyn Manson.
So, lo and behold, Timberlake finally revealed his inspiration for the song 10 years after its release. And of course it was Britney. Come on, Justin.
It's probably wise to just accept that "Cry Me a River" is part-lament, part-publicity-stunt, all good pop music, and call it a day. Point for Timberlake.