This essay is the first of a two-part series on the music videos that resulted from the Justney breakup. Vol. 2 will be on Britney's Everytime video.Y'all seem bored, so: for the first essay in a two-part series on the music videos that came out of the Justin Timberlake/Britney Spears breakup, I wrote about "Cry Me a River" https://t.co/7FtFpofflN
— Sydney Urbanek (@sydurbanek) March 19, 2020
It provides insights into how Justin's Cry Me a River video helped frame him as the scorned, heartbroken man with Britney as the not-so-innocent cheater.
Justin's debut single, Like I Love You, was released in August 2002 and peaked at #11 on the Billboard Hot 100.
Ahead of his album's release that November, Justin went on Barbara Walters and talked about his breakup with Britney, saying "I promised to her that I wouldn't say specifically why we broke up." In that interview, Barbara also presses Justin on whether the couple actually kept their virginity pledge, to which Justin said, "Sure," with a laugh. In addition, he "cried himself to sleep" after their split.
When the music video dropped on TRL later that month, Justin told Carson Daly that the video was about him, not Britney, and that he had little to do with director Francis Lawrence's creative concept.
Lawrence later said there was an “unspoken agreement” between himself and Justin: "'Because [Justin and Britney] were on the same label; that’s part of the reason I thought the label would never, ever go for it. It was all about implying certain things, there’s little elements and details that play throughout and tie it in.'"

Jive Records, Britney and Justin's label had the chance to intervene in the video's release ahead of time, but opted not to. Lawrence said, "'[The label] went through a moment where it was like, 'What are we gonna do? Are we hurting a relationship with somebody else here?' But then it all went away. I’m not positive of the timeline on that because I wasn’t really around, it was record-label politics.'"
A little retrospective on 2007-2008 for those with a fuzzy memory. In an interview with Oprah in September 2007, Justin tells Oprah, "I haven't spoken to [Britney] in years. I mean, there's no ill will. I have nothing but love for her."
Six months after the Oprah interview, Justin alluded to Britney when he was inducting Madonna into the Rock and Roll Hall of Fame, saying "The world has always been full of Madonna wannabes, and I might have even dated a couple." This was five weeks after Britney was put on a psychiatric hold at an LA hospital.
Justin brought up their sex life on an SNL skit the following year. He has knocked Britney's career moves as recently as 2018.
Source 1, 2
Really good essay
