The Ballad(s) of Justin and Britney, Vol. 2: ‘Everytime’

Sydney Urbanek
18 min readMay 26, 2020

“I may have made it rain / Please forgive me”

On ABC’s “Primetime” in November, 2003

This essay is the second of a two-part series on the music videos that came out of the Justin Timberlake/Britney Spears breakup. It’ll make the most sense if you’ve read “The Ballad(s) of Justin and Britney, Vol. 1: ‘Cry Me a River’” first.

“I’m embarrassed, can we stop for a sec?” asks an emotional Britney Spears about halfway through her Primetime interview, where we last left off. It was November of 2003, and Diane Sawyer had just pressed the young star about how “rough” things had been lately, from her breakup with Justin Timberlake the previous year, to her aunt’s ongoing cancer battle, to her parents’ recent divorce. “You’ve had a year that would test a lot of people,” Sawyer says. Britney agrees that it’d been “a weird time,” and is ultimately upset enough by the question that she needs to take a break.

Britney’s Primetime interview was tasked with a lot. It was set to air the day after she released In the Zone (2003), her most provocative (and, dare I say, best) album yet. But “the most famous 21-year-old on the planet,” as she’s introduced in the episode, had a couple things to answer for if she wanted the rollout to proceed smoothly. The breakup, naturally, was one of them. Once Britney has finished drying her tears, Sawyer asks about Justin’s “Cry Me a River” video. The star tells her story of seeing it for the first time while “on vacation,” then offers her take, clearly choosing her words carefully:

I don’t want to judge him or anything like that ‘cause that’s the way he had to deal with what happened, and that’s fine, but I just… I know that if I was in a relationship and something happened, I couldn’t really go there. But it’s all good. Let’s talk about something else.

Her comment was not only gracious but clever from a PR perspective. Justin had punched down, and while Britney understood the impulse on an emotional level as well as a commercial one, she’d found the move undignified. (Speaking to Rolling Stone a few months earlier, she’d called it “a desperate attempt.” Later, in the privacy of her own home, she’d dub it “pussy-fied. But hey, whatever gets you in the game, right?”) By extension, Britney had suggested that any allusions to the breakup on In the Zone —…

Sydney Urbanek

Writer on mostly pop music x moving images. Often at