The Ballad(s) of Justin and Britney, Vol. 2: ‘Everytime’
By: Sydney Urbanek
Tags: Music, Britney Spears, Justin Timberlake, Madonna, Music Video

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. It was edited by Jasmine Mani.

“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 — and Sawyer can’t quite get her to admit to any during the interview — were respectful of Justin’s humanity. Britney had just drawn a clear line between his approach (read: ungentlemanly, perhaps cruel) and what she considered her own to be, though it was still too early to know what that was.

On the cover of “Esquire” in November, 2003

She also tells Sawyer that she was hurt by Justin talking about their sex life on HOT-97 FM. “I just felt very exploited and very… weird,” she says. Audio of him being asked whether he “fuck[ed] Britney Spears” and answering in the affirmative, however, is somehow spun into a question from Sawyer about the example that Britney is setting for her little sister, Jamie Lynn. There’s a slut-shamey overtone to many of Sawyer’s lines of questioning, which is telling of how the press was already treating Britney in 2003—even while in conversation with Britney herself. “What happened to your clothes?” Sawyer asks early in the interview of the star’s recent attire, frankly sounding more like a concerned aunt than a journalist. She then cycles through a series of laminated photographs of Britney from recent shoots, at one point goading her into admitting that she regrets that month’s Esquire spread. (It’s unclear watching the interview whether she really does or merely feels like it’s probably a good idea to say so in the moment.)

“I think it’s an okay thing to… express yourself,” Britney declares at one point, explaining that she doesn’t set out to please everyone. Her word choice here was interesting given her developing friend/mentor-ship with Madonna. Alongside Janet Jackson and Whitney Houston, Madonna has always been a role model of Britney’s. (In Steven Daly’s famous Rolling Stone cover story of Britney from 1999, he notes that her brother remembers her “dancing in front of the TV, trilling Madonna’s ‘Like a Prayer’” as a kid. Britney, who’s 17 in the story, is also said to already “[fancy] the Madonna model” of fame, in terms of versatility and business sense.) Madonna is the only celebrity that Sawyer focuses on as much as she does Justin. The pop provocateur had recently lectured Britney about her smoking habit, so Britney was trying to cut back. At some point over the next several months, Madonna would introduce Britney to Kabbalah, which the latter would study until 2006. And, of course, there was the 2003 MTV Video Music Awards (VMAs) broadcast back in August. Britney and Christina Aguilera had teamed up for a duet of “Like a Virgin,” writhing around on the floor in wedding dresses like Madonna had done at the first ever broadcast in 1984. Madonna then popped out of a cake dressed as a groom to sing her latest single, “Hollywood,” pausing in the middle to open-mouth kiss both former Mouseketeers.

At the 2003 MTV VMAs on August 28, 2003

Justin, yet another Mouseketeer in attendance, was nominated for seven VMAs that night — he ended up going home with three, two for the “Cry Me a River” video — and his presence at Radio City Music Hall in that moment was a godsend for the show’s producers. Getting his reaction to the Madonna/Britney kiss was enough of a ratings priority that the Madonna/Christina one ended up happening largely off-screen. (As a result, the latter kiss is relatively less remembered. “I definitely saw the newspaper the next day and it was like, ‘Oh, well, I guess I got left out of that one,’” Christina said in 2018.) Justin told one interviewer that night that he’d found the kiss(es) “sexy,” but changed his tune a couple weeks later when he said on The Sharon Osbourne Show that he wasn’t “upset about the kiss, [he] just wasn’t impressed.” (It’s hard to picture him saying something even remotely disparaging about Madonna as of 2007, the year she invited him, Timbaland, and the Neptunes to co-produce, co-write, and be featured on Hard Candy [2008]. As a reminder from last time, Justin would ultimately be chosen to induct her into the Rock and Roll Hall of Fame.)

But to come back to Madonna and Britney’s relationship, the former imbued the kiss with an almost spiritual significance: “I am the mommy pop star and she is the baby pop star. And I am kissing her to pass my energy on to her.” The two had decided during VMAs rehearsals that they wanted to work together in a more formal capacity. The resulting track, “Me Against the Music,” became In the Zone’s lead single in October, with a Paul Hunter-directed video whose every frame seemed engineered to induce gay awakenings. In her recent Rolling Stone interview about the album, Britney had said, “I think this record is where I’m at right now in my life. It’s sensual, it’s sexual.” Teaming up with Madonna wasn’t a bad way to usher in a more provocative era. Britney could explain away some of her antics by saying that they were Madonna’s idea, as she did after the kiss. It also positioned her as a potential successor of sorts. (Variations of this strategy have worked since: Christina kicked off her Bionic era in 2010 with “Not Myself Tonight,” a video that’s more or less a Madonna tribute. Beyoncé, too, invoked Madonna when she released her self-titled visual album in 2013, naming her as a main source of inspiration and nodding to multiple Madonna videos in her own.) It’s safe to say that the In the Zone era had been launched with a bang. So now what?