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 — 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?

“Toxic” (2004)

“Toxic” seems like it would’ve been the obvious pick for the album’s next single, but Britney had actually been trying to choose between two other songs from In the Zone: “Outrageous,” which eventually became its fourth single, and “(I Got That) Boom Boom.” She eventually went for “Toxic” because it sounded “really different.” The single and its video, the most expensive one she’d ever made at that point, were both released on January 13. In December, Britney had sent director Joseph Kahn a rough concept for a video about “a slinky female agent out for revenge against an ex-lover.” Kahn cast a few of his friends, and they shot it in Los Angeles shortly thereafter.

“Toxic” (2004) cont’d

The “Toxic” video, which ends with Britney poisoning her former flame (Martin Henderson), wasn’t necessarily about Justin, but perhaps it wasn’t not about Justin. While Britney’s character is securing her green vial of poison, there are three shots — so quick that it was a feat to grab screenshots of them, almost as if they weren’t meant to stick out — that show Henderson’s character in the shower with a woman. (When Britney arrives to kill him, this other woman’s silhouette is still visible in the shower.) The shower setting may have been coincidental, but it’s also possible that Britney was winking at the public in reference to “Cry Me a River,” especially since she’s had a reputation since her “…Baby One More Time” days for knowing exactly what she wants her videos to look like, “down to the smallest detail.” Perhaps she was also implying something in having her ex-lover be in there with another woman, but only Britney really knows. (Some of her fans have speculated that Justin wasn’t entirely faithful to her during their relationship, and was simply the only half of the couple to take the other half’s infidelity public.)

Critically and commercially, “Toxic” was an immediate smash. (It would eventually land Britney her first and only Grammy.) For a solid month, it received plenty of daytime airplay on MTV — that is, until Justin ripped Janet Jackson’s costume during the Super Bowl halftime show in February, exposing her breast to 140 million people. Chaos ensued in the television world, and MTV was no exception; the network had actually produced the halftime show. “Given the particular sensitivity in the culture right now, we’re erring on the side of caution for the immediate future,” said a spokesperson. Six “racy” videos, including “Toxic,” were indefinitely moved to late-night programming. I’m obviously not suggesting that this was Justin’s plan all along, but it’s actually rather impressive that he managed to deal Britney yet another blow from so far away. I’ll come back to the Super Bowl later.

Annet Artani and Britney

In March, Britney began her Onyx Hotel Tour (which she’d ultimately have to end two and a half months early due to a knee injury). It was also time to prepare In the Zone’s next single, “Everytime,” for which she’d be shooting a video in the middle of the month. The song was described by MTV as “a plea for forgiveness for inadvertently hurting a former lover.” When she’s asked by Diane Sawyer on Primetime who’d inspired the ballad’s lyrics, Britney says that she wants to “let the song speak for itself.” However, Annet Artani—a friend and backup vocalist to Britney at the time, not to mention the song’s co-writer—has said that it was very much inspired by Justin: “We commiserated because she, at that time, had broken up with Justin. I was just breaking up with this guy, so we kind of like — I think we kind of needed each other.” Britney and Artani spent a brief stint living and writing songs together — first in Los Angeles, then in Lake Como. The latter location is presumably where Britney was “on vacation” when she saw the “Cry Me a River” video. It and Justin’s recent radio behaviour were reportedly the two main catalysts for “Everytime.” “He was really exposing some stuff that [Britney] probably didn’t want out there, and in front of her little sister,” Artani explained. “I remember her sister being mortified and her being mortified. I’m sure that really hurt her.” “Everytime” was one of the first songs finished for In the Zone.

Britney has said that she “wrote the whole [song] from scratch on the piano. Musically there was no track or anything. I was just at my house and I did the whole thing by myself. […] It’s one of the songs that when you hear, it’s like the kind of song when you go to heaven. It kind of takes you away.”

“Everytime” (2004)

It was decided that the “Everytime” video would be directed by David LaChapelle, who’d shot Britney’s iconic Rolling Stone cover in 1999. With Leaving Las Vegas (1995) as its main stylistic reference point, the plan was to have Britney take a handful of prescription pills and drown in her bathtub. She’d reportedly wanted “to respond to rumors and reports that she’s teetering on the brink, seeking help, in therapy or otherwise disturbed.” MTV obtained and reported on this early treatment on March 9, understandably interpreting the death described as a suicide. Many people wrote in expressing their concern. “Suicide occurs at an alarming rate, and this video seems to glorify it,” read one letter. “I have lost a friend to suicide, and the concept of this video disgusts me.” On March 12, Britney’s team released a statement explaining that the concept would be adjusted “due to the potential for a fictional accidental occurrence to be misinterpreted as a suicide.” The tweaked treatment was filmed over the ensuing 48 hours.

“Everytime” ultimately premiered on April 12 on MTV’s Total Request Live (TRL). “It’s more like a movie,” Britney explained when she called in. “It’s different than anything I’ve ever done before. It’s dark and it shows me in a different light. Of course, I’m going to go back and do dance videos, but I wanted to be inspired and challenged.”

The video’s opening shots establish that we’re with Britney in Las Vegas (though it was filmed in Los Angeles). She and her partner (Stephen Dorff) pull up to a back entrance to their hotel in a white limo, visibly tense. He’s on the phone and doesn’t seem to want to talk to her; there’s an empty Jack Daniels bottle on the floor that tells a story in itself. A horde of crazed fans and paparazzi are waiting for them at the entrance. Britney armours herself with a pair of sunglasses and a Birmingham Barons cap before getting out of the vehicle. Security guards do their best to protect her and Dorff’s character as they make their way into the building, but they’re swarmed. Britney’s hit in the head with one photographer’s camera; she cries out in pain, but we don’t hear it. Once inside, Dorff spots a shelf of tabloids with Britney’s face on them, and angrily throws an armful at a second photographer. The couple fights as security escorts them through the service corridors of the hotel. One of the video’s takeaways is already clear: fame comes with its challenges, but being famous and in love is a whole other ordeal.

“Drowned World / Substitute For Love” (1998) / “Everytime” (2004)

Already, there’s a considerable amount of overlap with Madonna’s video for “Drowned World / Substitute For Love” from 1998, directed by Walter Stern. Madonna, like Britney, is chased by fans and the press as she makes her way around London. “Found myself in crowded rooms, feeling so alone,” she sings. Stern’s video was controversial because it came out less than a year after the death of Diana, Princess of Wales, and involves Madonna being chased by photographers on motorcycles. The star briefly finds solace in the service corridors of a hotel, just as Britney does in “Everytime.” She and a housekeeper exchange kind smiles — until the latter pulls out a disposable camera and takes a snapshot. The video implies that nowhere is really safe from unwanted gazes when you’re a celebrity. (“Cry Me a River” arguably does the same, instead maliciously wielding this fact at another celebrity.)

“Drowned World / Substitute For Love” and “Everytime” ask viewers—implicitly in Madonna’s case, and explicitly in Britney’s—to imagine worst-case scenarios for their respective stars as a result of our obsession with them.

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

When Britney and Dorff’s character finally reach their hotel room, she’s furious with him, seemingly for his lashing out at the one photographer. “You always do this!” she yells. He apologizes, but when she doesn’t accept it, he throws a vase of flowers at the wall. He plops down on the couch while she heads for the bathtub; both smash something out of anger. Britney pulls her outfit up over her head to reveal her fairy tattoo, the one that Justin may have nodded to in the “Cry Me a River” video. Only once she’s in the bath does she realize that she has a head wound from where she was hit with the camera — not to be confused with the red Kabbalah bracelet on her wrist, which arguably looks like a wound at first glance (and is sometimes misinterpreted as such, including by my eight-year-old self). It’s at this point that Britney gets to the bridge, or what are arguably the four most important lines of the song.

I may have made it rain
Please forgive me
My weakness caused you pain
And this song’s my sorry

The bridge is at once an admission of fault—though it’s obviously still not our place to decide what exactly she did—and a potential reference to the “Cry Me a River” video; it conjures up that image of a hooded Justin outside Britney’s house as it pours. She then loses consciousness in the bathtub.

Oh baby, baby

In a separate timeline, Britney sings to us from inside a hospital, where she watches as doctors try and fail to revive her. Her performance of the song directly to the camera implicates viewers in the scenario somehow; it’s our insatiability—our tabloids bought, our gossip sites clicked on—with her off-duty self that has allowed this to happen. In the next room over, a baby is born, and Britney continues to sing to us, as if to suggest that she’s been reincarnated as this newborn. Reincarnation was one of the themes that she’d specifically wanted to address with the video (not to mention a Kabbalist belief). She’d forgotten to mention that when she called in to TRL, so she called back while the video was airing and asked host Carson Daly to explain this. As Alessa Dominguez has written of “Everytime,” it’s “as if on some level Spears understood that growing up in the Britney brand might be an impossible project, and the only narrative possibility was death and reborn innocence.”

In the end, Britney is killed by a paparazzo’s camera — a metaphor that, while perhaps a tad heavy-handed, inched dangerously close to becoming a prophetic one over the next several years of her life. In the “Everytime” video’s most haunting shot, a man clamours for an autograph from Britney as she’s carried into the ambulance on a stretcher. (It’s vaguely reminiscent of Lady Gaga’s “Paparazzi” video from 2009, where, after being thrown from her balcony by her boyfriend, photographers arrive to take photos and compliment her on her appearance as she lies there in her own blood.)

“Everytime” (2004) cont’d

Rather than retaliate at Justin—I couldn’t really go there—Britney had simply made a series of pleas. With the song itself, she asked for some forgiveness from the man she’d wronged; with LaChapelle’s video, she asked for privacy. Rather than lingering on the alleged infidelity/ies, the video seemed interested in starting a new conversation altogether. It was a reminder that Britney was mortal—something the public badly needed to hear, even if it historically hasn’t been great at listening.

The video seems set to end with one final shot of the newborn—until we’re suddenly back with Britney in the bathtub, a Britney who’s very much alive. She smiles and laughs knowingly in a way that harkens back to the ending of the “…Baby One More Time” video, the one that confirms that everything we just saw happened inside her head. There are different ways to read this, but one of them is that we’ve just been massively fucked with. Britney serves up a sobering depiction of her own demise so that we’re left wondering how we may have prevented it, then lets us know that we still can.

“…Baby One More Time” (1999) / “Everytime” (2004)

Around the same time that she released the “Everytime” video, Britney met dancer Kevin Federline, who’d actually backed Justin in “Like I Love You.” In June, while shooting the video for “Outrageous,” she suffered the knee injury that doomed the remainder of the Onyx Hotel Tour. Britney and Federline announced their engagement later that month, and they were married in September. In November of 2006, shortly after the birth of their second son, Britney filed for divorce. By February, she was engaged in a custody war over her children, her aunt had finally lost her battle with ovarian cancer, and Britney was in and out of rehab. “The media’s obsession with her went into overdrive when the ultimate ‘overexposed blonde’ rebelled against all the contradictory fantasies projected onto her,” wrote Dominguez:

…shaving off her blond sex symbol tresses and angrily pointing her umbrella at paparazzi in February 2007. […] That Spears’ polished pop star image was unraveling — seemingly outside of her control — only made her more relevant than ever.

On the L.A. stop of Madonna’s Sticky & Sweet Tour on November 6, 2008

Much, much later, in November of 2008, Madonna had both Justin and Britney make surprise appearances at the Los Angeles stop of her Sticky & Sweet Tour. Britney came out for “Human Nature,” Madonna’s fuck-the-press anthem from Bedtime Stories (1994), and Justin joined Madonna for one of their Hard Candy collaborations, “4 Minutes.” (Britney and Justin don’t seem to have interacted that night.)

Justin had spent 2008 thus far collaborating with some of the biggest names in music and continuing to make a name for himself in the acting world. He’d also won a couple Grammys, including one for “What Goes Around… Comes Around.” That video features a cheating blonde (Scarlett Johansson) who at one point pretends to drown for Justin’s attention. Whether he’d intended for this to come off as a dig at “Everytime” is unclear. Britney, for her part, was about to release Circus (2008), her second post-breakdown album. While Circus would debut in the number-one spot on the Billboard 200, her image had yet to fully recover from the previous year’s events. As she says in Britney: For the Record (2008), a documentary that premiered on MTV a week after the album’s release, “I’m having to pay for it for a really long time.” Madonna was interviewed for the film before the Sticky & Sweet show, telling the camera, “I think ‘What was I thinking?’”—a line from “Human Nature”—“is the first question a person who starts to examine themselves asks themselves.” “I’m definitely angry with myself for letting people take advantage of me,” Britney says in the next scene:

…angry with people for taking advantage of me, and for letting them go on for so long. But I have to go on with it. I look at it for what it is and I have to move on with it, let it go.

But even though more than a decade has passed since, 2007 still constantly seeps into how Britney is spoken and written about, in part because she still remains under the conservatorship that was first imposed in February of 2008. As Roslyn Talusan has noted, “It’s as if the public’s perception of Spears is frozen in time, where we’re unable to see past her breakdown to fully recognize her as a human being.”

At one point in For the Record, Britney rightly remarks that Justin “was part of the magnitude that I’d become,” fame-wise. The man is an immensely talented musician and performer, someone who’s responsible for a lot of music that I hold dear (and have written highly of). It’s equally true that he harnessed his adjacency to Britney rather cruelly when it was clear that doing so would give his fledgling solo career a boost.

Justin and Silas on the way to not the doctor’s office

Justin’s journey to pop icon and Oscar nominee has actually been strangely characterized by the public embarrassments, and even downfalls, of famous women. “Cry Me a River” was an early example of this. Then came the 2004 Super Bowl halftime show, for which Janet “was made a public example of; the new millennium’s modern witch put on trial.” (This Twitter thread is particularly useful for making sense of the timeline of the fallout for Janet, and this report details how since-disgraced television executive, Les Moonves, harboured a years-long grudge against her that he often acted on.) Last summer, when Jessica Biel, Justin’s wife of nearly a decade, was revealed to be an anti-vaxxer, having reportedly not adhered to the standard vaccine schedule for her son, Silas, she was dragged for it online. While that dragging was definitely warranted, strangely absent from much of it was the fact that Justin co-parents the same son, and he never jumped in to defend her (not that he would’ve had a case).

Most recently, Justin was forced to issue a public apology to Biel after he got hammered and was photographed holding hands with Palmer co-star Alisa Wainwright, in what he called “a strong lapse in judgement.”

“This is not the example I want to set for my son,” he wrote.

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