The Ballad(s) of Justin and Britney, Vol. 1: ‘Cry Me a River’

Sydney Urbanek
16 min readMar 19, 2020

“The bridges were burned / Now it’s your turn, to cry”

On “The All-New Mickey Mouse Club” (MMC)

This essay is the first of a two-part series on the music videos that came out of the Justin Timberlake/Britney Spears breakup. (Click here to read “The Ballad(s) of Justin and Britney, Vol. 2: ‘Everytime.’”)

2007 was particularly good to Justin Timberlake. He spent most of the year touring in support of his second studio album, FutureSex/LoveSounds, which spawned four number-one singles — “SexyBack, “My Love,” “What Goes Around… Comes Around,” and “Summer Love” — and ultimately won him as many Grammys. By the time he sat down with Oprah Winfrey on her namesake show in September, he’d also appeared on the TIME 100, aired his tour as an HBO special, starred in Shrek the Third, and won an Emmy for “Dick in a Box.” In the Oprah Winfrey Show episode that aired on September 19, Oprah asks Justin about staying grounded, the necessity of hard work, and how he’d been “living that celebrity life” — Oprah’s words, not his — since he was on The All-New Mickey Mouse Club (MMC) in his preteens. But there was an elephant in the room: 2007 had not been so good to fellow Mouseketeer Britney Spears, whom Justin had dated from roughly 1999 to 2002.

“I wouldn’t be doing my job if I didn’t ask the Britney question,” Oprah says.

“What question is that?” Justin responds amid audience giggles.

“What do you think is going on with Britney?”

On “The Oprah Winfrey Show” in September, 2007

Justin firstly tells Oprah that he doesn’t really know, and it’s worth noting right off the bat that, for all our speculating at the time, none of us actually did. Coverage of Britney’s so-called breakdown in 2007 was not only severely lacking in compassion, as Roslyn Talusan argued for Flare last year, but also missing crucial context. Retellings don’t tend to include, for example, that Britney’s aunt had died just weeks before the infamous head-shaving incident in February, or that she thereafter described that night as “a little bit of rebellion” — framing pretty different from “THE NIGHT BRIT CRACKED.” A week and a half before Justin’s Oprah interview, Britney had opened the MTV Video Music Awards (VMAs) with an admittedly hard-to-watch performance of “Gimme More,” and the world was talking about February all over again. Justin goes on to tell Oprah:

I haven’t spoken to her in years. I mean, there’s no ill will. I have nothing but love for her. […] We were teenagers, you know. And I think that’s basically the best way to describe what happened to us, and I think she’s a great person. I don’t know her as well as I did. […] What I do know about her is that she has a huge heart. She is a great person.

Though Oprah lets him off the hook at this point, there were several holes in his answer. Justin had positioned himself in that moment as someone who didn’t think about Britney anymore. They were teenagers, you know. While that was true for a lot of their relationship, both parties turned 21 the year of their breakup; they were very much adults, if young ones. He didn’t know her as well as he did. Fair enough, but such distance hadn’t prevented him from mentioning Britney incessantly following the 2002 split. To her apparent mortification, he frequently blabbed about their sex life in public and took shots at her career moves (something he appears to have done as recently as 2018). Six months after his interview with Oprah, he’d allude to Britney twice in a speech inducting Madonna into the Rock and Roll Hall of Fame. “The world has always been full of Madonna wannabes, and I might have even dated a couple,” he joked, five weeks after Britney was placed on a “mental evaluation hold” at UCLA Medical Center. He brought up their sex life yet again on Saturday Night Live the next year.

Which brings us to another questionable part of Justin’s answer: that he had nothing but love for Britney. That narrative was at odds with the one that had been fuelling his solo career thus far.

“M-I-C-K-E-Y M-O-U-S-E”

Here’s a truncated version of Justin and Britney’s relationship timeline. Both had been on TV since 1992, when they individually competed on Star Search. In 1993, they joined the cast of MMC (as did Ryan Gosling and Christina Aguilera). Justin has said that he “was infatuated with [Britney] from the moment [he] saw her,” and Britney has said that she had her first kiss with him around this time. Justin and Joshua “JC” Chasez, himself a Mouseketeer since 1990, would later make up two-fifths of *NSYNC, which released its self-titled debut album in 1997. Britney joined *NSYNC’s Second II None Tour as a supporting act in 1998, and released her own debut, …Baby One More Time, in 1999. By the end of 2000, *NSYNC was promoting its second and ultimately most successful studio album, No Strings Attached (2000); Britney was breaking records with her own sophomore effort, Oops!…I Did It Again (2000); and Justin and Britney were confirmed to be dating.

At the American Music Awards on January 8, 2001

Beyond their shared celebrity and work history, the pairing made a lot of sense. Both artists were from the South, were often described as perfectionists, and danced as well as they sang. Once they went public in 2000, they really went public: they openly had hokey nicknames for each other, appeared in matching denim-on-denim outfits at the American Music Awards, and flirted on stage during the Super Bowl halftime show. Britney practically beams in interviews about Justin from this time; there’s lots of talk about how seldom they get to see each other, how there’s nothing better than a movie night on the couch, and how she’d “love to be with him forever.”

Then, something happened in early 2002. It was rumoured to be an affair on Britney’s part, but — and I’ll continue to stress this — we the public don’t (and shouldn’t claim to) know the full story. Immediately after the breakup, *NSYNC went on hiatus and Justin went into the studio to record his first solo album, Justified (2002). It was finished in six weeks, with much of it produced by Timbaland and the Neptunes (aka Pharrell and Chad Hugo). The album’s debut single, “Like I Love You,” was released in August and peaked at #11 on the Billboard Hot 100 chart. For a star as big as Justin was, the song had underperformed. There wasn’t anything wrong with it, nor with its Diane Martel-directed video (even if Justin arguably didn’t need to wear a 7/11 graphic tee for his dance sequences in a 7/11 parking lot). The problem, as the BBC put it in their brutal coverage of the song’s chart performance, was Britney-related:

Justin Timberlake’s solo debut has failed to knock rapper Nelly from the top of the UK singles chart. The N’Sync singer’s Like I Love You was heavily tipped to shoot straight to the top of the charts. But the Michael Jackson-influenced track could not muster enough sales to beat Nelly’s worldwide hit Dilemma, which features Destiny’s Child singer Kelly Rowland. While N’Sync have achieved huge success in the US, in the UK Timberlake is best known as the former boyfriend of pop superstar Britney Spears.

Justin’s star persona had indeed been inextricably linked to Britney’s for a solid two years. She was the global superstar of the duo, the one that tabloids actually cared about at the time—in the sense that she sold lots and lots of magazines, that is.

With his mother, Lynn, on ABC’s “20/20” in early November, 2002

The album wasn’t set to be released in full until early November, which gave Justin a chance to course-correct. Ahead of its release, he spoke to Barbara Walters for a televised interview in his family home in Tennessee. “The impression is that Britney did something very bad that hurt you; she had a relationship with someone else. Was there an incident?” Walters asks Justin during the episode. “I promised to her that I wouldn’t say specifically why we broke up,” he responds, implying that such information was damning in some way. When Walters asks whether the two really kept their virginity pledge — Britney wore a purity ring throughout their relationship — he sarcastically responds, “Sure,” and then laughs. He’s otherwise careful to present himself as sensitive, someone for whom it all comes back to the music; that other stuff was just noise. (When Walters asks whether he’s seeing anyone new, he replies, “If you really want to know who my girlfriend is, it’s those 13 songs on that CD.”) An obvious effort has also been made to establish him as a mama’s boy. When Justin “cried himself to sleep” after the breakup, his mother, Lynn, cried with him. “It was tough for both of us ‘cause I can’t stand to see him hurt,” Lynn tells Walters, her eyes welling up with tears.

“What do you most want people to know about your son?” Walters asks her later in the interview.

“That he genuinely, deep down inside, is a good person.”

In less than ten minutes, Justin assumes the role of heartbroken wunderkind, and Britney the cheater who wasn’t as pure as she’d been telling everyone. If this was to be his new strategy, the fact that Britney’s brand had become increasingly risqué over the preceding couple of years would only work against her.

Britney with a different snake at the MTV VMAs in on September 6, 2001

Justified came out on November 5, the day after the Barbara Walters interview aired, with “Cry Me a River” becoming its second official single a few weeks later. The song was “a spiteful ballad about an unfaithful lover,” clearly alluding to the rumours that had swirled around the breakup back in March. In a 2011 E! True Hollywood Story episode about Timbaland, it was finally confirmed that the song was about Britney. “[Justin] went to a concert and saw Britney and Britney talked about him in the show,” Timbaland explains. “And he was pissed.” Justin told GQ in 2006 that he “felt like [Britney] had a couple opportunities to just sort of stick up for me, and she didn’t, which is fine. But at that time, you know, I fought back.” The former couple had some kind of heated phone call following the 2002 concert, after which Timbaland remembers Justin storming into the studio. Angry and inspired in equal measure, he started to mumble-sing the opening lines of the song — “You were my sun, you were my earth” — so Timbaland left him alone for an hour and a half with some beats. He returned to find “Cry Me a River” more or less finished. Both men are credited as its writers, as is producer Scott Storch.

The video for the song premiered on MTV’s TRL on November 25, the same day that the single was sent to radio. Justin called in — he’d broken his foot and couldn’t make it in person, per his “physician’s recommendations” — and stressed that the video wasn’t about Britney, but about him. He also told host Carson Daly that he’d had little to do with its creative concept, simply approving director Francis Lawrence’s treatment because he “thought it was really cool.”

“I’m a Slave 4 U” (2001)

In a more recent interview, however, Lawrence described 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.” Lawrence had made Britney’s “I’m a Slave 4 U” video the previous year, which made him entirely familiar with her and her developing come-hither brand; he’d literally played a role in shaping it. (The two have since worked together on “Circus” [2008].)

Even though Justin wouldn’t admit to the song being about Britney, the video made it so that he didn’t have to. It begins with a blonde (Lauren Hastings) in a newsboy cap — a then-staple of Britney’s wardrobe — and a male companion leaving a mansion in the pouring rain. They’re shown largely in the reflection of a car’s side mirror: they’re being watched, but we don’t know who the watcher is at first. The couple pulls out of the driveway in a different car, still under surveillance by the first. As soon as they’re gone, the window on car A rolls down to reveal that it’s occupied by Justin, with Timbaland in the driver’s seat. A fleeting shot also tells us that there’s a hot brunette (Kiana Bessa) in the back. Whatever will take place over the next few minutes is not only premeditated but a concerted effort between multiple people.

“You were my sun, you were my earth”

Once the coast is clear, Justin scouts the grounds of the mansion. He smashes a window and lets himself in, stepping through the broken glass as the song’s first chorus comes to an end. If it wasn’t yet obvious that this is a revenge story, presumably for all the crying himself to sleep that Justin did, the chorus remedies that: “The bridges were burned / Now it’s your turn, to cry / So cry me a river.” From inside the house, he opens the front door and grabs a small fairy statue to use as a doorstop. Some fans have read this as a reference to the fairy tattoo on Britney’s lower back; it might be one of the “details” that Lawrence was referring to. Then comes the video’s only dance break. Justin makes his way through the house via gravity-defying movements — there were dancers in green-screen suits that helped him out — and trashes nothing else but a framed photo of a couple, which he kicks towards the camera. Anyone watching a Justin Timberlake video in 2002 would’ve expected there to be dancing, but under these circumstances, it helps to establish his dominance and familiarity in this house that isn’t his own. His plan is evidently not to get in and get out, nor to leave no trace.

A culturally important lip bite

From inside the car, Timbaland gestures to the brunette, and she makes her way to the bedroom to meet Justin. With a video camera that Justin has grabbed out of a drawer — he knows this house, after all — they film themselves making out. (If they do more than that, we never see it.) Many of the images in “Cry Me a River” are mediated ones — reflections in mirrors, video footage, framed photographs, and so on. This was a couple whose relationship had played out largely in the public eye, for all to see and weigh in on, so it’s more than likely that this was an intentional creative choice made on Lawrence and/or Justin’s part.

Two-thirds into the video, car B suddenly pulls back into the driveway. The brunette leaves through the broken window; Justin stays and hides in the house. Timbaland, meanwhile, rubs his hands together from car A: “The damage is done, so I guess I’ll be leavin’.” Looking at the lyrics on their own, such damage refers to whatever Justin’s ex did wrong — whatever it was that precipitated the breakup. In the video, however, it becomes about his retaliation. The blonde enters the house by herself, and Justin trails her as she walks through it, reaching for — but never quite touching — her hair (something that Buffalo Bill literally does to Clarice during the climax of The Silence of the Lambs [1991].)


From here, things get more troubling. Justin hides as the blonde undresses for the shower. He then watches her shower, putting his hands on the glass while her back is turned. Lawrence has said that he was worried about Justin’s acting abilities, but was ultimately “knocked out by his performance in that close-up where he looks hurt and distressed and nervous.” (Ah, yes, Justin’s hurt and distress and nervousness in this scenario.) As the song wraps up, the blonde senses that something’s off, quickly grabbing a towel and exiting the shower. Justin’s gone, but the home movie that he made with the brunette is playing on the television. This is the video’s final shot; Justin is left with the last word, and his ex is left with the terrifying knowledge that he was in her home without her awareness or consent. She’ll presumably discover her broken window and picture frame in due time. After the video’s TRL premiere, Carson Daly commented that Justin’s character in the video has “an American Psycho feel,” to which Justin replied, “Hey man, I’m crazy.” According to Lawrence, that vibe was intended from the beginning:

He’s stalking around in the rain, wearing a hood to cover himself up, breaking into someone’s house — I mean, it’s all very violating and creepy. He’s getting revenge and he’s obviously not in a healthy sort of place, but I didn’t want to see a sentimental take on the song — I was much more interested in seeing the dark, twisted version, and luckily he went for it.

Justin apparently wasn’t the first artist to whom Lawrence had offered the video concept, but he was the first to agree to it, embracing it “full-on.”

:/ cont’d

Recall that in his 2007 interview with Oprah, Justin says that he hadn’t spoken to Britney in years. He didn’t really need to if he could communicate with her through his creative output. Case in point: he was currently promoting another infidelity ballad, “What Goes Around… Comes Around,” and performed it on Oprah that day. Though the song was officially inspired by a friend’s breakup, it exists because Justin told the FutureSex/LoveSounds producers that he wanted to “do another ‘Cry Me a River.’”

Scarlett in “What Goes Around… Comes Around” (2007)

The “What Goes Around… Comes Around” video was written by Nick Cassavetes and directed by Samuel Bayer, and is similarly aimed at an unfaithful blonde, this time played by Scarlett Johansson. It has a sequence where Johansson’s character pretends to drown for attention, putting it in conversation with Britney’s “Everytime” video, the subject of the next essay in this series. The title of Justin’s song was also stylized with an ellipsis. He’d never done that before and has never done it since; Britney, on the other hand, was known for it, as with “…Baby One More Time” or “Oops!…I Did It Again.” No matter who the song was truly inspired by, the optics of him performing lyrics like “Tale as old as time girl, you got what you deserved,” over and over as his ex-girlfriend was losing custody of her children, were arguably very bad.

But what message(s) had “Cry Me a River” sent back in 2002? Though Justin had promised not to share with the world why he and Britney broke up, the video established him as a victim and her as a cheater. And regardless of whether and to what extent that was based in any fact, it was treated like an official statement because neither star would share any details with the press.

“Since U Been Gone” (2004)

To be clear, there’s nothing wrong with feeling bitter about the way a relationship ended, nor expressing said bitterness in a music video. (This is how most people were introduced to Alanis Morissette.) It’s also better to play out a revenge fantasy artistically than in real life, period. (Even Kelly Clarkson once went for a post-breakup home invasion concept, if a very different one.) “Cry Me a River” didn’t target some faceless ex, though; it specifically targeted Britney Jean Spears, and made a point of using her likeness to do it. The shower voyeurism turned this indignity into an inherently gendered one: Britney’s stand-in is exposed and vulnerable in her own home, the implication being that she brought this threat upon herself. In fact, Justin’s character is so sure that she deserves it that he happily outs himself as the intruder. He also has a team of people helping him, prophetically indicating that Britney probably had more to worry about than simply Justin. If he plays a fantasy version of himself in the video, one could read Timbaland as representing the music industry at large, and the brunette the rest of the world.

This takes on new meaning once you learn about the phone calls that took place after the video had been filmed. Justin reached out to Britney to let her know that her likeness had been included, but withheld any details. It reportedly got slipped in” to a longer conversation they were having, and Britney remembers Justin insisting that she didn’t need to worry. But Jive Records was worried, especially as their shared label. Lawrence recalls there being “momentary pressure from the ‘other party’ that didn’t last long”:

[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.

It turns out that Jive had contacted Britney, who gave the label her approval. “I had the power to say no to the video. But I didn’t, because I thought, ‘Hey, it’s your video,” she said a year later. But she hadn’t actually seen it, nor apparently been told anything about its plot.

On ABC’s “Primetime” in November, 2003

On premiere day, Britney was on vacation. “Someone called me and told me that it was gonna come on,” she explained to Diane Sawyer in November of 2003, the same week that she released her fourth studio album, In the Zone. “I watched it and I was kind of in denial.” Anyone who’s dated an artist of some kind lives with the knowledge that they could pop up in a work of art one day. To not only pop up but pop up the way Britney did would upset just about anyone. When Sawyer asks in the same interview whether there’s any weight to the claims implied in the song and video, Britney responds, “I think everyone has a side of their story to make them feel a certain way. And I’m not technically saying he’s wrong, but I’m not technically saying he’s right, either.” Justin was naïve if he didn’t think that Britney would make her own side known.

Click here to read “The Ballad(s) of Justin and Britney, Vol. 2: ‘Everytime.’”

If you enjoyed this essay, you might also enjoy my newsletter.