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On This Day in 2002, Justin Timberlake Released a Scathing Pop Hit, Fueling the Fire Around His Breakup With Britney Spears

November 25, 2025
in News
On This Day in 2002, Justin Timberlake Released a Scathing Pop Hit, Fueling the Fire Around His Breakup With Britney Spears

Justin Timberlake made his solo debut in 2002 with the album Justified, recorded during an *NSYNC hiatus, as a bid to emerge as a serious R&B singer. He wanted to shed his boy band image and embrace more blue-eyed soul, which would influence his long-held solo career. His breakout single, “Cry Me A River”, was lauded for its emotional and personal lyrics. But it also served as a point of contention for his ex-girlfriend, Britney Spears.

Spears and Timberlake dated for three years, cultivating a public-facing, whirlwind romance that came to a screeching halt in 2002. They met as pre-teens on The All-New Mickey Mouse Club and became romantically involved in 1999. Spears often praised their deep emotional connection, which came from knowing each other since they were 12. But when “Cry Me A River” subsequently dropped, things quickly got messy.

The pair was constantly hounded in the tabloids, and there wasn’t much privacy for them, as was the nature of the paparazzi in the early 2000s. When they split, Justin Timberlake alluded to the rumor that Spears had been unfaithful.

Speaking with Barbara Walters in 2002, Timberlake addressed the rumors, saying, “We’re not perfect. I don’t judge anybody. It’s just young love. It’s just young love. It was a very intense relationship, that’s for sure.”

However, the music video for “Cry Me A River” made the already touchy subject much worse. The video, directed by Francis Lawrence, starred Timberlake as a jilted man who films himself hooking up with another woman after breaking into his ex-girlfriend’s home. When the ex returns, he stalks her around her house, disappearing before she catches him. But when she goes into her bedroom, the sex tape is playing on her TV.

The Point of the ‘Cry Me a River’ Music Video Was To Drastically Alter Justin Timberlake’s Good-Guy Image

Justin Timberlake’s turn as a weirdo stalker in his “Cry Me A River” music video brought attention to the cheating rumors in his relationship with Britney Spears. The woman who played his ex-lover eerily resembled Spears, although at the time Timberlake denied that the breakup inspired the video.

Spears responded by claiming the video was a controversial publicity stunt, which was apparently what Timberlake was going for. “So he got what he wanted. I think it looks like such a desperate attempt, personally,” she told Rolling Stone in 2003.

Filmmaker Francis Lawrence explained to MTV News in 2003 that Timberlake came to him with a general idea for the video, but essentially let him run wild with it. “[Timberlake] told me what the song was about, but in a [general way] as well,” said Lawrence. “He just said it was a kiss-off song, and so I came up with this idea, and he went for it.”

In 2017, Lawrence looked back on the making of the video, sharing new insights into its legacy. One element both Lawrence and Timberlake liked was that none of the characters in the video came out looking like good people. “[Timberlake is] 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,” said Lawrence. “I was much more interested in seeing the dark, twisted version, and luckily he went for it.”

Beyond all the Britney Spears allusions, the video was successful in transitioning Justin Timberlake from his squeaky-clean boy band image to some sort of hip-gyrating sex god. The difference between “I’ll have your daughter home by 9” and “She thinks I’m sexy when I rev my Harley.” Or something like that.

How ‘Cry Me A River’ Led to Britney Spears’ Response, ‘Everytime’

Britney Spears’ initial response to “Cry Me A River” was, naturally, frustration. But in 2003, she released the song “Everytime” on her fourth album, In The Zone. In comparison to “Cry Me A River,” this song was more of a lament, a quiet regret in the form of a piano-based ballad.

Spears wrote “Everytime” with touring vocalist Annet Artani, with whom she’d become close friends. Artani spoke about the experience to Muu Muse in 2010, claiming that the song was a response not only to “Cry Me A River,” but to things Timberlake was saying in interviews.

“He was getting personal. Here, she had a different type of image, and he was really exposing some stuff that she probably didn’t want out there, and in front of her little sister [Jamie Lynn Spears],” said Artani. “I remember her sister being mortified and her being mortified. I’m sure that that really hurt her.”

For the music video, Spears took her own turn at controversial imagery, although her concept seemed ultimately more involved and a bit more introspective. Spears portrayed a character that deeply mirrored her own life, dealing with overbearing paparazzi and the depressing downside of pop stardom. Critics lauded the video for its references to The Passion of the Christ, the Kabbalah, and stigmata.

Besides its religious imagery, there were initially scenes that alluded to an accidental overdose. When the original concept leaked, it garnered extreme criticism, claiming Spears was glorifying suicide. The concept was changed. Instead of taking pills, Spears’ character falls unconscious in a hotel bathtub from a head wound she sustained from being hit with a paparazzi camera.

A Close Reading of ‘Cry Me A River’ and ‘Everytime,’ and How Britney Spears’ Memoir Put Things Into Perspective

Overall, both “Cry Me A River” and “Everytime” were responses to a deeply emotional breakup from an intense romance. Clearly, the event affected Timberlake and Spears differently. The music videos present two perspectives. One is a man who feels he’s been treated badly and wants to get revenge. The other is a woman who feels overwhelmed by her life in the spotlight and perhaps wants to escape.

Since the early 2000s, Britney Spears has spoken openly about her relationship with Justin Timberlake. In her 2022 memoir The Woman In Me, ghostwritten with journalist Sam Lansky, Spears revealed that Timberlake was actually the one who was continuously unfaithful in their relationship.

“Photographers caught Justin with one of the girls from [British girl group] All Saints in a car,” she wrote. Additionally, she claimed Timberlake persuaded her to get an abortion when she became pregnant. Spears admitted that her innocent image was mostly fabricated—stating that she became sexually active around 14 years old even though publicly she claimed to be waiting until marriage—which put a new perspective on how the public turned on her after her breakup with Timberlake.

Undoubtedly, Spears’ downward spiral was a product of relentless media scrutiny in her youth, and Justin Timberlake’s reaction to their breakup certainly didn’t help. The memoir certainly put Spears’ life into perspective, as much as “Everytime” put “Cry Me A River” into perspective as well.

Photo by Kevin Winter/Getty Images

The post On This Day in 2002, Justin Timberlake Released a Scathing Pop Hit, Fueling the Fire Around His Breakup With Britney Spears appeared first on VICE.

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