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SARAH DITUM

Being Britney Spears: inside the teen dream that turned toxic

The troubled singer’s new book, The Woman in Me, claims she had an abortion after getting pregnant with Justin Timberlake’s baby. Sarah Ditum charts the pop-powered rise and catastrophic fall of the last star before the social media age

Left: Britney Spears in the video for Baby One More Time, October 1998. Right: Instagram videos show her dancing with fake knives, September 2023
Left: Britney Spears in the video for Baby One More Time, October 1998. Right: Instagram videos show her dancing with fake knives, September 2023
AVALON
The Sunday Times

It starts with a video: a loafer kicking against the leg of a school desk; a pencil tapping on a notepad; a clock ticking towards three and a girl watching it. Then the bell tears apart the quiet and pulsing piano chords break into the soundtrack. “Oh baby, baby,” the girl sings, in a way that falls somewhere between abject and accusing, “how was I supposed to know?” Her white shirt is tied up to reveal her midriff and unbuttoned to below her cleavage.

The song was released in the US in 1998 and was already a hit there, but when I first see it in the UK it’s February 1999. I’m 17, the girl in the video is 16, and I can’t look away. Baby One More Time is a great song, but more than that it’s an extraordinary arrival: every component of the Britney persona is established by the end. I’m immediately and for ever a Britney Spears fan.

To the tween girl sector she was the idealised version of what they might become postpuberty. To men she was the perfect instance of pliant femininity. And to those who, like me, had crossed the boundary of female adolescence, the Disney Channel’s former All-New Mickey Mouse Club presenter offered a model for the scrutinised life that seemed an inevitable aspect of being female.

1993-95: front right, in The All-New Mickey Mouse Club, with Ryan Gosling, front left
1993-95: front right, in The All-New Mickey Mouse Club, with Ryan Gosling, front left
DISNEY

Britney, with her unimpeachable command of the grammar of the male gaze, appeared to have mastered the business of being an object. She was, whether instinctively or calculatedly, an expert in being looked at.

When her debut album came out (also called Baby One More Time), the US sleeve showed her kneeling and looking up at the camera, head cocked ingratiatingly, legs slightly parted so you could almost (not quite) see up her denim mini. I didn’t know it yet, but the Upskirt Decade had begun. And at some point the girl’s perfectly controlled appearance of losing control would be replaced by genuine, terrifying helplessness. Britney would be famous in a way that no pop star before had ever been.

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This is not because she would be more successful than her predecessors, although she was extremely successful. It’s because she was calibrated for a kind of celebrity that was about to cease to exist. The fame she was working towards with the release of Baby One More Time was mediated through TV, radio, newspapers and magazines, and calculated in CD sales. It would bear almost no relation at all to the fame she had to negotiate over the next ten years because, shortly after Britney’s arrival, the internet happened. She was simultaneously the next big thing and the last star of a dying age.

October 1998: aged 16 and dressed as a schoolgirl in the Baby One More Time video
October 1998: aged 16 and dressed as a schoolgirl in the Baby One More Time video
INSIGHT

The year 1999 was the most successful on record for the US music market, with a total value of $14.6 billion. Within that historic high, Britney’s debut album was one of the standouts. But in June of the same year the peer-to-peer file-sharing service Napster was launched, enabling anyone with an internet connection to download anything they wanted, provided someone else on the network had made it available.

Suddenly record labels were competing not just against each other but against their own products being offered without charge. The industry went into immediate decline and over the next ten years its value almost halved: by 2009 US music sales totalled a mere $7.8 billion.

The Baby One More Time album sold 14 million hard copies in America; Britney’s 2007 album, Blackout, sold just one million, and while that partly reflected a dip in her popularity, the biggest-selling album of the same year sold only four million units in total. The traditional economics of pop music had flipped.

January 1999: her first album sold 14 million copies in the US
January 1999: her first album sold 14 million copies in the US

With CD sales on the slide, concert tickets would have to compensate. In the Eighties and Nineties Madonna had averaged one big tour for every two albums. Britney toured every album. Between 1999 and 2004 she played 357 dates, 122 of them in 2000, not including her other promotional duties.

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Every tour required choreography and rehearsals. Every concert meant hours of travel and sleeping in another strange city. And in between this she had to record the albums that justified the live performances. It was a punishing work rate for anyone, never mind someone as staggeringly young as Britney was. But it was the only way for a pop star to be profitable.

All the same, Britney was a phenomenon and rapidly became established as a peer of music’s biggest names. In 2001 she was invited to duet with Michael Jackson at a concert to celebrate 30 years of his solo career. Two years after that she performed with Madonna at the 2003 MTV Video Music Awards.

January 2001: with her first boyfriend, Justin Timberlake
January 2001: with her first boyfriend, Justin Timberlake
GETTY IMAGES

These events fixed Britney in the pop royalty line of succession, but there was benefit in both directions: she was so big by then that claiming her as an heir was a way for these acts to assert their power. The VMA performance in particular had the feel of a reigning mafiosa anointing a successor. At the climax Madonna bestowed a kiss on the lips to Britney. It was a huge moment: although Madonna repeated the trick with Christina Aguilera on her other side, the cameras had already cut to the audience’s dazed reaction — lingering on NSync’s Justin Timberlake, Britney’s former boyfriend and fellow pop sensation.

The Oops I Did It Again album, released in 2000, had teased a more provocative Britney, one who declared herself “not that innocent” after all, although she still stopped short of claiming any sexual experience. Britney, in 2001, went further: the lead single, I’m a Slave 4 U, was an orgy of panting eroticism. Even so, nymphette elements remained, as the ballad I’m Not a Girl, Not Yet a Woman made explicit. In the first eye-opening snippet from her memoir, The Woman In Me, which is published on Tuesday, Spears claims that she had an abortion after getting pregnant with Timberlake’s baby. “If it had been left up to me alone, I never would have done it,” People magazine quotes her as writing. “And yet Justin was so sure that he didn’t want to be a father.” Timberlake has not commented on the abortion.

Her first tour had been as an opening act for NSync. But their roles quickly reversed. When both acts made their VMA debut in 1999, the classroom-themed staging turned the boy band into an audience for her strutting and teasing; when she cooed, “I’d like to introduce to you some friends of mine,” it was obvious which act held seniority. Britney and Justin were a pop power couple but there was a hierarchy: the queen of teen and her prince consort.

September 2001: performing at the VMAs with an albino python
September 2001: performing at the VMAs with an albino python

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When he and Britney split up in 2002 and rumours of her infidelity broke in the press, an opportunity presented itself. Timberlake could purchase his rebirth with a virgin sacrifice — or, rather, by sacrificing the myth of Britney’s virginity. After years of gentlemanly discretion, he now couldn’t stop running his mouth all over the media.

The centrepiece of the Timberlake reinvention came with his second solo single, Cry Me a River, released in the US in November 2002. The song is addressed to an unfaithful ex — widely assumed at the time, and later confirmed by the producer Timbaland, to be Britney Spears. In the video Timberlake watches his ex leave her house, breaks in and shimmies about inside it, dressed throughout like Tony Curtis in The Boston Strangler; at the end the ex comes home and Timberlake watches her taking a shower.

September 2001: performing with Michael Jackson
September 2001: performing with Michael Jackson
MISSION PICTURES

The video was a watershed for the reputations of both Britney and Timberlake. It marked him as a wounded bad boy, casting off his NSync stigma with no detrimental effect on his heart-throb status. Britney was turned into the villain — a faithless woman who could be rightfully shamed in regular rotation on MTV.

On the home front things were equally complicated. In Britney’s early career her mother, Lynne, was an omnipresent figure, playing chaperone and acting as the guarantor of her daughter’s purity. Mother and daughter even produced two books together: the non-fiction Britney Spears’ Heart to Heart in 2000, telling the “inspiring story of how one little girl from a small town in the USA turned into a musical phenomenon”, and a novel called A Mother’s Gift in 2001, about a girl with a “dream of pursuing a singing career”. These books were both brand extension and brand reinforcement.

In the first place they existed to draw more money from Britney’s fans. In the second they existed to prove that Britney really was a good girl who loved her “mama”, and therefore a safe role model for the tween market.

March 2003: the singer with, from left, her father, Jamie, brother, Bryan, sister, Jamie Lynn, and mother, Lynne
March 2003: the singer with, from left, her father, Jamie, brother, Bryan, sister, Jamie Lynn, and mother, Lynne
WIREIMAGES

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Still, there were hints that everything was not quite right in the world of Britney. In February 2003 Star magazine splashed an allegation of her taking cocaine in a nightclub bathroom — something Britney initially denied through a representative, but responded to more ambivalently in a follow-up interview with the magazine when she said, “Let’s say that you reach a stage in your life where you are curious.”

The 2003 VMA performance with Madonna, rather than heralding a return to Britney’s self-possessed prime, turned out to be the last high before a precipitous slide; she wouldn’t be seen at the awards again until 2007. The constant stream of paparazzi shots showing her going in and out of nightclubs, generally appearing in some state of intoxication, were one thing. More concerning was the incident in January 2004 when she married her high-school friend Jason Allen Alexander in a Vegas quickie; 55 hours later the union was dissolved. The terms of the annulment included the troubling statement that Britney “lacked understanding of her actions, to the extent that she was incapable of agreeing to the marriage”.

August 2003: kissing Madonna on stage at the VMAs
August 2003: kissing Madonna on stage at the VMAs
WIREIMAGE

Months later she married again, this time to the dancer Kevin Federline. They had two sons together: Sean, now 18, and Jayden, 17. This union was chronicled in a 2005 reality series called Britney and Kevin: Chaotic, based on camcorder footage filmed by Britney herself. It ran for five episodes and ensured that any vestige of glamour clinging to Britney was extinguished. People already believed her to be “white trash”. Chaotic only confirmed this.

In a further dent to Britney’s reputation, celebrity blogging was just beginning to explode around this time. Perez Hilton had started his first blog in late 2004, but in 2005 his antagonistic approach to the stars he covered gained mainstream recognition. He made a trademark of calling female celebrities “sluts” and Britney gave him an especially rich seam of material.

Between 2005 and November 2007 Britney released no new studio albums and performed just nine times. She existed not as a pop star but as a tabloid presence. Her marriage to Federline unravelled within two months of the birth of Jayden, their second child, in 2006. There was an abortive stint in rehab. She lost weight, gained weight, and was accused of being a “bad mother” when she was photographed driving with her elder son, Sean, on her lap. In 2007 she lost custody of her children.

January 2004: a quickie Vegas wedding to Jason Alexander — annulled 55 hours later
January 2004: a quickie Vegas wedding to Jason Alexander — annulled 55 hours later
SPLASH NEWS

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There was also the concerning presence of a man called Sam Lutfi, her manager, whom Britney’s mother accused of drugging and controlling the singer. Lutfi denied this, saying through his lawyer that he had “merely responded to cries for help”; Britney was granted a series of restraining orders against him.

And in February 2007 she walked into a hair salon in Los Angeles, took up a set of clippers and shaved her head. A few days later she was photographed, shorn-headed and wide-eyed, taking an umbrella to a paparazzo’s car outside a petrol station. Britney had been the avatar of femininity in the new millennium and her flowing hair was integral to that. The hairdresser who spoke to Britney in the salon recalled her saying, “My mom is going to freak.”

December 2004: with her new husband, Kevin Federline
December 2004: with her new husband, Kevin Federline
WIREIMAGE

Britney also spoke to a tattoo artist in the salon, who asked why she’d shaved her head. “I don’t want anyone touching my hair. I’m sick of people touching my hair,” was Britney’s reply. Lutfi offered a more prosaic explanation years later — that by destroying her hair, Britney was destroying evidence that could be used in compulsory drug testing. But the iconography of the act was profound. Consciously or not, this was a rebellion against the girlish compliance and availability that Britney had been groomed to perform.

Even when Britney seemed to be rejecting her persona, though, she continued to be relentlessly documented: the bodyguards who were supposedly tasked with shielding her from the paparazzi chatted with photographers while all this happened, according to the hairdresser.

February 2007: shaving her head
February 2007: shaving her head
THE MEGA AGENCY

Some on the press side have claimed that the intimacy between Britney’s camp and the paparazzi was longstanding, with “her people” passing on information about her whereabouts. Perez Hilton even alleged that Britney herself was sending in the tips. It is true that celebrities have an awkward symbiosis with the paparazzi and many will develop relationships with photographers who follow them day after day — Britney even dated one of hers for a time.

But why conduct the head-shaving in public at all? If Lutfi’s theory was right, it would surely have made more sense for Britney to do this at home. Perhaps, having been on display ever since she was a child, she needed to be seen in order to feel her revolt meant anything. Or perhaps this was simply the way she had accepted her life should be. The head-shaving was the moment she began to be described not merely as low-class or slutty, but as mad.

February 2007: using an umbrella to attack a photographer’s car
February 2007: using an umbrella to attack a photographer’s car
X17 AGENCY

In September 2007 — her hair long and blonde again, thanks to extensions — she made her return to the VMAs. What was billed as a glorious comeback turned into a shambles. Britney fluffed her choreography and looked vacant, and even her body was declared substandard; there were reports that she had called herself a “fat pig” while watching the footage. The X Factor judge Simon Cowell considered the performance potentially career-ending. “She wasn’t ready for that show in every possible way,” he told The Sun.

Somehow, while all this was happening, she was also recording what would widely come to be considered her best album. From its substance abuse-baiting title onwards, Blackout tackled Britney’s tabloid image directly. Released in November 2007, its standout track is the electropop assault Piece of Me. The song’s title, in classic Britney style, is ambivalent, both a challenge and a surrender. In the video we see Britney rewriting her own press and taking revenge on her tormentors with the help of a squadron of Britney lookalikes.

October 2007: photographers mob Britney’s car as she fights for custody of her children
October 2007: photographers mob Britney’s car as she fights for custody of her children
GETTY IMAGES

In January 2008, less than three months after Blackout’s show of defiance, paramedics were called after an incident at her home and Britney was removed to a psychiatric ward. Her father Jamie, acting with the support of her mother despite their divorce, petitioned for Britney to be placed under a conservatorship and for the next 13 years everything about Britney — her career, her finances, who she saw, even what she did with her body — would be controlled by him.

According to lawyers acting for Britney, Jamie Spears would receive more than $6 million through the conservatorship. Another significant beneficiary was the media, which had a shocking new twist for the ultimate celebrity narrative.

September 2007: back at the VMAs, but her performance is lacklustre
September 2007: back at the VMAs, but her performance is lacklustre
FILMMAGIC

From the outside Britney’s conservatorship appeared to be a great success. In November 2008 Us magazine announced that she was “officially in comeback mode”. The same month MTV broadcast a fly-on-the-wall documentary called Britney: For the Record. It showed the public a Jamie Spears who was devoted to the welfare of his daughter and a composed Britney who was ready to acknowledge her past mistakes. “I’ve definitely grown up. Big time,” she says. “I had totally lost my way. I lost focus. I lost myself. I had that type of nature within me that wanted to rebel.”

There were irregularities — she appeared vacant and inarticulate during a 2012 stint as a judge on the US version of The X Factor and was not invited back, but overall the narrative of Britney reborn held sway.

September 2012: on the US X Factor with Simon Cowell
September 2012: on the US X Factor with Simon Cowell
PLANET PHOTOS

Yet there was a problem with this, although many chose not to acknowledge it. If Britney really was better, what was the justification for her father’s continued ownership of her life? And if Britney was still the fragile young woman everyone had watched coming apart in 2007, how could it be OK for her to be put on public display with each performance? There was no way to ask what Britney truly thought because the terms of the conservatorship meant that everything she said to the media had to be filtered through her father.

By 2020 fans had started to express concern for her under the banner #FreeBritney. And behind the scenes Britney brought legal challenges to the conservatorship, beginning in 2014. In 2016 a court investigator reported that “she feels the conservatorship has become an oppressive and controlling tool against her”.

July 2019: with her boyfriend Sam Asghari. They married in 2022 but he has now filed for divorce
July 2019: with her boyfriend Sam Asghari. They married in 2022 but he has now filed for divorce
FILM MAGIC

In 2020 her attorney told the judge that Britney was “afraid of her father”. None of this was enough to bring the conservatorship to an end, however. Britney’s predicament was that, having been classified as mentally unwell, any objection she made to the constraints on her liberty could be dismissed as symptoms of her illness.

It was only after the 2021 New York Times documentary Framing Britney Spears that popular opinion swung fully behind the idea that her situation was intolerable. In a new hearing that year Britney delivered a devastating testimony of being, in her words, “enslaved”. She said she had been “forced” to tour in 2018 and that her most private decisions had been dictated for her, including whether she could get married or conceive a child — her father, she claimed, had refused permission for her IUD to be removed. He denied this.

September 2021: fans show support as a conservatorship hearing takes place
September 2021: fans show support as a conservatorship hearing takes place
GETTY IMAGES

She was compelled to take lithium, she said, which made her feel “drunk”. She had no privacy from the people in her father’s employ: “They watched me change every day — naked — morning, noon and night.” Perhaps the most painful detail was the disassociated way she spoke about herself. “My precious body,” she said, “who has worked for my dad for the past 13 years, trying to be so good and pretty. So perfect.”

The court granted Britney her freedom. At 39, the woman-child who had never lived an adult life was able to begin again. And while she blamed her family for exploiting her, she was also angry about the way her situation had been covered in the media. “I feel like America has done a wonderful job at humiliating me and is it honestly legal to do that many documentaries about someone without their blessing at all?” she wrote in a 2022 Instagram post. That year she married the fitness trainer and model Sam Asghari. He filed for divorce two months ago after 14 months of marriage.

Britney credited her emancipation to her fans. Fame had come close to destroying her and yet fame had given her love and support she had not experienced from her own family. In the hypocrisy and cruelty of her treatment the public life of women in the Noughties was defined. Her debut had launched her into a kind of celebrity for which no one could have been prepared, one shaped by forces that few could have foreseen — least of all a 16-year-old. “Oh, baby, baby,” she sang in 1998, the Upskirt Decade as yet an unimagined prospect, “how was I supposed to know?”

© Sarah Ditum 2023. Abridged extract from Toxic: Women, Fame and the Noughties by Sarah Ditum (Fleet £22). Buy at timesbookshop.co.uk. Discount for Times+ members

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This article was originally published on Wednesday October 18