Before all the reinventions and reversals, there was “… Baby One More Time”, Spears’s debut single. Undemanding, well served by the lyric “Oh baby”, it wasn’t anything special, but rose above the mulch of the day thanks to two critical elements. The chorus, with its repetition of: “Hit me, baby, one more time”, had an unusually creepy subtext. And someone put the 17-year-old in a sexualised school uniform to shoot the video, all but guaranteeing (in 1999’s comparatively pure popscape) loads of publicity-aiding blather from newspaper columnists and religious groups. Britney had arrived Photograph: PR
Funny to think this once counted, in Britney terms, as controversial, but her world was a gentler place in 2001. For an estimated $50m, Spears was contracted to be a spokesperson for Pepsi. She’d drink it, be filmed drinking it, talk about drinking it, the usual sort of thing, with her image slapped on Pepsi’s cans and bottles for good measure. The only trouble was that Britney liked to drink Coke and couldn’t kick the habit, even after her taste buds became the property of PepsiCo. So in 2003, too often seen cavorting with the wrong kind of can, Pepsi signed up Beyoncé instead Photograph: Startraks Photo/Rex Features
In 2002, MTV’s annual awards fell on the same day as Michael Jackson’s birthday. In a show of cross-generational respect it was arranged that Britney would give a little speech about the senior popstar and present him with a giant cake. Spears, at the microphone, made an offhand remark about Jackson being her “artist of the millennium”, and by the time MJ got to the stage he was given to understand that he was being named just that: artist of the millennium. While Britney danced beside the (now redundant) cake, Jackson spoke movingly about receiving a non-existent award Photograph: Kevin Mazur/WireImage
Was it weird that for years one of the most pressing questions in our culture was: had they? Spears and boyfriend Justin Timberlake, that is: had they done it? Bloody right it was weird, but Spears and Timberlake contributed to the circular speculation as much as anybody – by denying sexual relations in interviews while also giving coy, contradictory hints, and by talking up the virtues of abstinence before behaving like wizened shag-hounds in their respective dance routines and videos. After their break-up in 2002, both parties admitted that, yeah, they’d been doing it the whole time Photograph: Jeffrey Mayer/WireImage
With hindsight, this was as good as the music got for Britney. There will always be those who prefer 2000’s kitsch-bomb, “Oops!… I Did It Again”, memorable for its unbelievably cheesy, spoken-word interlude, riffing on a scene from Titanic. But 2004’s Cathy Dennis-co-penned “Toxic”, No1 on both sides of the Atlantic, is definitely her best single: a proper bit of dancefloor pop, all electro-strings and slurred midnight vocals, good enough to win Spears her only Grammy award to date. No silly outfits, just a great tr... What’s that? She dressed as a sexy air stewardess in the video? Still. Great track Photograph: PR
As cynical as the schoolgirl outfit, it is with reluctance that Britney’s 2003 smooch with Madonna makes this list. But you review her career and there it is, unavoidable: Spears and Madonna on stage at the MTV awards, gyrating to “Like a Virgin” before yielding to each other with all the feigned arousal of student pole dancers to lock lips. “Pop babes’ lezzy kisses,” reported the Daily Star, setting the tone for the subsequent coverage. Spears said Madge had told her: “Just go with it, see what happens.” She did not say whose suggestion it was they behave like the drearily predictable figments of a teenage boy’s imagination Photograph: Win Mcnamee/Reuters
It’s hard to pin the exact moment at which Spears’s life choices veered from capricious to concerning (later to downright distressing) but her 55-hour marriage to a school friend was probably the moment most fans felt the first prickles of worry. On 3 January 2004, led down the aisle by the limousine driver who’d driven her to the venue, Spears wed Jason Allen Alexander, a student and old pal, at the Little White Wedding Chapel in Las Vegas. By 5 January, it was over, annulled by a local judge with both parties’ consent. “A joke [that went] too far,” said Britney’s record label. “Just crazy, man,” reflected Alexander Photograph: Kevin Foy/Rex Features
Spears met Kevin Federline, a pencil-bearded dancer, in a Hollywood club in early 2004 and three months later they were engaged. Within a year, they’d married and had agreed, worryingly, to star in their own reality series called Britney & Kevin: Chaotic (tag line: “Can you handle our truth?”). They had two kids, but in 2006 Spears filed for divorce and an ungainly custody battle followed. Around this time, Federline performed briefly as a professional wrestler and Spears suffered a series of public wobbles. By 2008, Federline was reporting that their relationship had normalised. They now share custody Photograph: Jim Smeal/BEI/Rex Features
Nobody saw this coming, but perhaps we should have, given Spears’s anything-might-happen relationship with the paparazzi in 2007. In October, she ran over a photographer’s foot; the February before, in something of a lifetime’s nadir, she made global news after shaving her head and attacking a pap’s car with an umbrella. What was there left to do? In December 2007, she stepped out with Adnan Ghalib, a Hollywood-based celebrity snapper, originally from Birmingham. Their fling lasted a few months, apparently terminated by Spears after she learned that Ghalib had been selling pictures of her to his agency Photograph: Most Wanted/Rex Features
“Comeback” might be over-egging it, but really, after the late-00s she had, who’d begrudge Britney some gentle success on the musical side of her ledger? Spring album Femme Fatale made it into the top 10 in the UK, hitting No1 in the US. And her summer tour of America, soon to transfer to these shores, was declared “better than even diehard defenders would’ve predicted” by Rolling Stone magazine. Faint praise, perhaps. But in a 13-year career so full of catastrophe, it must count as a highpoint that Britney’s not, for now, doing anything more remarkable than releasing records and dancing about in her skimpy pants of old Photograph: Photonews/Getty Images
