'Oops, I Did it Again': Ten songs that showcase the musical evolution of Britney Spears

The US pop star is the subject of a harrowing new documentary

US singer Britney Spears helped define the pop music sounds of the early 2000s. Courtesy JIVE Records

Pop star Britney Spears is back in the headlines.

A New York Times documentary released this week is providing riveting insights into her music career, controversial relationship with her father and the machinations of an unforgiving music industry.

While Framing Britney Spears makes for some harrowing viewing, the documentary has also sparked a reappraisal of Britney's work, with a new generation of fans checking out her song catalogue on streaming sites.

They will find a lot of good material on offer. Since her emergence 22 years ago, Britney has built an impressive body of work that not only helped define the pop sounds of the early 2000s, but also ushered in the dance music wave dominating the charts and festivals today.

Her work also provides an unvarnished look into her innermost thoughts during what went on to become a tumultuous career.

From the innocent sounds of ... Baby One More Time to the angry defiance of Piece of Me, Britney's catalogue tells the story of a teenager's public transition to adulthood with all the joys and pain that comes along the way.

Here are 10 songs that best showcase that journey.

1. ‘... Baby One More Time’ (1998)

What an arrival: Britney transitioned effortlessly from Disney children’s television star to pop music stardom with one of the all-time greatest debut singles.

The first of many successful partnerships with Swedish producer Max Martin, the earworm is built upon brilliantly ascending melodies that lead to an explosive chorus straight out of the Abba handbook.

2. ‘Sometimes’ (1999)

A major theme throughout Britney’s career is that pull between youth and adulthood. This is why each album is packed with both playfully upbeat tracks and heartfelt balladry.

Sometimes is good example of the latter, an uplifting and glossy ballad where Britney admits to being a little complicated. Just how deep that feeling ran would be proven years later.

3. 'Oops!... I Did It Again' (2000)

Britney announced herself as a diva in waiting with this sublime piece of pop music. More than the smooth hooks, what makes this song brilliant is the production from Swedish pop-meister Martin.

This song was a first-rate example of their partnership, in which a premium was placed on melodies and vocals delivered with pin-point precision. This track should be prescribed listening for any pop songwriting masterclass.

4. ‘Lucky’ (2000)

Once again, Britney counteracted the raised eyebrows caused by the slightly racy Oops!... I Did It Again with a refined power ballad. Interestingly, the lyrics detail "a Hollywood girl" who is "lost in an image, in a dream".

Did Britney already begin to feel the corrosive nature of the music business only two years into her career?

5. 'I'm a Slave 4 U' (2001)

With this heady single, Britney decidedly moved away from the bubblegum pop of her first two albums for a more adult sound. This means harmonies were jettisoned for heaving beats and sweet vocals made way for more sultry and panting sounds.

As well as being a global hit, the track was responsible for one of the great VMA Awards performances, where Britney took to the stage in 2004 draped with a white python.

6. 'I'm Not a Girl, Not Yet a Woman' (2002)

With a title that can also be used to sum up the thin line Britney has skirted throughout her career, this decent ballad has the singer really focusing on the emotional turmoil that comes with transitioning to adulthood.

Being a grown-up is not just about big night outs, as in the preceding single I'm a Slave for 4 U, but also being more circumspect and independent. "There is no need to protect me," she sings. "It's time that I learn to face up to this on my own."

7. ‘Toxic’ (2004)

The best of Britney's clubby tracks, Toxic is an absolute banger with an east-meets-west production that melds bhangra drums and Bollywood strings with darting synth and surf guitars. Capped off by Britney's arresting and slinky vocals, it went on to land the star her first Grammy in 2004 for Best Dance Recording.

8. ‘Piece of Me’ (2007)

If you are a lifelong Britney fan, anything from 2007's Black Out album will be hard to listen to. Not because of its quality, which was strong enough, but because it was recorded during a period where Britney was at her lowest ebb.

Amid a well-publicised string of increasingly erratic behaviours, the fact she was able to produce decent material was a miracle in itself.

Piece of Me is sturdy dance number powered by squelchy electro synth riffs. The track also finds a defiant Britney taking aim at her media critics.

“I'm Miss American Dream, since I was 17,” she says in the opening verse. “Don't matter if I step on the scene, or sneak away to the Philippines. They're still going to put pictures of [me] in the magazine.”

9. ‘Perfume’ (2013)

It’s good to see Britney sing again with feeling. After four albums full of dark, claustrophobic and, at times, angry club tracks, Britney delivers a more optimistic turn in this late career highlight.

Sure, the synths and EDM beats are here, but they don’t dominate and allows Britney to deliver her most heartfelt vocal performance in years.

10. ‘Matches’ (2020)

With her latest track, Britney reminds us of her carefree sounds of old. Matches recalls her early collaborations with producer Martin and the result is an exuberant piece of pop music.

The fact that the track features the Backstreet Boys gives it an extra level of pathos. Both artists came up together and suffered their own share of public setbacks. This makes Matches more than breezy pop song, but a statement of survival.