30. Hold It Against Me (2011)
Spears previously flirted with dubstep on 2007’s Blackout, but it was Hold It Against Me that dragged the then-underground dance music into the mainstream. A decade later, and its blistering amalgamation of industrial EDM and saccharine pop melodies still feels every bit as audacious and innovative.
29. Radar (2007)
Included on the Blackout and Circus albums due to a contractual obligation that meant it had to be a single, Radar has taken on meme status among Spears fans. But this slinky electro-pop confection has charm to it, Spears’ voice pushed to almost chipmunk levels of artificiality.
28. Till the World Ends (2011)
Spears’ seventh album Femme Fatale, co-executive produced by her old pal Max Martin, led the charge as Eurodance-inspired pop crashed into the charts. But Spears, now a dancefloor veteran, added a bit of spice to what was an otherwise generic era of pop, a prime example being this euphoric yet apocalyptic banger.
27. Me Against the Music (feat Madonna) (2003)
After snogging at the 2003 MTV VMAs, a Madonna and Britney collaboration was inevitable. Whether it would be any good was less certain. But Me Against the Music, with its clackity beats and busy acoustic guitar, is a strange but intoxicating slice of frenetic dance pop that’s more than worthy of its headliners’ star power.
26. Quicksand (2008)
Criminally relegated to a bonus track from Spears’ sixth album, Circus, this grief-stricken song, written by Lady Gaga about the end of a relationship, is a prime example of the sort of melancholic sonic sandpit Spears should play around in more.
25. Make Me (feat G-Eazy) (2016)
After releasing a few duds, a lot was riding on the quality of Spears’ ninth album Glory. It more than delivered, though, with lead single Make Me exemplifying the place she landed artistically. Built around luxuriant, pillowy synths and warm electric guitars, Spears sounds the most engaged and relaxed she has in years. Just don’t mention the horrible G-Eazy rap.
24. Get Naked (I Got a Plan) (2007)
While there are more groundbreaking moments on Spears’ fifth album Blackout (Freakshow incorporated dubstep even earlier than Hold It Against Me), this song best demonstrates the lubricious darkness of the album, Danja’s demonic chanting and deranged synths coalescing with Spears’ come-to-bed vocals into something monstrous and thrilling.
23. 3 (2009)
Recorded specifically for Spears’ second greatest hits album, The Singles Collection, this ridiculously sexed-up oddity about indulging in a menage a trois is so sugary it’ll rot your teeth and the only song about threesomes to make reference to American folk group Peter, Paul and Mary.
22. Lucky (2000)
There are a number of songs that pepper Spears’ discography that are eerily prophetic. Her cover of My Prerogative is one notable example, as is Lucky. Dressed up as a sparkly early 00s take on doo-wop, it’s a disturbing yet syrupy rumination on the bitterness of fame that explores how prestige and celebrity obfuscate isolation and fear.
21. Slumber Party (2016)
The last single Spears released before the now infamous “indefinite work hiatus”, Slumber Party is packed full of her signature innuendo and winking come-ons. There are echoes of Drake’s Hotline Bling in the syncopated synths and plush production, which glides around Spears’ hot-and-heavy vocals until an explosion of horns during the song’s final act.
20. And Then We Kiss (Junkie XL remix) (2003)
Initially meant for Spears’ fourth album In the Zone, the original version of this song has never officially been released (it is floating around online). This remix, however, gives this curious and wistful song a cinematic quality; the aquatic beats, Ray of Light-esque guitars and longing strings emphasise the lust in Spears’ voice.
19. Breathe on Me (2003)
This In the Zone album track is the sexiest song in Spears’ discography, a dive into voyeurism and tantric sex complete with pulsating bass, techno-inflected beats and her breathy moans and ASMR-worthy vocal fry. “We don’t need to touch, just breathe,” she whispers at the end of a chorus that’s so steamy it’ll fog your bedroom window.
18. Break the Ice (2007)
Co-written by Keri Hilson and produced by Timbaland protege Danja, who helmed most of Spears’ fifth album Blackout, this explosive slice of futuristic electro-R&B is so confident, Spears can even pull off the lyric: “I’m gonna hit defrost on ya / let’s get it blazing.” One to chant hungover to your microwave meal for one.
17. Unusual You (2008)
Tucked away on her album Circus, Unusual You is an experimental electro-ballad reminiscent of the collaborative work between Imogen Heap and Guy Sigsworth. Producers Bloodshy & Avant manage to pull out the insecurities and delicacy in her voice, while maintaining the singer’s post-2007 penchant for robotics, resulting in something that’s haunting and surprisingly tender.
16. Work Bitch (2013)
“Go call the po-lice / go call the governuh,” Spears barks in a bizarre LA-cockney-Chelsea accent on this relentless EDM ridicu-banger, taken from her poorly received eighth album Britney Jean. It’s either a satiric glorification of capitalist society or a consumerist fever dream: either way, when Spears demands “you better work, bitch”, it’s hard not to obey.
15. Womanizer (2008)
Dubbed the “comeback” by those around Spears following a chaotic and troublesome time in her life, Womanizer feels engineered to be a hit. Built around an insanely repetitive hook (“Womanizer, woman-womanizer, you’re a womanizer …”), it’s a slick, almost annoyingly catchy wallop of the kind of dance-pop that Spears has mastered.
14. How I Roll (2011)
There are experimental curios on almost every Spears album, but the rubbery elasticity of How I Roll from Femme Fatale is by far the most interesting. Singsong, pitch-shifted melodies are paired with Bloodyshy & Avant’s glitching and effervescent production, all of which feels very proto-PC Music.
13. Man on the Moon (2016)
Recalling the hurt that often lurks beneath the joviality of Lesley “It’s My Party” Gore’s work, this whimsical yet melancholic album track from Glory obscures its aching heart and pangs of loneliness behind jolly marimbas and a twanging electric guitar. Spears’ sadness breaks through, however, as she sighs: “I can’t compete with the stars in the sky / I’m invisible.”
12. (You Drive Me) Crazy (The Stop! remix) (1999)
Following up … Baby One More Time likely required the kitchen sink approach, which is why this is as bombastic as it is. Complete with cowbells, industrial beats, turn-of-the-millennium orchestral stabs, a huge anthemic chorus and Spears purring like her life depends on it, it’s a gargantuan masterclass in unashamed overindulgence.
11. Born to Make You Happy (1999)
This lovelorn mid-tempo may include some questionable and antiquated lyrics that cross from devotional into subservient, but it also houses one of Spears’ greatest and most vulnerable vocal performances. Lapping, watery production gives everything a wistful and dreamy quality, while hurt and desperation leak from every line she sings, intensifying until the song’s climactic key change.
10. Oops! ... I Did It Again (2000)
“I’m not that innocent,” Spears declares on the chorus of Oops! …, which rips apart the melancholic pining of its older sibling … Baby One More Time and replaces it with a commanding coquettishness. Piston-like percussion and slapped bass only bolster the sound of someone who’s just come into her power as a pop star.
9. Touch of My Hand (2003)
Apparently the first song written for In the Zone, Touch of My Hand really ought to have been a single, although the song’s themes of sexual self-pleasure would have never made it on to the radio in George W Bush’s United States. Nevertheless, this is one of Spears’ most sensual and introspective songs, and one of the better odes to masturbation in pop.
8. Everytime (2003)
Spears is no master balladeer, although Everytime is the exception. A sparse and delicate lullaby, it’s a rare moment of crushing vulnerability for the Princess of Pop that traces the devastation of heartbreak and the quest for absolution from past mistakes. There’s no tidy resolution, just Spears desperately seeking forgiveness.
7. Gimme More (2007)
“It’s Britney, bitch!” is one of the most brilliant opening lines in the history of pop music taken from one of the 21st century’s defining records, Spears’ fifth album Blackout. Crunchy and hypnotic, Gimme More is a bleary-eyed stomper that brings to mind stripper poles and sticky club floors. When Spears utters: “I just can’t control myself,” you absolutely believe her.
6. I’m a Slave 4 U (2001)
Spears’s maturation from bubblegum pop star to grownup sexpot was aided by the Neptunes, who provided the sweaty and sensory production on I’m a Slave 4 U. Dissonant and exotic synths converge with Spears’ charged whispered vocals, which are pushed in the mix to feel as if she’s sultrily groaning right into your ear.
5. Overprotected (2001)
“My life has been so overprotected,” Spears laments on this oddly prescient Max Martin-produced marvel, her voice bristling with frustration and weariness. Pulling in all the sonic punches from previous hits (funky guitars, orchestral hits and stacked chord progressions) and more hooks than seemingly possible, it’s an epic coda to her initial partnership with Martin, with whom she wouldn’t collaborate again for nearly a decade.
4. Toxic (2003)
The moment that Bollywood string sample kicks in, Toxic grips you by the neck and drags you along for one wickedly weird ride. Spears delivers a vocal that’s razor sharp, full of hard consonants and breathy rasps, while the breakneck pace leaves you so delirious that you barely notice the addition of a surf guitar or the crunchy, metallic breakdown halfway through. This is the sound of Spears at the height of her power.
3. … Baby One More Time (1998)
Spears’ debut single not only made her a superstar but ushered in a new era of pop that would shape the world of music for the next two decades. Along with its instantly recognisable piano riff, her unique vocal delivery is infused with yearning, melodrama and the hot surge of teen hormones. Arguably the best debut single of all time.
2. Piece of Me (2007)
Spears’ songs have often grappled with her relationship to fame, but the exhilarating Piece of Me is the only track to ever go into specifics, albeit with a snarl and a snigger. “I’m Miss American Dream since I was 17,” she spits over crowing synths and metallic beats, her voice so heavily processed it falls into the uncanny valley. A searing takedown of modern celebrity.
1. Stronger (2000)
Any song that begins with a foghorn ought to be applauded. Blistering and prickly, this is Spears at her most confrontational (“Hush just stop, there’s nothing you can do or say,” she sneers), an exhilarating ride-along with someone finally claiming their autonomy. The chugging beats and her vocal yelps are combative, while the middle-eight feels like someone bracing themselves for battle. It’s a pertinent stance when taken in the context of Spears’ life at the moment, but hers is a story of defiance and fortitude. “My loneliness ain’t killing me no more,” she states self-referentially. “I’m stronger than yesterday.”