20 years ago on October 23, 1998, Britney Spears released her first single “… Baby One More Time.”

Since then she’s become a pop superstar, Madonna-snogger, LGBT ally, Vegas showgirl and all-round legend.



To mark the anniversary of her classic debut, here at PinkNews we’ve decided to rank every one of her 42 singles from great to greatest.

42. “From The Bottom Of My Broken Heart” (1999, from …Baby One More Time)

The last single from her debut album, this slowie showed that Britters was about more than bouncepop and dancing in your school uniform. An early indication that she’s always had a better voice than people give her credit for, though Classic Teenpop Balladry isn’t her strongest suit.

41. “Don’t Let Me Be The Last To Know” (2001, from Oops!…I Did It Again)

Britney again used the final single from an album to wind down the tempo and show off her often overlooked vocal range. It’s not that Britney can’t do slow tracks (“Out From Under” and “Unusual You” from Circus are two masterful electroballads), but they don’t always have the energy to push them through. So it is here, despite some additional lyrics written by Shania Twain

40. “Slumber Party” (feat. Tinashe) (2016, from Glory)

Britney sexes things up for this Glory single featuring Tinashe that typifies her ‘10s approach of hitting more markets and Spotify playlists by clocking up the guest stars. A post-Drake saucefest, it’s a slow-motion pillow fight in your pants that veers a little too near snoozy.

39. “Scream & Shout” (with will.i.am) (2012, from #willpower)

will.i.am is in full cynical flow on this dance hit that catapulted Britney to the top of the UK charts. Co-written by Tulisa and released when Britney was on the US X Factor, it very much feels like the box-ticking branding exercise it is. Even a cheeky “Britney, bitch” sample from “Gimme More” can’t force it up our rankings.

38. “Make Me…” (feat. G-Eazy) (2016, from Glory)

Like David Bowie and Madonna, Britney has a habit of jumping on a bandwagon just in time to ride it with style. This slowed down sex jam is right on the zeitgeist and had her move away from her recent dancepop excursions. It’s suitably slinky and sultry but lacks a bit of drive, while the guest rap from G-Eazy comes off more than a little L-Azy.

37. “Criminal” (2011, from Femme Fatale)

Yet another ballad (you can tell we’re getting these out the way a little early), but this time with a twist. A flute! Not Max Martin’s most catchy collaboration with Britney, but an eclectic-if-a-bit-confused fusion of late Madonna and classic ABBA.

36. “Pretty Girls” (with Iggy Azalea) (2015)

Not the most obvious choice of hook-up for mid-’10s Britney and not the most well-received, either. Iggy’s rapping is an acquired taste, but she’s always better when veering in a more poppy direction, which this collaboration definitely allows. Not nearly as bad as its reputation suggests though, and for all its disposability, “Pretty Girls” is actually pretty fun.

35. “Perfume” (2013, from Britney Jean)

Co-written by Sia, this isn’t a track about Brit’s fragrance range. If you’ve not been counting, she’s now released 24 (TWENTY FOUR) perfumes compared to just nine studio albums. Anyway, it’s actually a powerful bit of bitter balladry about making sure your fella’s next (simultaneous?) girl gets your scent all over her (“I’m gonna mark my territory”).

34. “Do Somethin’” (2005, from Greatest Hits: My Prerogative)

A Bloodshy & Avant offcut that ended up as a sweetener and extra single from Britney’s first hits collection. It’s a solid enough slab of dance pop, though it lacks that little bit of something special that distinguishes her very best singles.

33. “Ooh La La” (2013, from Music from and Inspired by The Smurfs 2)

While her own albums were getting increasingly adult, Britney flung out this more out-and-out fun track for a Smurfs movie sequel because hey, why not? A bit retro, a bit poppy, a bit electro, a bit silly and there’s nothing wrong with that.

32. “If U Seek Amy” (2009, from Circus)

A Kotecha/Martin/Shellback number and maybe the daftest song in Britney’s whole discography. We get what she’s trying to do, but really “All the boys and all the girls are begging to If U Seek Amy” is barely a single entendre. Still lots of robotic pop fun to be had, though.

31. “Sometimes” (1999, from …Baby One More Time)

A grown-up teenpop song from her first album, “Sometimes” was one of those early Britney singles that hinted at her having a longer career than the flash-in-a-pan predictions. One of her more adult (but not adult) tracks that drips with ‘90s singer-songwritery charm.

30. “I Wanna Go” (2011, from Femme Fatale)

Savan Kotecha pitches in again on some songwriting to help out usual Britney backers Martin/Shellback for a straightforward, slightly anonymous bit of auto-tuned dancepop that doesn’t try to break any rules but instead shows that Spears is still more than capable of hanging at the club with anyone.

29. “3” (2009, from The Singles Collection)

In which Britney basically bangs on about how brilliant MMF threesomes are for three minutes and thirty-three seconds (“One, two, three / Not only you and me / Got one eighty degrees / And I’m caught in between”). What’s not to like? Released to trail her second best-of, it did the trick of grabbing a bit of attention for the collection.

28. “Lucky” (2000, from Oops!…I Did It Again)

“This is a story about a girl named Lucky.” And no, it’s not a revenge tale from an angry teen who hunts down her cruel parents, but actually a ‘60s-infused self-reflective bit of pop. “She’s so lucky, she’s a star / But she cry, cry, cries in her lonely heart.” Despite the retro sheen, there’s a real sense of genuine emotion Spears gets across with some neat vocal flourishes.

27. “Outrageous” (2003, from In The Zone)

Written and produced by R. Kelly, but we’ll skate over that, shall we? It was also scrapped from Halle Berry’s flop Catwoman and never got a proper music video after Britney busted her left knee after shooting early scenes with Snoop Dogg (there’s a 45-second edit fans have extended to a full-length clip). Despite that, the song survives as a funked-up, off-beat visit to the (sex) club.

26. “Hold It Against Me” (2011, from Femme Fatale)

A double entendre so old and cheap it’d make your skin crawl if anyone else in the world used it (“If I said I want your body now / Would you hold it against me?”), somehow Britney gets away with it. The utterly filthy dubstep breakdown certainly doesn’t hurt. The line actually came from co-writer Bonnie McKee talking about Katy Perry, who was originally in line for the song before Dr Luke and Max Martin decided it’d fit Britney better

25. “S&M Remix” (with Rihanna) (2011, original version on Loud)

Ester Dean’s hit for Rihanna got a pop makeover when Britney added her vocals for this remix. A total smash, and not just for that sexed-up duet at the 2011 Billboard Music Awards with bodysuits, PVC, masks, poles and handcuffs. It’s not exactly subtle, but few do balls-out sexpop at the club better than Rihanna, and Britney completely holds her own.

24. “I Love Rock ‘N’ Roll” (2002, from Britney)

Originally by Alan Merril, the version everyone knows best is by Joan Jett & The Blackhearts. Britney’s character performed it karaoke style for her movie Crossroads and she got in the studio and did it properly, too. Not as heavy rockin’ as Joan, and not as funky or revamped as it could’ve been either, but it’s still a pretty solid take.

24. “My Prerogative” (2004, from Greatest Hits: My Prerogative)

A cover of Bobby Brown’s ‘80s New Jack hit, “My Prerogative” led Britney’s first singles compilation and lent it its name. Bloodshy & Avant’s sharp production give the song a perfect modern pop sheen without losing any of the funk, groove or swagger of the original.

22. “Me Against The Music” (feat. Madonna) (2003, from In The Zone)

The Queen of Pop passes on the baton to the Young Pretender. While it’s not the greatest single by either pop icon, it’s still remarkable that egos were put aside for this to happen. Remembered more for their cross-generational MTV VMAs girl-on-girl snog, this single has survived the outrage and actually grown in stature over the years.

21. “I’m Not A Girl, Not Yet A Woman” (2002, from Britney)

Dido joined forces with the Max Martin/Rami hit factory and you can hear her AOR vibe all over this soaring bit of balladry. Originally meant for a standalone Crossroads soundtrack, Britney decided to keep it for herself when that project fell through. Sure, it’s a bit wet and safe, but a standout vocal performance and Britney’s real connection with the lyrics elevates this.

20. “Someday (I Will Understand)” (2005, from Britney & Kevin: Chaotic)

Britney’s forgotten single, and unfairly so. Taken from her (also forgotten) reality TV show Britney & Kevin: Chaotic which charted her (almost forgotten) marriage to Kevin Federline. A rare track written by Britney herself and with classy production by Guy Sigsworth, it’s one of the most genuine, heartfelt and emotional performances of her career, and deserves a wider audience.

19. “Circus” (2008, from Circus)

A fresh, sparky, glitchy and hook-laden swagger of energy that underlined Britney’s total return to form towards the end of the last decade. “Well baby I’m a put-on-a-show kinda girl/ Don’t like the backseat, gotta be first” she zips, foreshadowing her gamechanging Vegas residency a few years in advance.

18. “Overprotected” (2001, from Britney)

On her third album Britney was breaking out of the parental and pop straightjacket of her earlier years. While “I’m Not A Girl…” had her between worlds, tentatively stepping out on her own, this track is a much more funked up, independent burst. Yeah, she’ll make mistakes, but they’ll be hers (“I’m so fed up with people telling me to be / Someone else but me”).

17. “Work B**ch” (2013, from Britney Jean)

After ‘Scream & Shout’ we wouldn’t have opted for another will.i.am hookup, but that’s why we don’t make the decisions. “Work B**ch” is one of the most brilliantly aggressive, powerful, strutting and heavy tracks in Britney’s back catalogue, underpinned by some banging beats from Swedish House Mafia’s Sebastian Ingrosso. An absolute monster of a club hit.

16. “(You Drive Me) Crazy” (1999, from …Baby One More Time)

Anyone in summer 1999 thinking Britney was a one-and-a-half hit wonder would have been disabused of that notion when “… Crazy” hit radios. Don’t mind the squalling guitars, this is another perfect bit of ‘90s pop. Very nearly as catchy as her debut, it’s got the same self-assured swagger that would make Britney a breakout star.

15. “Break the Ice” (2008, from Blackout)

Danja, Jim Beanz, Keri Hilson and Marcella Araica join forces for this genre-bending slab of crunking rave robopop, but it’s all held together by a cracking performance by Britney herself. No, really. Cut-n-paste, heavy-treated vocals will never get the respect of octave-spanning warbling, but it’s hard work to make things sound this easy.

14. “Tom’s Diner” (with Giorgio Moroder) (2015, from Déjà Vu)

While Suzanne Vega’s ‘80s original didn’t get a massive audience, everyone remembers DNA’s acid remix that scaled the charts in 1990. Electronic music icon Giorgio Moroder enlisted Britney to do Suzanne’s bit on his take, and although it’s a bit more obvious than DNA’s subtle masterpiece, it still shimmers and shines with disco class.

13. “Born To Make You Happy” (1999, from …Baby One More Time)

A break-up song often unfairly dismissed as regressive and misogynistic. On the surface the lyrics are more than a little limp and pathetic (“I don’t know how to live without your love / I was born to make you happy”), but this is a break-up song. It’s about capturing that pain, denial, and self-pitying misery right after things go south. And the powerful pop backing and unbreaking vocals show that Britney will more than live to fight (and love) another day.

12. “Boys (Co-Ed Remix)” (2002, from Austin Powers in Goldmember: Music from the Motion Picture. Original version on Britney)

From when The Neptunes and N*E*R*D (and specifically Pharell) were everywhere, but long before they were EVERYWHERE. Britney catches the wave before it breaks and hooks up with the boys for “Boys” and one of her most sleek and sharp pop hits. The single remix adds an effortlessly cool Pharrell rap that takes it to the next level.

11. “Womanizer” (2008, from Circus)

Despite her personal difficulties around Blackout the album itself rightly put Britney back on top of the pop world, and she quickly built on that by rushing straight into its follow-up Circus. Songs like “Womanizer” show why it was much more than Blackout II, with its glitchy beats, aggressive loops and harsh synthesiser making it one of Britney’s strangest-yet-hookiest tracks.

10. “Toxic” (2004, from In The Zone)

Cathy Dennis (who wrote Kylie’s “Can’t Get You Out Of My Head”) joining forces with Bloodshy & Avant has H I T written all over it and “Toxic” absolutely delivers. Kylie actually turned it down, and to be honest we can’t imagine her doing a better job than Britney. One of Brit’s most enduring and ubiquitous singles, the catchiness belies the quirky fusion of a Bollywood hook and hip-pop vibes.

9. “I’m A Slave 4 U” (2001, from Britney)

The lead single from Britney made a massive statement. The Prince-esque title hints at its sex and funk fusion, but the lyrics aren’t as submissive as a first glance suggests. Britney is a slave to the club as much as she is the guy, and the lyrics big up ‘talking’ and ‘dancing’ rather than… all that other stuff.

Yeah, it sounds sexy when she says it, but this ain’t Xtina’s “Dirrty.” While the same album’s “I’m Not A Girl…” and “Overprotected” found her on the cusp of striking out on her own, this Neptunes collab showed she was already there.

8. “Stronger” (2000, from Oops!… I Did It Again)

Another Britney break-up song, but absolutely no-one would think this one’s in the least bit pathetic. “I’m not your property as from today, baby,” she sings, and sounds like she absolutely means it, before amazingly inverting the opening words of her biggest hit to date  (“My loneliness ain’t killin’ me no more”). A perfect pop masterpiece.

7. “Till The World Ends” (2011, from Femme Fatale)

After the stocktaking of her second hits compilation, it wasn’t entirely clear where Britney would go next. “Hold It Against Me” may have tiptoed to the club but this second single (and best track) from Femme Fatale jumped in with both feet. Co-written by Kesha and her team, it’s Britney’s most convincing trance anthem. A party classic.

6. “Everytime” (2004, from In The Zone)

Written as a response to ex-boyfriend Justin Timberlake’s “Cry Me A River,” “Everytime” is often remembered only for its controversial death-in-a-bathtub music video, which is a shame.

Despite some limp efforts scattered around her albums, Britney can actually do some utterly compelling and heartbreaking ballads, and this is her very best. Beautiful, disarming, and emotionally raw.

5. “Oops!…I Did It Again” (2000, from Oops!… I Did It Again)

The lead single and title track from Britney’s second album does what it says on the tin. Another absolutely massive hit that proved that she was going to be around for a long while yet.

It’s three minutes and thirty seconds of sorry-not-sorry swagger and utter pop perfection, capped off by a ridiculous/amazing spoken word bit that makes sure you’ll never watch Titanic in the same way again.

4. “Piece Of Me” (2007, from Blackout)

Bloodshy & Avant and Robyn collaborator Klas Åhlund get together for this J’accuse against the media, industry and fans who were hounding Britney nearly to death around this time.

Pop stars whining about the press (no matter how justified) usually come off terribly, but this thuddering, juddering mess of loops, glitches, hooks and “who me?” snark (“No wonder there’s panic in the industry / I mean please”) is a rare and utterly righteous exception.

3. “Radar” (2009, from Blackout and re-released as a bonus track on Circus)

Inexplicably delayed until the end of the Circus campaign, “Radar” is actually one of the standouts from Blackout (still Britney’s very best album). Less frenetic than its other pair of singles, “Radar” is a more slinky fusion of electro, R&B, disco and pure pop.

For all the credit Kanye got for the innovative use of Auto-Tune as an instrument on 808s & Heartbreak, you could argue that Britney got there a year earlier here with her heavily-treated vocals.

2. “… Baby One More Time” (1999, from “…Baby One More Time”)

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Where it all began, and one of the greatest ever debut singles. It rightly went #1 all over the world and launched the career of a superstar.

A perfect power pop symphony in three and a half minutes, it was apparently turned down by both the Backstreet Boys and TLC before Max Martin and Rami handed it over to Britney. We can’t imagine it any other way.

1. “Gimme More” (2007, from Blackout)

Forget all about that disastrous 2007 MTV Video Music Awards performance, “Gimme More” is the ultimate pop comeback single. In her post-Vegas position as total pop royalty once more, people may not remember that Britney was written off as a busted flush after the K-Fed years.

She was dismissed as a mom whose best years were in her rear-view, or worse still, a career-ending public breakdown away from disaster. But the music never, ever lies, and this is Britney’s most thrilling, career (re)defining, finest moment.

Written by Marcella Araica (aka “The Incredible Lago”), Danja, Jim Beanz and Keri Hilson, their irresistible glitchpop production is capped off by a career-best performance from The Legendary Ms Britney Spears.

Oh, and Britney laid down the vocals on Blackout when she was SEVEN MONTHS pregnant, and finished them off less than a month after the birth of her second kid. An Absolute Queen.




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