It’s Britney, bitch.

Baby One More Time (1998)

If you weren’t somewhere in your teens in the late 90s you can’t even begin to understand the actual global impact this song, and by extension, the arrival of Spears onto the music scene, truly had. Moreover, the sound, a refinement of the syncopated Swedish pop that legendary producer Max Martin had begun developing under the Cheiron Studios banner in Stockholm, was something we’d never heard before (see - Ace of Base, All That She Wants, The Sign, the progenitors for this type of audio production.) Minimalistic synthetic beats, piano riffs, deep funk guitar bass lines and glistening high end effects. 

Couple this with the fact that the entire world went into a nosedive over the sexualisation of a (then) 15 year old female performing eroticised choreography in a school uniform (though the creative concept was her idea and the initial treatment for the video was scrapped at her insistence) and Spears’ arrival was utterly volcanic. Add to that the David LaChapelle Rolling Stone cover shot in 1999 where a 16 year old Spears was seen in her underwear cuddling a Teletubbie toy, cue more uncomfortable conversations. The launch of Spears’ career was so far over the line of acceptability by any standard that it’s kind of mindblowing that it ever happened and with hindsight set the tone for the sinister exploitation that was to come.

Director - Nigel Dick

(You Drive Me) Crazy (1999)

The first song title of many that reads differently with hindsight, Crazy was a pre-Y2K smash for Spears that followed on from the more low key ballad Sometimes and saw her doubling down on high energy dance pop and cementing her signature Southern drawl “aowwwwww” vocal device.  The scale of the set, the transformation from small town Diner worker into warehouse party starter, the sheer number of extras, the Walmart x Mickey Mouse Club style wardrobing that would become a signature across her promos and the first real outing for the crimped blonde hair look that would become as synonymous with her image as the high pony is for Ariana. There was an aggression and an edge to her performance and lipsync that hinted she had more to her than just a cutesy and vulnerable innocent teenager. Oh, and Melissa Joan Hart was in the video. Something to do with a movie tie in.

Director - Nigel Dick

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

The one set on Mars. The one with the Titanic reference (“but I thought the old lady dropped it into the ocean in the end?”).. The one where unknown extra 2 in mission control literally says “Cute, what is it?” in response to unknown extra 1 finding the album cover image of Spears on the surface of the red planet and unknown extra 1 replies “Oh, it’s cute alright”. It’s. About the artist whose song the video is for.

Let’s just let that sit there for a minute.

“It’s.”

“It” was the biggest artist in the world. Rage aside, if the grand council of the Gay Agenda ever decides to enact a membership ritual in order to qualify for the conceptual gay badge, knowing the choreography for this video will be a basic requirement. Heck, it even made it into a scene in Will and Grace. The red PVC (no latex here, no budget for it) jumpsuit, the heart pump, the “not that innocent”, the to-camera performance (fun fact, Spears delivered close up lip-sync shots behind a one way mirror so she could be looking at her own reflection… The artistry…). The sophomore album is often the most tricky, but this absolute banger showed Spears wasn’t just a one album wonder here to FAFO, and the overhead spiderweb god shot became a staple of female pop promos for decades to follow. Controversial, but clearly a more iconic video than Baby One More Time. Deal with it. 

Director - Nigel Dick

Lucky (2000)

Having to exclude Stronger from this list was probably the hardest and most time consuming deliberation of this whole selection process. But on measure, Lucky pips Stronger to the post for the sheer fact of it foreshadowing what was to come later in her career. Containing possibly her greatest lyric, “if there’s nothing missing in her life, then why do these tears come at night?”, Lucky feels positively Shakespearean in its prediction of a tragic downfall. It even starts with Spears walking onto a stage and with a downcast look announcing “This is a story about a girl named Lucky…” like we didn’t all get the Lucky = Britney coding. 

The narrative of Spears watching herself from afar as her likeness succumbs to the soul destruction of vacuous industry praise, superficial adoration and existential loneliness is, quite frankly, the most meta statement on the music business ever smuggled into a seemingly glossy pop video. The one where we realised she had her own agenda. “Best Actress, and the winner is… Lucky.” Surprisingly conceptual, until you learn that Dave Meyers directed it (see - Ariana Grande no tears left to cry, Rihanna Where Have You Been and on and on. Meyers is the OG.)

I’m a Slave 4 U (2001)

Song title number two that sends shivers up the spine. Directed by Francis Lawrence, who, fun fact, went on to helm three of the Hunger Games movies, Slave sees Spears deliver one of her most recognisable pieces of choreo (launching a thousand LA WeHo memes) on a set resembling a Brazilian favela, drenched in sweat, with probably her best ever hair and makeup look. 

The fact that she delivered her key dance performance in one take (or so the legend goes) just speaks to her perfectionism. Yes Gen Z, we get that you stan Tate McRae for her dancing (and, spoiler alert, who knows she might be next year’s Pride focus artist), but this is where it all began. Class dismissed.

I’m Not a Girl (Not Yet a Woman) (2001)

Again, ditching Overprotected (which obviously has a whole meta-narrative we could unpack for an entirely separate essay) was no easy decision. But I’m Not a Girl marked a move towards a more mature and self-aware Spears and felt like a jailbreak from the expectations of her label, Jive / BMG. Is the video as strong as Overprotected? Possibly not. But this one is all about context and lyrics. “I’m not a girl. There is no need to protect me” lands different knowing what was to come, but the deeper, more natural vocal felt like Spears reclaiming her authentic sound after anonymous men in rooms in New York Little Mermaid-ed a 15 year old (including Lou Perlman, later alleged to have been a “sexual predator” to 00’s boy bands including Backstreet Boys and N’Sync), muted her real singing voice, and told to perform with the pitch and intonation of a child if she wanted to get a record deal.

Literally disgusting. 

(Sidenote, when I finally make a film about Spears with her consent and participation it will be called ‘The Little Mermaid’ and Disney can go ahead and sue me and we’ll see how that lands.)

The track accompanied Spears’ first and only film role, Crossroads, a sort of post-feminist road movie which, when you look back on it, was way grittier than you’d expect a Hollywood release with the world’s biggest female artist at the time to be given the Sketchers and Garnier shampoo product placement that likely funded a good deal of the production cost. Fun fact, Dido, who was having a moment in the spotlight in the early noughties, takes credit for additional writing on the track.

Director - Wayne Isham (who did Living on a Prayer for Bon Jovi and a bunch of Metallica vids amongst others.)

Toxic (2004)

What can you say? Spears’ biggest anthem by a royal mile, top five in 15 countries, number one on the Billboard chart, 6 times platinum certified by the RIAA and her only Grammy winning record across the span of her career. Originally offered to (and rejected by) Janet Jackson and Kylie Minogue, Toxic has, to date, earned more than 1bn streams on Spotify, making it her biggest hit and likely most well known song across the generations. The Joseph Khan-directed homage to air travel riffs on a sample from the 1981 Bollywood track Tere Mere Beech Mein, a sting refrain that will forever be stamped into the legacy of humanity’s artistic narrative. And let’s not forget the red wig black leather jumpsuit and diamond nude illusion looks. Serving.

The track had had such a seismic cultural impact that it actually made it into an episode of the BBC’s Dr Who in 2005, where it was used to “bid farewell to the cradle of civilisation” by “mourning her with a traditional ballad”. Cut to Toxic being played as the earth is on the brink of complete obliteration. And, frankly, when WW3 inevitably drops we’re fully onboard with our mutually assured destruction being scored to Spears purring “a guy like you should wear a warning. You’re dangerous, I’m loving it” to Vladimir Putin. 

Also, Tyson Beckford shirtless on a motorbike. So there’s that.

Everytime (2004)

The one where she hinted at the abortion she got in 2000 because Justin Timberlake didn’t want to be a father. 

“I make believe that you are here, it’s the only way that I see clear. What have I done? At night I pray that soon your face will fade away. Please forgive me. This song’s my sorry”.

She wanted to keep the baby… That revelation happened in a “pop” song.

Take a moment.

Director - David LaChapelle

Honorable mention - Me Against the Music (2003). The one with Madonna that sparked a French and Saunders spoof.

Gimme More (2007)

It’s 2007, you’re in the middle of an acrimonious custody battle over your two children, you’re being coerced into taking permanently brain damaging doses of lithium with the threat of being declared an unfit mother, you’re going through addiction issues, you’re two divorces deep, the press has turned on you, you’re about to shave all your hair off to avoid a follicular drug test, you’ve had an IUD implanted against your will and a year from now you’ll have a complete mental breakdown and lock yourself in a bathroom with your children before emergency services are called and you’re sectioned and stretchered off to a medical facility while helicopters circle above, paparazzi shoot you through the ambulance windows without the police intervening and the world looks on without an ounce sympathy before your sadistic father executes a bogus legal conservatorship and you’re forced into performing as a glorified slave for a decade until finally, one day, you have enough and tell the world to go fuck itself by walking out of a global press event in Vegas and announcing you’re never releasing music or performing again. Yes, this all happened. This was mass culture. Think about that. And she survived. So yeh, that’s why the gays will be loyal to her until the end, in case you’re wondering.

And so we get to Gimme More from the album Blackout, indisputably Spears’ greatest musical achievement and most powerful statement as an artist . The song received its debut at the 2007 MTV music awards, a performance that should have set red flags waving but instead triggered global derision. 

“They want more? Well, I'll give them more.”

And she did, until it broke her.

Director - Jake Sarfaty

Piece of Me (2007)

This was Britney in zero fucks left to give mode. The video opens on a shot of rabid, cannibalistic paparazzi framed like baying animals in a zoo pen before introducing a group of Britney look-alikes that represent the various fictitious versions of her image, monetized by an insatiable media machine and splashed across dollar store gossip magazines for profit. This wasn’t “just” pop. This was an anti-establishment statement. A massive middle finger up fuck you to the entire Hollywood entertainment industry, and the real beginning of Britney sneaking subversive cultural critique into her lyrics and videos that would culminate in (spoiler alert) 2013’s postmodern anthem, Work Bitch.

Is she singing “you want a piece of me” or “you want a piece of meat”?  Either way, the message is clear, and her calling out the misogyny, body shaming and hypocrisy of the media was a moment that reinvigorated 2000s feminism and still reverberates today. 

“Don’t matter if I step on the scene or sneak away to the Philippines, they’re still going to put pictures of my derriere in their magazines.”

Director - Wayne Isham

Womanizer (2008)

Touted by music ‘journalists’ as her “comeback” album as though Blackout had completely fallen off their radar, 2008’s release Circus served a more narrowly pop-focussed and less confrontational lineup of songs. The true impact of launch track Womanizer can only really be summed up by this clip from drag royalty, Trixie Mattel. “You know why gay people are fast walkers? We’re all singing Womanizer, all day, in our heads.” 100% true and accurate.

Director - Joseph Khan

Circus (2008)

Opening with two gloriously unsubtle product placement shots (one for her own fragrance, one for Bulgari), Circus sees Britney deliver another truthbomb opening lyric - “There’s only two types of people in the world. The ones that entertain, and the ones that observe.”

Somewhere around this era you could tell the spark was gone though, she wasn’t in the moment with the choreo, the styling wasn’t doing what it needed to. It just felt like she wasn’t having fun anymore. The edits get choppier as she stops delivering full sequence dance routines. And that’s when we really knew something was up. The cognitive dissonance was on full show during her Good Morning America first live performance of the track where she seemed detuned and dialled in. And who can blame her?

“Spotlight on me and I’m ready to break.”

Director - Francis Lawrence

Hold It Against Me (2011)

This gets included solely for the weird AF “post production” (if you can call it that) meme sparked by the psychotic lip retouch shot at 1:45 that birthed literal Reddit threads of theories.

Director - Jonas Akerlund (who spoke about the video ten years after the fact here)

Till The World Ends (2011)

After the facial retouch travesty of the previous video, the big takeout from Till The World Ends was a new style of visual treatment that would bleed through into the final Glory era videos, a new surface polish that set the mark for a reimagined stylistic tone (read - beauty retouch settings in Avid).

Finally a song that saw Spears getting airtime in clubs again. The four on the floor beat, the morphy synth melody and the offset bass line made for prime XXL fodder right round this time and if you’re too old to know what XXL in London was then good for you, you’ll need moisturiser one day like the rest of us.

The cyberpunk sister to the Mad Max-ery of Slave 4 U.

Director - Ray Kay

Notable mention - I Wanna Go (2011). Just watch it. VW and Canon product placement. A sick beat. And some sort of daydream narrative that starts with Spears flipping off a press conference and involves Terminator 2 style cyborgs and a dude called Guillermo. No, none of it makes sense but at least she seems to be vibing it. Oh, and the easter egg reference to Crossroads 2 - Cross Harder was a great IYKYK.

Work Bitch (2013)

And so, at last, we get to this one, with lyrics that could literally be a series of lines screamed at her by her father. The British accent caused a commotion, the Beats by Dre fetish ball gag was a thing, the whip work happened, the sharks… No, none of it made sense but this was a fkn bop and she is utterly flawless in every single frame. And the self-referential Planet Hollywood residence reference was, in fairness, marketing genius.

Director - Ben Mor

Perfume (2013)

Written by Sia, whose version of the track is undeniably superior, Perfume is a heartbreaking ode to a broken relationship where one partner knows the other is cheating on them but can’t bring themselves to confront the dysfunction and so we hear the echoes of their insecurity reverberate over a melody that’s utterly tragic. Britney back in acting mode. See - Criminal (2011).

Director - Joseph Khan (and it shows. Pure polish.)

Make Me (2016)

And so we reach the final era and what will likely be Britney’s last ever album, Glory (still in denial about this tbh). Make Me was the launch track from a lineup of sumptuous pop bangers that ricocheted from the schizophrenic doo-wop hard house mashup of Clumsy to the underground bass throbs of Do You Wanna Come Over?

This treat from David LaChapelle sadly never saw the light of day as the official video, and the sanitised American Idol-esque audition video that did eventually take its place just wasn’t the moment.

Slumber Party (2016)

Which takes us to Britney’s last, and possibly final ever, music video for Slumber Party. Spears looks immaculate, and the shot of her crawling across the table towards future and now ex husband Sam Ashgari was just the chef's kiss. Fittingly, it resolves with a set of heavy black drapes closing and the sound of a lock clicking into place. The End.