One of the most fascinating entertainers of our time, Britney Spears has defined what it means to be a pop star. That’s why Billboard recently named Spears – who turned 43 on December 2 – as the sixth greatest pop star of the 21st century, just behind the likes of Beyoncé, Taylor Swift and Drake.
With a best-selling memoir, a headline-making Instagram presence and an upcoming biopic directed by Wicked’s Jon M Chu keeping her busy, music clearly isn’t a priority in Spears’ life right now. In 2022, she vowed to never perform live again after her highly-publicised conservatorship had left her “traumatised”.
Despite this, Spears will always remain a widely beloved pop icon. Case in point: 2024’s three musketeers of pop: Charli XCX, Sabrina Carpenter and Chappell Roan, all cite her as a major influence. And you only have to glance at social media during Halloween before an air hostess, bikini-clad snake charmer or pig-tailed schoolgirl pop-up on your feed.
Here’s our pick of her best songs.
10. My Prerogative (2004)
Listen, we know Spears’ covers (which include The Rolling Stones’ (I Can’t Get No) Satisfaction and Joan Jett & the Blackhearts’ I Love Rock ‘n’ Roll) haven’t always gone down well. Jett herself said she was left “confused” by Spears’ 2001 cover, and Bobby Brown publicly wasn’t a fan when she sank her teeth into his new jack swing classic for her greatest hits album three years later. But retrospectively, Spears’ Arabic-tinged synthpop take of My Prerogative – which still sounds fresh 20 years later – was the first time she responded to the media speculation surrounding her personal life, a theme she would continue later in her career. And we all know Britney’s at her best when she’s hitting back.
9. Lucky (2000)
Often overshadowed by its album siblings Oops… I Did It Again and post-conservatorship anthem Stronger, Lucky – which was released at the pinnacle of Spears’ fame – lyrically foreshadows the singer’s struggles with fame and personal freedom. But juxtaposing its haunting storyline is the song’s fizzy, almost fairytale-esque package of bubblegum pop production. The way Lucky appealed to Spears’ then-tween fanbase, gave us a glimpse into a universe where Spears is an Oscar winner and predicted her later struggles means it’s well-deserving of a place in the Hall of Fame of her career.
8. I’m A Slave 4 U (2001)
It’s unsurprising that I’m A Slave 4 U, one of Spears’ signature songs, was actually a Janet Jackson reject. Everything from her breathy, sultry vocal delivery, intricate choreography and Pharrell-backed R&B production marked a transition in a then 19-year-old Spears’ career, where she shed her girl-next-door persona to find her feet as a young woman, later inspiring Christina Aguilera, Miley Cyrus and Selena Gomez to do the same. Plus, I’m A Slave 4 U birthed one of the shining moments of Spears’ performance catalogue, where she danced around the stage of the 2001 MTV Video Music Awards with a yellow python draped around her shoulders. The definition of iconic.
7. Everytime (2003)
Spears has often faced criticism for relying on songwriters to craft her hits, but she proved her naysayers wrong with 2003’s Everytime. Believed to be a response to ex-boyfriend Justin Timberlake’s scathing Cry Me A River, the evocative ballad – which Spears co-wrote and composed herself - remains her best, and is one of the only points in her discography where the upbeat, dancy nature of her music takes a backseat for something more fragile and vulnerable, showing off her falsetto in the process.
6. Gimme More (2007)
So, 2007 was not a great year to be Britney Spears. But amid the media-aggravated storm of her personal life, her magnum opus, Blackout, was born. The album was inducted into the Rock & Roll Hall Of Fame for its influence on modern pop music in 2012, and its dark dancefloor allure is no better characterised than by its lead single, Gimme More. The track’s thumping production sounds straight out of a strip club (which is where the song’s music video is set), and its suggestive nature is only bolstered by Spears’ repeated demands for “more”. The icing on the cake? The song’s off-the-cuff spoken intro, which created one of pop’s most memorable catchprases: ‘It’s Britney, bitch.’
5. …Baby One More Time (1998)
Most of what there is to be said about Spears’ debut single and biggest hit has already been said: it ushered in an era of bubblegum teen pop in Western music, became one of the best-selling songs of all time and catapulted a 16-year-old schoolgirl into an everlasting pop phenomenon. With its cultural significance, it’s hard to picture the hit as initially intended: a track for the Backstreet Boys, then TLC, and even British boyband 5ive – all of whom rejected it. Alongside Thriller and Vogue, its music video is one of the most famous of all time – and Spears herself was the mastermind behind it, swapping out director Nigel Dick’s cartoon for the schoolgirl idea.
4. Breathe On Me (2003)
Few outside of Britney’s regular listeners know about Breathe On Me, which is a shame, because the song, in all its hypnotic, trip-hop glory, is a bonafide pop masterpiece. Appearing on the stacked tracklisting of 2003’s In The Zone alongside mammoth hits like Toxic, Everytime and Madonna link-up Me Against The Music, you’d think Breathe On Me would be forgotten. But thanks to its throbbing euro-trance bassline and Spears’ overt demands during a quest for sexual pleasure, it remains a highlight of her catalogue.
3. Toxic (2003)
Unlike …Baby One More Time, it feels like the magic behind Toxic can never be talked about enough. A result of chopping the soundtrack of a 1981 Bollywood film and combining it with a warped surf guitar, futuristic electro-pop beat and Cathy Dennis’ songwriting genius, Toxic is pure pop gold. Its standing in the league of pop fame is elevated by Spears’ breathy vocal delivery and the song’s famed secret-agent style music video, the vision for which Spears sketched out herself and handed to the video’s director, complete with details of her nude diamond get-up and the scene where her air hostess character playfully wipes a spilt drink from the crotch of a male passenger.
2. Break The Ice (2007)
Despite receiving little promotion at the time aside from an anime-style music video, Break The Ice is one of Spears’ most underrated – and best – songs. Written by Keri Hilson and produced by Timbaland protégé Danja, Spears’ airy voice finds its element in a storm of electro-tinged R&B, crunk and choir backing vocals, and it’s without a doubt home to one of her most confident vocal deliveries. Like most of Blackout, it’s cold hard dance music that feels timeless – and serves as a reminder of the often unsung magic of Spears’ voice.
1. Piece Of Me (2007)
Where My Prerogative was a thinly veiled call-out to the press, Piece Of Me was a straight-up middle finger. Enlisting Toxic producers Bloodshy and Avant, Spears uses sleazy electropop as her weapon of choice on the diss track, which sees her rebuff the scrutiny piled on her at the time concerning her parenting abilities, relationships, weight and endless paparazzi drama. If things couldn’t get better, Britney’s gloriously autotuned vocals – which instead of trying to mask any imperfections actually boost the no-fucks-given energy of the song – are supported by background vocals courtesy of Robyn. Piece Of Me isn’t just a dance-pop classic: it was a rare glimpse into the whirlwind life of one of the world’s most famous entertainers.
