Best Pop Singers of 21st Century (No. 6)

With the first quarter of the 21st century coming to a close, Billboard is spending the next few months counting down our staff picks for the 25 greatest pop stars of the last 25 years. You can see the stars who have made our list so far here — and now, we examine the century in Britney Spears, a pop force whose dominance over Millennial culture earned her the title as Princess of Pop for her signature vocal tone, hit catalog and show-stopping performances. (Hear more discussion of Britney Spears and explanation of her list ranking on our Greatest Pop Stars podcast tomorrow (Oct. 30).)

Few came, saw, and conquered global superstardom quite like Britney Spears. At the turn of the millennium, the teen queen captured the hearts of millions with her pop hits — and, unknowingly, set a business model that would carry for decades to come. But even when record labels tried to replicate the magic, they fell short, because it was largely Spears incorporating her creativity and personality into her career that made the Mississippi-born talent such a unique force. As the calendar changed centuries, no one held a tighter grip on pop’s new golden age than Britney, who became an icon with a reliable talent for creating zeitgeist-y moments — years before social media even existed. 

While Spears’ celebrity and artistry recalled pop juggernauts Madonna and Janet Jackson, she was more reserved in relation to the limelight and never fully leaned into her fierce cultural impact. While some of her predecessors purposely aimed to bust down societal doors, Spears just wanted to excel as a pop star. She led with Southern charm and understated humility, and that juxtaposition added something special to her star power as it ascended (and sometimes tumbled) through the 2000s and into the 2010s, remaining squarely in the public consciousness to this day.

Ironically, there was once a time when Spears’ endurance was up for debate, with comparisons to flash-in-the-pan pop stars of yesteryear. But really, we should’ve known from her first single that she was here to stay. The release of her debut single “…Baby One More Time” in late 1998 marked a cultural reset, jump-starting a reign that enthralled fans, initially shocked parents and forced the industry to follow her lead. With Swedish producer Max Martin at the helm, the song reached No. 1 on the Billboard Hot 100 — due, of course, in no small part to the accompanying high school-set music video (which, to the singer’s credit, was all her idea, coming after she rejected a video treatment that was much more convoluted). 

At just 16, it was a long time coming for Spears, whose experience and professionalism spanned pageants, gymnastics and a stint on Disney’s All-New Mickey Mouse Club. For the rest of us, it felt instantaneous, with her accompanying album of the same name dropping months later. Coming on the heels of debuts by the Backstreet Boys and *NSYNC, the LP brought the burgeoning TRL era of pop music to new heights and became the best-selling debut by a female teenage artist, moving over 14 million copies in the United States. With her growing arsenal of polished pop hits, dance-heavy music videos and girl-next-door persona, Spears set the stage for an even bigger splash at the beginning of the 21st century. (Britney’s ‘90s accomplishments were not factored into the Billboard staff’s calculations when determining her ranking on this solely 21st century-based list.) 

Spears’ 2000 sophomore LP Oops!…I Did It Again reunited the star with Max Martin, while bringing in veteran hitmakers Rodney Jerkins and Diane Warren for the “more mature” new effort — an arguable assessment, but the 17-year-old knew how to strike a chord with her fans: After all, she was already on a first-name basis with them. In April 2000, she returned with the ultimate friend zone anthem in the set’s title track, decked out in a cherry red catsuit for the now-iconic music video. Its parent album stormed the Billboard 200 upon its release a month later, selling a staggering 1.319 million copies in its first week — at the time garnering the largest first-week sales ever for an album by a female artist.

If critics dismissed her artistry due to her flashy showmanship and sex appeal, it was that very stage prowess that set her apart. Later that year, she hit the 2000 MTV Video Music Awards to perform a medley of “Oops” and a cover of The Rolling Stones’ “(I Can’t Get No) Satisfaction.” In three minutes, she managed a whole career pivot, tearing off a black suit to reveal a little sparkly ensemble — giving new meaning to being “not that innocent.” The media further vilified her for the performance, but it also set high expectations for what women (and Britney herself) could do in pop music. It was also one of the few windows in her career where she tried to strike a balance between live singing and the athleticism of her choreography as future performances would be mostly lip-synced, with Britney focusing on the physicality of her dancing.

With so much access to celebrity nowadays, it’s hard to fully understand the phenomenon that was Britney Spears at her commercial peak, but she was everywhere — dominating award shows, gracing magazine covers, starring in TV commercials, available for purchase as a Barbie doll and, of course, on the tip of everyone’s tongue. She was the pop princess for a new generation, at once sex-positive but demure, and arm-in-denim-arm with *NSYNC’s Justin Timberlake, the pair making for Y2K music’s ultimate power couple. While she supported her fellow women in pop and minded her business, the teen queen had some people angry, and others excessively inquisitive, a misogyny-laced treatment that would only get its proper reckoning years down the line. From intrusive questions about her virginity to men twice her age discounting her work, she remained mostly posed and polite until her next studio offering: 2001’s Britney.

Spears upped the ante for her third album, stepping to the plate as a young woman who unapologetically owned her sexuality. With a backbone provided by hip-hop superproducers The Neptunes, the set’s slinky lead single, “I’m a Slave 4 U,” served as a radical sonic shift for the star. She was still months away from her 20s, but the transition from teen sensation to adult superstar was met with criticism. Yet the song became another vehicle for her to shine on stage — and at the 2001 VMAs, she draped herself in a seven-foot python and churned out her most unforgettable performance to date. While she played up the role of sex kitten, the accompanying project, which continued her No. 1 streak on the Billboard 200, also captured her exploration of womanhood (“Not a Girl, Not Yet a Woman”), yearned for the normalcy of an average life (“Overprotected”) and channeled her inner Janet Jackson (“Boys”). 

Those follow-up singles failed to make the same impact as her former releases, possibly due to a rumored radio suppression, reportedly demoting the songs from high rotation. But by then, Spears had something else to focus on: her foray into Hollywood with her debut feature film, Crossroads. The coming-of-age story boasted a noteworthy ensemble, including Zoe Saldaña, Taryn Manning and Kim Cattrall, with Shonda Rhimes debuting her first screenplay — but despite Spears’ affable charm translating well to the silver screen, the movie didn’t hit the mark with critics. Simultaneously, her culture-dominating romance with Timberlake came to an end after three years, with the heartthrob reportedly ending the relationship via text message. With their split, the tabloids took sides, as rumors of infidelity spread concerning Spears and their joint choreographer Wade Robson, and Timberlake fueled the flames while launching his own solo career – particularly with his second solo single, the No. 3 Hot 100 smash “Cry Me a River,” which included a Britney lookalike in its video. 

It was clear that Spears needed some time away from the limelight, but before the end of 2002, she called off her planned six-month hiatus and started work on her most liberating album to that point, In the Zone. That set was also preceded by a new wave of headlines, courtesy of another steamy VMA performance – this time finding her lip locking with her idol, Madonna. The lightning-in-a-bottle moment prompted international headlines and downright hysteria: It was actually pretty tame by today’s standards, but those few seconds, complemented by cameras panning to a stone-faced Timberlake, rocked the world. In what could be perceived as the passing of the torch, Spears also recruited Madge for the frisky “Me Against the Music,” the album’s lead single, which was highly-anticipated and well received by fans, but failed to end her commercial dry spell, peaking at No. 35 on the Hot 100. 

Released a month after “Music,” Zone dabbled in hip-hop (“Outrageous”), pulsating euro-pop (“Breathe on Me”) and delicate slow songs (“Everytime,” soon to become her signature ballad). Most importantly, tucked six tracks deep on the album was “Toxic,” a theatrical dance-pop track with producers Bloodshy & Avant, led by a thick guitar line and Bollywood strings sample. Spears reportedly fought with her label to release the track as the album’s second single in early 2004 — and in the end, her vision paid off. The hit reached No. 9 on the Hot 100 and won best dance recording at the 2004 Grammys, marking her first (and to date only) win. It remains perhaps the most critically acclaimed three minutes and eighteen seconds of Britney’s career, and was ranked earlier this year as the Billboard staff’s No. 1 song of 2004. The companion video saw secret agent Spears dress as a stewardess, slither around in nothing but diamonds and poison her boyfriend, quickly becoming one of her most beloved visuals. 

At a time when it wasn’t cool to like Britney, “Toxic” shifted that narrative. Even though the world still regarded her and pop idol counterparts as record label puppets, she was nothing close to it — calling the shots on single releases and collaborators, and pushing back on the head honcho executives several times during this campaign. She ran with that agency and never looked back. Behind closed doors, though, things were starting to unravel. An impromptu visit to Las Vegas to marry her childhood friend Jason Allen Alexander caused concern. The union was annulled 55 hours afterward. Then, the overworked star suffered a leg injury while filming the video for “Outrageous” during a rare break in between dates of her “Onyx Hotel World Tour,” forcing her to cancel the rest of the trek and altering her performance ability forever.

The next few years for Spears were, well, chaotic, to say the least. Her romance with backup dancer-turned-husband Kevin Federline (and their subsequent reality show together) was heating up and the star shifted her perspective. The gloves were off and she was going to do as she pleased, both personally and professionally. Though she never earned the public’s stamp of approval for the relationship, Miss American Dream found ways of owning her decisions and clapping back with her music. A cover of Bobby Brown’s 1988 hit, “My Prerogative,” fronted her first compilation: 2004’s Greatest Hits: My Prerogative, while the eerie “Mona Lisa” foreshadowed her looming troubles. With only hours left until 2005, she dropped by Los Angeles’ KIIS-FM unexpectedly to preview the track, revealing it to be part of a project titled The Original Doll. 

For the next few years, career priorities would take a backseat as she and Federline welcomed two children, Sean Preston and Jayden James — but the unrelenting attention of the paparazzi increased and the star became the go-to cover girl for tabloid culture. Juggling motherhood, laying the groundwork for her next album and an eventual divorce from K-Fed put her at the eye of the gossip media storm, helping fuel the rise of outlets like Perez Hilton, TMZ and X17. Embarrassing and intrusive coverage of her led to headlines labeling her an unfit parent, while flashbulb moments like her shaving her head or attacking a paparazzo’s car with an umbrella turned her into a source for national mockery — but in the middle of the madness, Spears frequented nightclubs for inspiration, while recording what was to become her next album, 2007’s Blackout. For the first time in her career, there was no one to reel her in and she took agency, serving as executive producer of the project and exploring new sonic directions and collaborators. 

The result? Her magnum opus — demanding the attention of her peers, including Beyoncé and Rihanna, and the rest of the public eye. To this day, Blackout is still celebrated as an influential record for its edgy electro-pop sound and confidently sexual lyrics, and the album was even added to the Rock and Roll Hall of Fame’s musical library and archive in 2012. Brash, experimental and self-aware in its almost-menacing approach, the set was fronted by the Danja-produced “Gimme More,” where the star asserted her celebrity with a seismic three-word intro: “It’s Britney, bitch.” The song reached No. 3 on the Hot 100 — a massive win, considering it followed a lethargic comeback performance of the track on the VMA stage that year that saw her body-shamed and ridiculed. 

Despite the universally panned performance and continued public derision of Spears’ personal life in the media, Blackout still sold 290,000 copies in its first week and bowed at No. 2 on the Billboard 200. Even with sizable hits on her hands like the media clapback “Piece of Me” (a top 15 Hot 100 hit, and also her first VMA win for video of the year the next September), her personal life was imploding. She lost physical custody of her sons, while separately, parents Jamie and Lynn Spears (and soon-to-be business manager Lou Taylor) orchestrated a conservatorship over her personhood and estate after putting the singer on a 5150 involuntary psychiatric hold under California state law. The temporary-turned-permanent arrangement declared Britney was incapable of managing her financial affairs and making basic life decisions, but her workload over the following years would prove otherwise.

With all autonomy lost, Spears was pushed to work almost immediately, and everyone turned a blind eye to her restricted freedom as she hit the gym with fresh blonde extensions. She appeared on CBS’ How I Met Your Mother, helping the series log its highest ratings ever, and began recording yet another album, Circus. The 2008 project and its promo cycle was marketed as her return to form, a comeback project to redeem her from the turbulence of recent years — and released on her birthday, no less. It produced the lead single, “Womanizer,” which brought her back to the top of the Hot 100 for the first time since “…Baby One More Time.” She was smiling, in-shape and seemingly happy — and the success continued with follow-up singles: the dance-ready title track (a No. 3 hit) and the cheeky “If U Seek Amy” (No. 19). 

The subsequent Circus Starring Britney Spears Tour made its way around the world, but much like an actual circus, the star of the show was being mistreated. A growing disconnect between Spears and her craft became evident in music and performances, showing up more prominently throughout her following releases. Her next album, Femme Fatale, which dropped in 2011, embraced the EDM trend of the early 2010s. While the hits kept on coming (“Hold it Against Me,” No. 1; “Till the World Ends,” with a much-hyped remix featuring Nicki Minaj and Ke$ha, No. 3; and “I Wanna Go,” No. 7), the charm and charisma was starting to lose its spark in her performances and the impact of the conservatorship had taken its toll. Her appearance on Rihanna’s “S&M” remix and “Scream & Shout,” alongside will.i.am, extended her streak of hits, but she was about to run another victory lap and change the face of Las Vegas entertainment forever — whether she liked it or not. 

After years of releasing albums and counterpart tours, Spears’ next move revitalized both her career and the Las Vegas entertainment scene. Once a refuge for singers looking to relive their glory days, Sin City was given a facelift when her 2013 residency landed and she became the first contemporary act of her time to hit the strip. Aptly titled Britney: Piece of Me, the 90-minute show featured more than two dozen hits, incorporating classics and fan favorites, with the bells and whistles of her typical pop production. The show debuted weeks before the release of Britney Jean, a makeshift album marketed as her most personal project to-date, yet only produced a medium-sized hit with the campy “Work Bitch” and drew middling reviews. 

While still a contrast from the performer she once was, the residency saw Spears slowly come into her own again, running for four years and grossing $137.7 million. And for a fleeting moment, Britney Spears was Britney Spears again – with her million-dollar smile, dancing to a medley of hits at the 2016 Billboard Music Awards, where she also became the third recipient of the BBMA Millennium Award honor. Towards the latter part of the Vegas residency, the singer dropped 2016’s Glory, her last studio album to date, and it sounded like the spark was back: The collection was led by Weeknd-esque “Make Me,” featuring G-Eazy, and followed by a remix of “Slumber Party” with then-newcomer Tinashe. Those singles didn’t become the enduring hits of her ’00s albums, but Glory received strong reviews and served as an invaluable experience for the star, who later described it as “the one thing … that [she] really put her heart into” during her decade-plus conservatorship. 

Once the residency wrapped, Spears was seemingly gaining her autonomy back, but a reported dance rehearsal dispute with her father led to the cancellation of a follow-up Vegas residency, Britney: Domination. One red flag led to another and eventually a whistleblower alleged that she had been forced into a mental health facility against her will  — and the Free Britney movement was born. Court documents and (most fascinatingly) her Instagram account suddenly became sources to fans for possible clues and hints about her true feelings, turning the conspiracy theory into a full blown pop culture movement, garnering support from other pop icons like Miley Cyrus and Cher. In 2021, the Framing Britney Spears documentary brought more attention, while fan-orchestrated protests outside of court and a brighter spotlight on conservatorship abuse eventually helped Spears secure the right to choose her own legal representation and dismantle the arrangement. Since then, Spears has also told her story on her own terms in her memoir, The Woman in Me, in 2023. The bombshell tell-all sold 1.1 million copies and became a New York Times best-seller within a week of its release. A film adaptation of the book directed by Jon M. Chu is currently in the works at Universal Pictures.

The future of Spears’ pop superstardom since ending the 13-year conservatorship remains in question. Since giving up her childhood to an industry that overlooked her creative vision and discounted her achievements, she’s focused on a different chapter of life. Today, she lives a life free from the shackles of her family and the guardianship, and is relearning just how to be an independent adult. For that, she stands as a survivor and perhaps a reluctant hero to many – one whose hits, performances and aesthetic have had an incalculable influence on the last 25 years of pop culture. 

Her 2022 Elton John teamup “Hold Me Closer” is her lone hit since the Glory cycle, yet her impact is still alive and well in 2024, even shaping a fresh new batch of stars. Just take a look at this year’s VMAs ceremonies, where countless new-gen pop stars, including Sabrina Carpenter, Tate McCrae and Megan Thee Stallion, incorporated allusions to classic Britney in their appearances and performances. It’s that multigenerational legacy that’s helped Spears become one of the few acts to span top 10 hits across four decades, further cementing her legacy as one of pop’s greatest. Now that she’s achieved her independence and control over her career, whether she’ll make a full return to pop music remains unclear — we only know that if and when she does, the entire pop world will be rapt in attention to watch Britney Spears do it again.

Read more about the Greatest Pop Stars of the 21st Century here — and be sure to check back Tuesday as we kick off the top five with our No. 5 artist!

THE LIST SO FAR:

Honorable Mentions

25. Katy Perry
24. Ed Sheeran
23. Bad Bunny
22. One Direction
21. Lil Wayne
20. Bruno Mars
19. BTS
18. The Weeknd
17. Shakira
16. Jay-Z
15. Miley Cyrus
14. Justin Timberlake
13. Nicki Minaj
12. Eminem
11. Usher
10. Adele
9. Ariana Grande
8. Justin Bieber
7. Kanye West
6. Britney Spears