With the first quarter of the 21st century coming to a close, Billboard has spent the last 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 Taylor Swift, who took pop stardom to places we hadn’t previously thought possible. (Hear more discussion of Taylor Swift and explanation of her list ranking on our Greatest Pop Stars podcast — with her episode debuting Wednesday — and see our recently rebuilt list of the Greatest Pop Star by Year from 1981 to 2023 here.)
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It’s amusing to think back on Taylor Swift at age 17, staring straight into Tim McGraw’s soul at the 2007 ACM Awards while performing her debut single – which just so happened to be named after him.
Pitchy but spirited, plucky but deeply promising as a songwriter, it was clear that she was bursting at the seams with talent and ambition – fully capable, in theory, of reaching the greatest heights a career in the music business could offer. But the audacity she demonstrated by taking the moniker of one of country’s biggest stars, claiming it for her own release – her first-ever, at that – and serenading him with it in front of all of their peers on live television? That proved she also had the sheer nerve she’d need to actually get there.
Time and time again, that same moxie would propel the Pennsylvania native to previously inconceivable heights, her profile skyrocketing with each album as she stacked up chart records, historic sales numbers and unprecedented Recording Academy recognition. Through honoring all the traits that made her different – her sharp pen, her relatable girl-next-door awkwardness, her hopeless romanticism – and rejecting culture’s previous expectations for female artists to be overtly sexy, pliable and cool, she was able to forcefully, gravitationally bend culture to her will and become one of the world’s biggest undisputed pop stars, despite her eight-year late start in country music.
She is the only person to ever win album of the year at the Grammys four times. She has the second-most Billboard Hot 100 entries of all time (only Drake has more) and ties with Jay-Z for second-most No. 1 albums on the Billboard 200 (bested only by The Beatles). She is one of the most impressive touring artists of the past quarter-century, a status that has culminated with her global Eras Tour becoming the highest-grossing trek of all time in 2023, just halfway through its run, as it repeatedly set stadium attendance records and boosted local economies in its confetti-and-friendship-bracelet-strewn wake. She’s a billionaire, the only female artist to become one predominantly through music alone. She is the most famous woman in the world.
And, with all due respect to Tim McGraw, the first thing millions of young pop fans really do think of when they hear his name is Taylor Swift.
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Swift and her fans were both young when they first saw each other, she an angel-faced teenager with corkscrew curls and lofty dreams that spilled over into both songs and MySpace posts, they a pack of mostly adolescent girls who pored over her interviews, replayed her vlogs long before “vlogging” was even a thing and started picking up guitars at higher rates to emulate their beloved heroine. The details of her origin story are now common bits of trivia — she was born Dec. 13, 1989 to Scott and Andrea Swift, raised on a Christmas tree farm in Wyomissing, and did you know her lucky number is 13? — but they used to make up the sacred web of knowledge held dear by her earliest admirers. To them, the tale of what happened next is also etched into memory like a bible passage: She moved to Nashville as a teenager to pursue a country music career, scored a publishing deal while still a student at Hendersonville High School and later got her big break when Scott Borchetta discovered her at the Bluebird Café and signed her to his infant label Big Machine Records.
In 2006, she dropped her self-titled debut LP through Big Machine and promoted it heavily, embarking on radio tours and hand-packing her own CDs into envelopes to personally send off to stations. She performed constantly — later joining Rascal Flatts, George Strait, Brad Paisley, Faith Hill and, yes, Tim McGraw as an opener on their respective country tours – and she was already demonstrating an instinctual business savvy that’s uncommon in most creatives, let alone ones who are still just 16. As an incentive for fans to buy copies of the record, for instance, she started planting hidden messages in her CD lyric booklets hinting at the real-life inspirations behind her songs, a tradition that would continue on future albums and grow more tantalizing as her subjects became more famous.
The specifics of this era feel fuzzier now that Swift has been ubiquitous for years — especially when, in 2024, modern stars find fame seemingly overnight through the lightning strike of social media virality as opposed to slowly, steadily building their fanbases over time. But her early career was much more of an old-school, brick-by-brick climb up the ranks than we often give her credit for now, fueled by the fact that on Taylor Swift, she was already composing with the skill of an experienced career songwriter who had a particular knack for connecting with young girls – because, well, she still was one herself.
Lead single “Tim McGraw” became Swift’s first entry on the Hot 100 that September, and the following year, the heart-rending “Teardrops on My Guitar” and the maniacally catchy “Our Song” also made their way up the chart. Neither of those would reach their peaks until 2008, though, when fiery breakup bangers “Should’ve Said No” and “Picture to Burn” also entered and became top 40 hits, just in time to capture everyone’s attentions ahead of the release of Fearless in November. She was a darling in the insular world of country music, earning professional recognition from the CMAs and ACMs, but she was becoming a face people recognized in pop culture, too. It was around this time that she was embraced into Miley Cyrus and Selena Gomez’s Disney star ranks and briefly dated Joe Jonas, her first of several tabloid-feeding romances that would become central to the way we think and talk about her persona. People were looking – she just needed to stick the landing with her next album.
Again, the magnitude of the entire Fearless era is hard to conceptualize now that Swift has dwarfed herself so many times over the years. But in late 2008, the musician officially exploded into crossover-star status thanks to the staggering success of her sophomore album – which spent an incredible 11 weeks at No. 1 on the Billboard 200 and sold 592,000 million copies in its first week. She dominated radio with country-pop smashes that remain classics in her discography to this day – most notably, “Love Story” and “You Belong With Me,” two top five Hot 100 hits with cinematic music videos that inspired some of the most memorable moments in her iconography — and she became the ultimate it-girl, whose face you craned your neck to see on red carpets, talk shows, magazine covers. The very first headlining trek she ever embarked on, the Fearless Tour, was through arenas, and she capped the triumphant era with a headline-grabbing album of the year win at the 2010 Grammys, at that point the youngest artist to ever do so.
The most talked-about moment from the first of Swift’s many imperial phases, though, was none of the above — but you probably already know where this is going. Like Shakespearean foils crossing paths for the first time, Kanye West fatefully thrust himself into the then-19-year-old Swift’s storyline, publicly declaring at the 2009 VMAs that she actually didn’t deserve one of the countless awards she would take home that year and leaving her shellshocked on stage in a moment that would catapult her into the international news cycle for weeks to come. Everyone from Dr. Phil to President Barack Obama had an opinion on the matter, with the latter famously declaring the rapper to be “a jacka–.”
Now, to look at the trajectory Swift was already on up until this point and still argue that the VMAs incident “made [her] famous,” as Ye would later claim, is laughable. But his protests at the show would foreshadow so many others coming for her down the line – namely, questions about her overall worthiness as an awards powerhouse, as debates raged over whether such a young (and female) performer was actually writing her own songs, or merely coasting off the contributions of her older male collaborators.
In response to those criticisms, she would pen the entirety of her 2010 follow-up album, Speak Now, without any outside lyrical help, resulting in a magical 14-track romantic dreamscape that remains a fervent fan-favorite to this day. If Fearless showcased her ability to craft hooky, accessible earworms, her third studio effort introduced her gift for penning deeply personal, woundingly emotional ballads like “Back to December,” “Dear John” and “Last Kiss,” a trade most important to the DNA of Swift’s musical genius.
Though it spent six weeks at No. 1 and helped make Swift Billboard’s then-youngest Woman of the Year, Speak Now didn’t spawn the same level of pop smashes, critical acclaim or Grammy love as its older sister did. When she made 2012’s Red, she seemed determined to make up for its lack of universality, enlisting the help of pop-music godfathers Max Martin and Shellback to push her sound up to the absolute barrier of pop, while staying just country enough to hold onto her identity and keep Big Machine happy. It worked: the deliberately cloying “We Are Never Ever Getting Back Together” became her first-ever No. 1 hit on the Hot 100, and with numerous top 40 smashes (“I Knew You Were Trouble,” “22” and “Begin Again,” to name a few), the project had double the capacity for hits as Fearless. Slower, more intimate tracks like “The Last Time,” “I Almost Do” and crown jewel “All Too Well” also expanded on the confessional sad-girl oeuvre she’d started with Speak Now, making Red a beautiful hodgepodge of all the best parts of both albums that crystallized what we now recognize as Swift’s greatest contributions to modern music: catchy hooks and heartbreaking ballads.
When Red also failed to take home album of the year at the Grammys, and her self-described “break my heart and I’ll write a song about you” schtick started to be met with antagonism – as Swift later explained, she became a “national lightning rod for slut-shaming” — she once again sought to level up. Breaking almost entirely away from her longtime Nashville collaborators and assembling a top 40 dream team comprised of Martin, Shellback, Ryan Tedder and newbie producer Jack Antonoff, the increasingly self-assured artist narrowed her focus on making an unabashed pop album that exploded with energy and shimmering ‘80s synths. She chose singles centered less on boys and more around moving to New York (which she did around that time), feuding with a frenemy (ahem, Katy Perry) and shaking off the haters. It was a colossal success by every metric. Thus began imperial phase no. 2: 1989.
Swift was downright inescapable at this point, with 1989 selling 1.29 million copies in its first week and reigning atop the Billboard 200 for 11 weeks. Her dominion was powered by an impeccable single and music video run, with “Shake It Off,” “Blank Space” and “Bad Blood” all spending time at No. 1 while “Out of the Woods,” “Style” and “Wildest Dreams” held down her rule over radio and department-store speakers for years after the fact. She embarked on her first-ever stadium tour, on which she often brought out guest artists and random famous friends from her #Squad – the innerworkings of which were constantly being dissected by fans and gossip sites alike, both boosting Swift’s fame and narrowing the microscope on her body, style, decisions and personal life. She became Billboard’s first-ever two-time Woman of the Year while making history as the youngest musician to ever take home album of the year at the Grammys twice.
She was Caesar, finally ascending the throne, her ambition and tunnel vision at last giving way to more success than even she could’ve dreamed of. But she hadn’t gotten there with the amount of support and trust she’d hoped from her advisers at Big Machine, who she has insinuated dragged their feet on every step of her country departure. Meanwhile, someone else was preparing to reenter the picture, a sharp knife strapped to his Yeezys.
When public opinion tilted in Ye’s favor following the Great Phone Call Dispute of 2016, Swift responded to the chorus of voices undermining her — fellow celebrities and people behind the scenes included — by hiding away. After a year of self-imposed solitude in London, during which time she fell in love with actor Joe Alwyn, the singer re-emerged in November 2017 with Reputation, one of her most pointed creative risks to date. The dark, theatrical LP found Swift truly reclaiming her narrative and explaining her side of a controversy in detail for the first time in her career, a sharp swerve from her previous method of staying quiet and letting the public decide what she was thinking for her. She would never again be the girl in the silver gown, stunned into silence on the VMAs stage.
As soon as her six-album contract was up with Reputation, Swift split from Big Machine and signed with Republic, at the time only hinting at the reason behind her decision: “Incredibly exciting to know that I’ll own all of my master recordings that I make from now on,” she wrote on Instagram. But the signs that she’d been quietly battling her own label for years were there; with 1989, she was open about how hard she’d had to fight Borchetta to let her release a pop album, and on the Reputation Tour, a dedication to Loie Fuller, who “fought for artists to own their own work,” was shown onscreen each night.
By the time the situation exploded with the sale of Big Machine — and with it, her master recordings — to Scooter Braun in 2019, Swift had already turned in Lover. As we’d learn later in her 2020 Netflix film Miss Americana, she felt that, at 29, this project was her last chance to reach audiences on a global scale before she aged out of pop stardom. This fear seemed to lead to her releasing “Me!” — a slightly juvenile and generic pop track that documentary footage would later show she wrote not with the ambition of living up to her own pop genius, but with the quaint goal of little kids singing along — instead of the LP’s clear pop banger, future four-week No. 1 “Cruel Summer,” as its lead single. The most important part of the Lover era to Swift’s overall legacy is that she finally started using her immeasurable influence for political causes after a decade of silence, championing the LGBTQ community through “You Need to Calm Down” and endorsing Tennessee Democrat Phil Bredesen for U.S. senate over Republican opponent Marsha Blackburn.
But when Scootergate happened, a fire was lit under her. She issued scathing response after scathing response, making her fury abundantly clear and quickly publicizing her intention to re-record her first six albums in order to reclaim ownership of her past works. While waiting for the clock to run out on the legal barriers blocking her from doing so before November 2020 – and after the COVID-19 pandemic sidelined her plans for the continuation of the Lover era, including a limited run of performances dubbed “Lover Fest” – she surprise-dropped Folklore and Evermore. Un-muddled by months of pre-release rollout or the need for flashy singles or visual moments, the back-to-back albums reminded the general public that her true gift lies in her storytelling — and thanks in part to an understated acoustic-folk sound assisted by The National’s Aaron Dessner, they made Swift “cool” to an entire audience that had never seen her that way before. In 2021, Folklore gave her a record-tying third AOTY win at the Grammys.
The first piece of imperial phase no. 3 fell into place that April. With the unveiling of her Fearless (Taylor’s Version) re-recording, Swift took her first steps on an escalator that, at the close of the quarter-century, is still going up, sharing a near-exact replica of the album that made her a household name with the additions of never-released songs she wrote and recorded more than 15 years prior. Following that same formula each time, the re-records have only ramped up in cultural significance as they’ve progressed; Red (Taylor’s Version) spawned history’s longest song to go No. 1 with fans’ beloved “All Too Well (10 Minute Version)”; Speak Now (Taylor’s Version) outsold its predecessor by 138k units in its first week; and 1989 (Taylor’s Version) became the first re-record to outsell its original counterpart, blowing the already staggering first-week numbers of 2014’s 1989 out of the water with 1.36 million.
The beauty of the re-recordings was that they both allowed longtime fans to relive some of their best memories with Swift while giving newer fans – or simply outsiders who weren’t paying much attention the first time these albums rolled around – a second chance at experiencing her most quintessential eras in real time. But arguably the most shocking part of the process was the fact that, in between the Taylor’s Versions, she was still recording original music. She dropped Midnights in 2022, moving a jaw-dropping 1.58 million first-week units and spawning her longest-running No. 1 hit with “Anti-Hero” — the most honest she’s ever been in her music about her personal demons and incomprehensible station in life — while making chart history, as the first artist to ever simultaneously occupy the entire top 10 of the Hot 100, not to mention winning a record-setting fourth AOTY Grammy.
By the time she embarked on her global Eras Tour, interest in her body of work — old songs and brand new — had never been higher, and like the mirror ball she is, Swift has rewarded fans for it every night on the road with more than three hours’ worth of over-the-top scream-your-face-off catharsis, each show an homage to the painstaking career she’s built, brick by brick, one beautiful, messy era at a time. The unprecedented scale of the tour aligns with the absolutely unfathomable reach she’s achieved in 2023 and onward, her victory lap only continuing with the introductions of boyfriend Travis Kelce to the fairytale – through which she’s also captivated the NFL, proving that no major institution is off limits for her to take over — and the release of 12-week Billboard 200-topper The Tortured Poets Department. The dense 31-track blockbuster LP is second only to Adele’s 25 in highest first-week sales of all time (2.6 million) and has once again swept nominations in every major Grammy category for Swift in 2025, including what could be a record-extending album of the year.
Last year, she was Billboard’s Greatest Pop Star of 2023, making her the only artist to ever win the title in three separate years (following 2015 and 2021), but the run she’s had in the past biennium isn’t just the grandest of her own career; it’s also possibly the most extraordinary cultural supremacy any of us have ever seen one artist accomplish in our lives. Her decisions, whereabouts and opinions are all considered public domain – you’re out of the loop if you haven’t seen what she wore to the latest Kansas City Chiefs game – and there is no reason to believe that if she dropped another album tomorrow, it wouldn’t invariably end up spending more weeks at No. 1 on the charts than even Tortured Poets, because when hasn’t she been able to top herself? Nothing is out of the realm of possibility for her.
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All of this to say, the star is still outdoing herself, still beating her own unbeatable feats, still forging ahead in the same uncharted direction when most others would’ve long since burned out or jumped ship to alternative career paths – all of which, it shouldn’t go without saying, is exceedingly rare for someone nearly 20 long years into their career. She is venerated by the greats who came before her, from Paul McCartney and Ringo Starr — who declared that Swift’s mega-popularity is the closest phenomenon to Beatlemania he’s ever seen – to Stevie Nicks, Dolly Parton and Carole King. At just 34 years old, her catalog has inspired college courses all over the world that treat her written word with the same level of analysis as Wordsworth, and her business innovations – be it the album variations she’s been experimenting with since 1989’s collectible Polaroid sets, her negotiations with Spotify and Apple Music for fairer streaming rates or the playbook she’s still writing on how to re-release old music to new blockbuster returns – will continue to have reverberations throughout the industry, for longer than we can probably even currently imagine.
For all these reasons and so many more, she is Billboard’s No. 2 Greatest Pop Star of the 21st century, blowing past countless other accomplished hitmakers and icons. The fact that controversy will likely tear through the internet over her being just one small space below No. 1 is just another testament to her power, but regardless, her placement shouldn’t leave Swifties upset for too long — especially considering how much later in the millennium she got her start, both in the genre and music in general. In a way, Swift has always been like pop’s most curious tourist, never quite feeling like she’d always belonged there, more so trying on the things she liked best about the territory and sticking to her own guns for the rest. Instead of coming up and thriving naturally within the bounds of what we understand pop to be then and now, she rewrote the genre in her own image and, in doing so, charted a new course for crossover success that countless other confessional singer-songwriters like Olivia Rodrigo, Phoebe Bridgers, Gracie Abrams have since benefitted from.
That’s a lot more than tween Taylor bargained for when she wrote on her first album that she was “just a girl, trying to find a place in this world.” And if what her history has told us remains true, she’s still just getting started.
Read more about the Greatest Pop Stars of the 21st Century here — find our accompanying podcast deep dives and ranking explanations here — and be sure to check back next Tuesday (Dec. 3) as we unveil our No. 1 Greatest Pop Star of the Century so far!
THE LIST SO FAR:
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
5. Lady Gaga
4. Drake
3. Rihanna
2. Taylor Swift
