Billboard’s Greatest Pop Stars of the 21st Century: No. 2 — Taylor Swift

Billboard has spent the past few months tallying our staff’s selections for the top 25 pop stars of the past 25 years as the first quarter of the twenty-first century draws to a close. The stars that have made our list thus far are listed below. Next, we look at Taylor Swift, who has elevated pop success to heights we never would have imagined. (See our recently redesigned list of the Greatest Pop Star by Year from 1981 to 2023 here, and listen to our Taylor Swift Greatest Pop Stars podcast episode for more discussion of Taylor Swift and an explanation of her rating.)

 

 

 

It’s funny to remember Taylor Swift at the age of 17 playing her debut track, which was titled after Tim McGraw, at the 2007 ACM Awards, looking directly into his soul.

It was obvious that she was bursting at the seams with skill and drive, pitchy but lively, brave yet incredibly promising as a songwriter. Theoretically, she was totally capable of achieving the highest levels that a career in the music industry could give. But what about the boldness with which she took the name of one of the biggest performers in the country, claimed it for her own release (her first, at that), and serenaded him with it in front of all their peers on live television? That demonstrated that she also possessed the simple courage required to succeed.

With each album, the Pennsylvania native’s popularity soared as she piled up chart records, historic sales figures, and unheard-of Recording Academy acclaim. Time and again, the same moxie would catapult her to previously unthinkable heights. Despite her eight-year late start in country music, she was able to forcefully and gravitationally bend culture to her will and become one of the biggest undisputed pop stars in the world by embracing all the qualities that made her unique, such as her sharp pen, relatable girl-next-door awkwardness, and hopeless romanticism, and by rejecting the previous expectations placed on female artists to be overtly sexy, pliable, and cool.

She is the only individual to have won four Grammy Awards for album of the year. She is tied with Jay-Z for the second-most No. 1 albums on the Billboard 200 (only surpassed by The Beatles), and she has the second-most Billboard Hot 100 entries of all time (only Drake has more). Her status as one of the most remarkable touring performers of the last 25 years has culminated in her global Eras Tour becoming the highest-grossing journey of all time in 2023, just halfway through its run. In the wake of her tour, which was littered with confetti and friendship bracelets, she set numerous attendance records at stadiums and boosted local economies. She is the only female musician to achieve the status of a billionaire solely via her music. She is the world’s most well-known female.

With all due respect to Tim McGraw, millions of young pop fans actually think of Taylor Swift first when they hear his name.

 

 

 

When Swift and her fans first met, they were both young. Swift was an angel-faced teen with corkscrew curls and big dreams that showed in her songs and MySpace posts. Her fans were mostly teenage girls who watched her interviews, watched her vlogs before the term “vlogging” existed, and began picking up guitars more frequently in an attempt to imitate their favorite heroine. Although the specifics of her birth story are now conventional trivia—she was born on December 13, 1989, to Scott and Andrea Swift, grew up on a Wyomissing Christmas tree farm, and did you know that 13 is her lucky number?—they formerly comprised the hallowed web of knowledge that her early fans held in high regard. She moved to Nashville as a teenager to pursue a career in country music, secured a publishing deal while still a student at Hendersonville High School, and then got her big break when Scott Borchetta found her at the Bluebird Café and signed her to his fledgling label Big Machine Records. For them, the story of what transpired next is also inscribed in their memories like a passage from the Bible.

Her self-titled first album was released by Big Machine in 2006, and she actively promoted it by going on radio tours and individually packaging her own CDs into envelopes to deliver to radio stations. She performed frequently, eventually opening for artists like Faith Hill, Brad Paisley, George Strait, Rascal Flatts, and yes, Tim McGraw on their respective country tours. She was already exhibiting an innate business acumen that is unusual for most creatives, much less one who is only sixteen. For example, she began inserting secret messages in her CD lyric booklets that alluded to the real-life inspirations of her songs as a way to entice fans to purchase copies of the record. This practice would be repeated on subsequent albums and would become increasingly alluring as her subjects gained greater notoriety.

Since Swift has been so popular for years, the details of this era are less clear, particularly in 2024 when contemporary stars gain notoriety almost instantly through social media virality rather than gradually and steadily growing their fan bases over time. She was already writing songs for Taylor Swift with the skill of an experienced career songwriter who had a special knack for connecting with young girls—because, well, she was still one herself—so her early career was much more of an old-school, brick-by-brick ascent up the ranks than we often give her credit for today.

That September, Swift’s lead single “Tim McGraw” marked her first appearance on the Hot 100. The following year, the heartbreaking “Teardrops on My Guitar” and the insanely catchy “Our Song” also rose to the top of the chart. However, neither of those would peak until 2008, when the smoldering breakup hits “Should’ve Said No” and “Picture to Burn” also made an appearance and made it into the top 40, right before Fearless’ November release. She gained professional acclaim from the CMAs and ACMs, making her a darling in the exclusive world of country music, but she was also starting to get awareness in pop culture. Around this time, she was accepted into the Disney star ranks of Selena Gomez and Miley Cyrus, and she had her first of many tabloid-feeding relationships that would shape our perceptions of her. She also had a brief relationship with Joe Jonas. She only needed to make a strong impression with her upcoming record since people were watching.

Once more, given how many times Swift has shrunk herself over the years, it is difficult to imagine the scope of the entire Fearless era. However, the startling success of her sophomore album, which sold 592,000 copies in its first week and spent an amazing 11 weeks at No. 1 on the Billboard 200, propelled the musician into crossover-star status in late 2008. She became the ultimate it-girl, whose face you craned your neck to see on red carpets, talk shows, and magazine covers. She dominated radio with country-pop hits that are still classics in her discography, including “Love Story” and “You Belong With Me,” two top five Hot 100 hits with dramatic music videos that inspired some of the most memorable moments in her iconography. She completed the glorious era with a headline album of the year win at the 2010 Grammys, capping off her first headlining tour ever, the Fearless Tour, which took place in arenas.

 

However, none of the foregoing was the most talked-about event from Swift’s first of his many imperial periods, but you probably already know where this is heading. Kanye West tragically threw himself into Swift’s storyline at the 2009 VMAs, publicly stating that she didn’t deserve one of the many awards she would win that year and leaving her stunned on stage in a moment that would propel her into the global news cycle for weeks to come. It was like Shakespearean foils first meeting. Everybody has an opinion on the subject, including President Barack Obama, who memorably called the rapper “a jacka–” and Dr. Phil.

It is absurd to consider Swift’s trajectory up to this point and yet maintain that the VMAs event “made [her] famous,” as Ye would subsequently assert. However, his protests during the show would foreshadow many more that would follow, including questions about her overall deservingness as a major force in the awards industry, as arguments raged over whether the young (and female) performer was truly writing her own songs or was just profiting from the work of her older male collaborators.

She would write the whole 2010 follow-up album, Speak Now, without any outside lyrical assistance in reaction to those criticisms, creating a gorgeous 14-track love dreamscape that is still a devoted fan favorite today. If her third studio album demonstrated her talent for writing incredibly intimate, heartbreakingly emotional songs like “Back to December,” “Dear John,” and “Last Kiss,” Fearless demonstrated her ability to create catchy, approachable earworms. This talent is crucial to Swift’s artistic creativity.

Speak Now didn’t produce as many pop hits, as much critical acclaim, or as many Grammys as its older sister, despite spending six weeks at the top of the charts and helping Swift become Billboard’s then-youngest Woman of the Year. She appeared intent on making up for its lack of general appeal when she recorded “Red” in 2012, enlisting the aid of pop music icons Max Martin and Shellback to elevate her sound to the pinnacle of pop while being sufficiently country to maintain her identity and satisfy Big Machine. It worked: with many top 40 singles, including “I Knew You Were Trouble,” “22,” and “Begin Again,” the project had twice the potential for hits as Fearless, and the purposefully corny “We Are Never Ever Getting Back Together” became her first-ever No. 1 success on the Hot 100. The confessional sad-girl oeuvre that Swift had begun with Speak Now was further developed by slower, more personal songs like “The Last Time,” “I Almost Do,” and the album’s crown jewel, “All Too Well.” Red was a stunning mashup of the best elements of both albums, encapsulating what we now know to be Swift’s greatest contributions to contemporary music: catchy hooks and heartbreaking ballads.

 

 

Swift subsequently clarified that she became a “national lightning rod for slut-shaming” after Red’s self-proclaimed “break my heart and I’ll write a song about you” schtick began to elicit hostility after she failed to win album of the year at the Grammys. The increasingly confident artist focused on creating an unabashed pop album that exploded with energy and shimmering ’80s synths, breaking almost entirely with her longtime Nashville collaborators and assembling a top 40 dream team that included Martin, Shellback, Ryan Tedder, and up-and-coming producer Jack Antonoff. She picked songs that were less about boys and more about relocating to New York, which she did at the time, fighting a rival (Katy Perry, for example), and overcoming the detractors. By all measures, it was an enormous success. Thus, the second imperial phase, 1989, began.

With 1989 selling 1.29 million copies in its first week and topping the Billboard 200 for 11 weeks, Swift was now unavoidable. “Out of the Woods,” “Style,” and “Wildest Dreams” maintained her control over radio and department store speakers for years after the fact, while “Shake It Off,” “Blank Space,” and “Bad Blood” all spent time at No. 1. Her dominance was fueled by an outstanding run of singles and music videos. She started her first stadium tour, frequently bringing in guests and random well-known friends from her #Squad. Fans and gossip websites were always analyzing the inner workings of this tour, which increased Swift’s notoriety and focused more on her personal life, decisions, style, and body. She became the youngest artist to win album of the year at the Grammys twice and became the first-ever two-time Woman of the Year on Billboard.

At last, her ambition and tunnel vision gave way to greater success than she could have ever imagined, and she was Caesar, taking the throne. Her counselors at Big Machine, who she implied dragged their feet on every stage of her country exit, had not given her the support and trust she had hoped for. Someone else, with a sharp knife strapped to his Yeezys, was getting ready to reenter the scene.

Swift reacted to the chorus of voices criticizing her, including those from behind the scenes and other celebrities, by withdrawing after public opinion shifted in Ye’s favor during the Great Phone Call Dispute of 2016. The singer resurfaced in November 2017 with Reputation, one of her most daring creative risks to date, following a year of self-imposed seclusion in London, during which she fell in love with actor Joe Alwyn. For the first time in her career, Swift was able to fully recover her story and provide a detailed explanation of her side of a debate in the dark, theatrical LP. This marked a dramatic departure from her prior strategy of remaining silent and letting the audience determine her thoughts. The girl in the silver gown, startled into silence on the VMAs stage, would never be her again.

Swift left Big Machine and joined Republic as soon as her six-album deal with Reputation expired, at the time giving no indication of why she made the move: “Very exciting to know that I’ll own all of my master recordings that I make from now on,” she posted on Instagram. However, there were indications that she had been secretly fighting her own label for years; in 1989, she talked candidly about how difficult it had been to convince Borchetta to allow her to release a pop album, and every night on the Reputation Tour, a tribute to Loie Fuller, who “fought for artists to own their own work,” was shown onscreen.

Swift had already submitted Lover by the time the situation blew up in 2019 when she sold Big Machine, along with her master recordings, to Scooter Braun. She believed that, at the age of 29, this project was her final opportunity to reach a global audience before she grew out of pop stardom, as we would discover later in her 2020 Netflix film Miss Americana. This fear apparently caused her to release “Me!” as the lead single instead of the album’s obvious pop hit, future four-week No. 1 “Cruel Summer,” which is a somewhat juvenile and generic pop song that documentary footage would later reveal she wrote not with the ambition of living up to her own pop genius but with the charming goal of little kids singing along. The most significant aspect of Swift’s overall legacy during the Lover era is that, after ten years of silence, she began to use her immense influence for political causes. She supported Tennessee Democrat Phil Bredesen over Republican Marsha Blackburn for the U.S. senate and championed the LGBTQ community with “You Need to Calm Down.”

However, a fire was set beneath her when Scootergate occurred. In a series of harsh responses, she made her rage very evident and swiftly announced her plan to re-record her first six albums in order to regain control of her earlier creations. She unexpectedly released Folklore and Evermore while she waited for the legal restrictions that prevented her from doing so before November 2020 to expire. This was after the COVID-19 pandemic put a stop to her plans for the continuation of the Lover era, which included a limited run of performances called “Lover Fest.” Unconcerned with months of pre-release promotion or the requirement for dazzling singles or visuals, the consecutive albums served as a reminder to the public that Swift’s storytelling is her real talent. With the help of Aaron Dessner of The National and a subtle acoustic-folk sound, they helped make Swift “cool” to a whole audience that had never seen her that way before. She received a record-tying third AOTY award at the Grammys in 2021 from Folklore.

That April, the first component of Imperial Phase No. 3 came into being. Swift’s Fearless (Taylor’s Version) re-recording, which shares a nearly identical copy of the album that made her famous with the addition of unreleased songs she wrote and recorded more than 15 years ago, marked the beginning of an escalator that, at the end of the quarter-century, is still going up. Following the same formula each time, the re-records have only grown in cultural significance as they have progressed. For example, 1989 (Taylor’s Version) became the first re-record to outsell its original counterpart, surpassing the already astounding first-week sales of 2014’s 1989 by 1.36 million; Speak Now (Taylor’s Version) outsold its predecessor by 138k units in its first week; and Red (Taylor’s Version) gave birth to the longest song in history to reach the No. 1 spot with the beloved song “All Too Well (10 Minute Version)”; and so on.

The appeal of the re-recordings was that they gave new fans, or just those who weren’t paying much attention when these albums first came out, a second opportunity to experience Swift’s most iconic periods in real time while also enabling longtime fans to relive some of their favorite moments with her. Perhaps the most startling aspect of the process, however, was that she continued to record original music in between the Taylor’s Versions. She made chart history in 2022 when she released Midnights, which sold an astounding 1.58 million units in its first week and produced her longest-running No. 1 hit, “Anti-Hero,” which is the most honest song she has ever written about her personal demons and incomprehensible station in life. She also won a record-setting fourth AOTY Grammy.

 

Swift, like the mirror ball she is, has rewarded her fans for their support with over three hours of extravagant, scream-your-face-off catharsis every night on the road. Each show pays tribute to the meticulous career she has built, brick by brick, one beautiful, messy era at a time. By the time she started her global Eras Tour, interest in her body of work, including both old and brand-new songs, had never been higher. The tour’s unprecedented scope is in line with her unimaginably broad reach in 2023 and beyond. Her only victories have been the release of The Tortured Poets Department, a 15-week Billboard 200-topper, and the introduction of boyfriend Travis Kelce to the fairytale, through which she has also enthralled the NFL and demonstrated that no significant institution is off limits for her to take over. Swift’s dense 31-track blockbuster album has swept nominations in every major Grammy category in 2025, including what might be a record-extending fifth album of the year. It has the second-highest first-week sales of all time (2.6 million), second only to Adele’s 25.

In addition to being the only artist to win the title in three consecutive years (after 2015 and 2021), she was named Billboard’s Greatest Pop Star of 2023 last year. Her recent run is not only the most impressive of her career, but it may also be the most remarkable feat of cultural supremacy that any of us have ever witnessed in the lives of artists. There is no reason to think that if she released another album tomorrow, it wouldn’t inevitably spend more weeks at No. 1 on the charts than even Tortured Poets because she has consistently been able to outperform herself. Her choices, whereabouts, and opinions are all regarded as public domain; if you haven’t seen what she wore to the most recent Kansas City Chiefs game, you’re out of the loop. For her, there is nothing that is impossible.