Greatest Pop Stars of 21st Century

With the first quarter of the 21st century coming to an end, Billboard has been looking back on the 25 Greatest Pop Stars of the Past 25 Years. Below, we take a deeper look into the peak of our No. 24 pop star, Ed Sheeran, and how his writing style — while often critically derided — actually displays the efficiency, creativity and originality of a true songwriting savant.

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Despite being one of this century’s most successful musicians by pretty much any statistic you could conjure, Ed Sheeran’s music has inspired well over a decade’s worth of eye rolls and turned-up noses – not necessarily because it’s bad, in the eyes of critics, but because it’s boring.

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That’s not an oversimplification. In 2011, The Guardian’s Peter Robinson literally made the English singer-songwriter the face of “The New Boring,” calling his debut album + “a 12-bore s–tgun” and likening him to “a combination of every friend-of-a-friend’s band whose pub gig you have ever witnessed.” Six years later, Pitchfork’s Laura Snapes described Sheeran as “trite,” “bland” and “unimaginative,” all within the sub-headline of a review about his third album ÷ (it scored a 2.8). For the duration of his career, the musician has been especially critiqued for his approach to genre, cherry-picking features of hip-hop, R&B and rock and distilling them into compressed, radio-friendly pop earworms which inevitably become lodged for years at a time on the charts and on grocery store speakers — writer Rachel Aroesti recently described the end result as a “sludgy, vague, inoffensive post-genre sound that has served to homogenise music in general.”

It’s understandable why people might be so tempted to explain away Sheeran’s success. Homely, scruffy and pointedly underdressed, he soared into the general public’s consciousness as the total antithesis to the polished male pop stars who were big before him — Justins Timberlake and Bieber, One Direction, Bruno Mars – prompting confusion as to how exactly he was able to infiltrate their sleek ranks. But as the essays have piled up over the last 15 years dismissing his scrappy image and mass-appeal music as calculated ploys to maximize profit by appearing as relatable to consumers as possible, one salient quality of Sheeran’s superstardom seems to have fallen out of focus. His seamlessly packaging together the shiniest parts of different genres and presenting them in a way that’s almost universally palatable is a skill in and of itself, and one with which Sheeran is singularly gifted.

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It takes an intriguing musical vocabulary, for instance, to infuse a romantic folk ballad such as “Lego House,” one of Sheeran’s earliest hits, with mile-a-minute rap bars — “And it’s dark in a cold December/ But I’ve got you to keep me warm…” in the pre-chorus, without interrupting its cozy pacing. The same can be said of his 2014 smash “Sing,” which somehow has all the body and elasticity of a FutureSex/LoveSounds banger – producer Pharell Williams once told Billboard the Timberlake album was a key inspiration — while staying simultaneously grounded in acoustic instruments and Sheeran’s rapid-fire rhyming. Other hits like 2014’s R&B-rap-pop-dance number “Don’t” and 2017’s tropical 12-week Billboard Hot 100-topper “Shape of You” show off his proclivity for complementing catchy sung melodic hooks with percussive rap-based verses, which he can confidently weave in and out of without ever disrupting the overall feel of a song.

Though he’s never been the most prosaic writer, the words he does choose instead serve to fit snugly in rhyme pockets or push the momentum of a section forward. While certainly cheesy and not particularly clever, the lyrical and melodic simplicity of “I’m in love with the shape of you/ We push and pull like a magnet do/ Every day discovering something brand new” enables it to wedge instantly into listeners’ memories. On the verses, he creates pleasing, percussive toplines that aren’t weighed down by needless syllables, but still manage to propel the narrative forward by quickly summarizing storylines (“One week in, we let the story begin/ We’re goin’ out on our first date”) or tapping into multiple layers of meaning (“We talk for hours and hours about the sweet and the sour…”)

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There have been some clunkers in his catalog, for sure: references to Shrek and a—hole bleaching have provided certain songs with needless blemishes, yes. But through all his genre-hopping and unorthodox wordplay, at the very least he can say he’s forged a style that’s entirely his own. His mass appeal may make him “generic” by definition, but his sound is his: Even the successors to his guy-with-a-guitar pop-rock mantle – Shawn Mendes, Lewis Capaldi, Noah Kahan — haven’t once gone near the playful experimentation Sheeran cut his teeth on, instead favoring safer, more traditional songwriting structures.

It’s also notable that Sheeran has never been dishonest about where his scattered musical influences came from, nor has he ever lazily copied anyone else. He’s always stated his love for figures like Damien Rice, Eminem and Eric Clapton, and he worked exclusively with grime artists on the self-released 2011 EP No. 5 Collaborations Project. And at a time where any male artist with his tastes would’ve earned far more cool points by positioning himself as an aloof rock star in the vein of Oasis or Arctic Monkeys, he instead fully, authentically embraced the world of pop and its leaders, teaming up with Taylor Swift on “Everything Has Changed” in 2013 and penning hits for Biebs and 1D (2012’s “Little Things” and 2015’s “Love Yourself,” respectively.)

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All of this to say, maybe Sheeran’s songs aren’t just soulless composites of popular genres designed to be as widely played as possible, but the natural blended output of a guy with a genuine love and appreciation for all the styles he employs. He also happens to be very strategic when assembling those puzzle pieces in a song, preternaturally sensitive to which elements are most likely to make for a successful hit – a personal goal he’s long been transparent about chasing. (“I have a data sheet emailed to me every week,” he told GQ with a wink in 2017. “My benchmark for the second album was Coldplay. This album it’s Springsteen.”)

The spectrum of his sound runs parallel to how much he does or doesn’t tailor songs for commercial success. On one end there’s the smoke-blowing songs like 2011’s “You Need Me, I Don’t Need You” and 2017’s “New Man” where he fully indulges his love for loose, slightly silly rapping. Though they might become fan classics, they’re the least programmed to become global hits — he’s just having some fun. On the other end are his sweeping romantic ballads like “Thinking Out Loud,” “Photograph” and “Perfect,” which are maniacally constructed for decades of play at weddings and high school dances. But of these, ask yourself: if not Sheeran, who else is up to the task of pumping out this generation’s deck of timeless sappy slow-dance songs?

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In the middle is everything else, the so-called homogenized, post-genre songs that have a little something for everybody. There are several different outcomes songwriters pursue when writing music, and consequently, there are just as many measures of that music’s quality. None are necessarily right or wrong. Swift’s goal is to tell personal stories through her songs. Pitbull wants people to dance. Adele aims to pack an emotional punch. And each of these objectives requires a great deal of craftsmanship when putting pen to paper. Even if Sheeran’s desire has been to write songs surgically stitched together for easy listening, does he really forfeit any recognition for being one of his generation’s most innovative songwriters just because his music is created with algorithmic precision?

When one of his songs ultimately gets stuck in your head for weeks, you might curse his formula as being that of an evil genius. But the key word here is still “genius.”

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. We’ve already named our Honorable Mentions and our No. 25 star, and now we remember the century in Ed Sheeran — who went from coffee shops to stadiums without ever changing his fundamental singer-songwriter identity.

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A single person, playing the guitar alone on stage in the middle of a stadium. It’s a fantasy — being an artist whose music and lyrics are simply so undeniable, so unifying, that they leap from the meekest clubs to the most gargantuan venues in the world! — that countless singer-songwriters from all walks of life have attempted to strum into reality over the past 25 years, and almost every single one has come up short. It’s the wrong instrument for this century, really: modern pop does not function like it did back when rock ’n roll was the dominant sound, so this Greatest Pop Stars list does not include a slew of six-string-toting chart-toppers.

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With that in mind, the scale of Ed Sheeran’s 21st century success is even more impressive. In a pop age where singer-songwriters generally bump against their commercial ceiling relatively early in their evolution, this red-headed kid from Halifax kept soaring higher and higher, eventually reaching a space where his longevity, global appeal, influence and multi-quadrant hits allowed him to stand alone. He used to be a teen busking on the streets of London; now, Sheeran often finds himself in the center of 80,000 people, an acoustic strapped to his shoulder, no one and nothing else in his vicinity. And considering everything he’s done, he doesn’t even look that out of place.

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Unlike hitmakers such as John Mayer, Jason Mraz and Gavin DeGraw — singer-songwriters who burst onto the scene in the 2000s with flashy, radio-friendly pop singles — Sheeran began his journey into the spotlight with a quiet, unassuming breakthrough hit. Following years of independent releases in between street performances and open-mic nights across the U.K., Sheeran chose “The A Team,” a pleading folk ballad about a sex worker addicted to drugs, as his debut single in 2011 – betting on its juxtaposition of finger-picked melodies and a soothing vocal tone with dark subject matter and stripped-down production.

The bet paid off: In the heart of the EDM-fueled, turbo-pop assault at the top of the Billboard Hot 100, the minimalist sing-along of “The A Team” counteracted the spastic movement of concurrent megapop hits by LMFAO and Pitbull. There had been no shortage of hushed, bleeding-heart singer-songwriter fare that had found its way to adult pop listeners prior to “The A Team” taking off, but Sheeran’s debut was a touch smarter (“A Team” refers to the “Class A drugs” that the song’s subject has taken), more sincere (the way Sheeran warbles “She don’t wanna go-o-o-o outside, tonight” as a major emotional payoff), and altogether more striking than the soundalike songs around it, climbing to No. 3 in Sheeran’s native U.K. and to No. 16 on the Billboard Hot 100. 

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Beyond its chart peaks, “The A Team” introduced Sheeran as an early-twenties troubadour worth investing in long-term. He played the song on late-night talk shows, and later at the Grammys, where it was nominated for song of the year. Sheeran’s debut studio album, +, arrived a few months later in 2011, scoring a respectable No. 5 debut on the Billboard 200. And while third single “Lego House” replicated the gentle guitar-pop formula of “The A Team” (with a Rupert Grint-starring music video, as a play on the Harry Potter actor’s physical resemblance to Sheeran), in between, “You Need Me, I Don’t Need You” shook up Sheeran’s image as a hip-hop-adjacent music industry shrug-off, with the singer-songwriter rapping over drum loops, guitar and piano. The song never reached the Hot 100, but became a live staple and fan favorite; more importantly, “You Need Me” expanded expectations for what an Ed Sheeran song could sound like as his voice was reaching wider audiences.

Soon enough, those wider audiences would include Taylor Swift — a country superstar yet to fully cross over to pop in the early 2010s. Swift tapped Sheeran for the Red duet “Everything Has Changed,” which became a top 40 Hot 100 hit as one of the album’s later singles, then brought him on the road as the opening act on the Red arena tour. Swift’s co-sign was and remains a crucial stamp of approval for aspiring artists, but she went above and beyond as an early Sheeran supporter; the two remain close friends and collaborators more than a decade later, having recently re-recorded “Everything Has Changed” for Swift’s mega-selling Red (Taylor’s Version).

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By the time Sheeran’s stint on the Red Tour wrapped up in September 2013, he was a star in his own right, headlining Madison Square Garden for the first time that fall and picking up a best new artist Grammy nomination. The collaborators on his next album, 2014’s x, demonstrated the glow-up of the busker turned arena headliner: lead single “Sing” was produced by Pharrell Williams, working the same rhythmic magic that he applied to Justin Timberlake’s debut solo single “Like I Love You,” and follow-up single “Don’t” was helmed by the unlikely generation-separated super-producer duo of Rick Rubin and Benny Blanco.

To this end, x functioned exactly like its titular math symbol would suggest, taking Sheeran’s sonic blueprint and increasing its scope and sound: “Sing” was a rhythmic pop cut that brought Ed’s storytelling to the club for the first time, while “Don’t” was a jilted-lover lament (about a fling with a fellow pop star, rumored to be Ellie Goulding) that diced up sighing harmonies among rapped verses. Yet “Thinking Out Loud,” the blue-eyed soul romantic ballad, was bigger than either of them, heightening Sheeran’s earnestness and sentimentality to wedding first-dance proportions. “Thinking” reached No. 2 on the Hot 100, stuck for eight weeks behind Mark Ronson and Bruno Mars’ “Uptown Funk!” — but winning song of the year at the 2016 Grammys, after performing the song alongside John Mayer, Questlove and Herbie Hancock at the 2015 ceremony, made for a nice consolation prize.

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As the wins kept accumulating for Sheeran in the mid-2010s, he started scoring hits that sounded like Ed Sheeran songs but came under the names of other artists. “Love Yourself,” an acoustic kiss-off performed by Justin Bieber, became a downtempo smash from his Purpose album by essentially replicating the Sheeran songwriting formula and serving it as a change-up from Bieber’s trop-pop hits “What Do You Mean” and “Sorry.” In the years leading up to “Love Yourself,” Sheeran also co-penned songs for artists like One Direction and Jessie Ware, but Bieber’s hit (which topped the Year-End Hot 100 in 2016) was an inflection point for the songwriting calls he started answering, and was followed by top 10 hits like Major Lazer’s “Cold Water,” Benny Blanco’s “Eastside” and Liam Payne’s “Strip That Down.” More often than that, the songs co-written by Sheeran smacked of his tone and melodic instincts, a superstar bending other perspectives and sounds toward his own.

Meanwhile, he also established himself as a must-see live performer. The x Tour was Sheeran’s first arena headlining trek, and he successfully translated his long-running stage setup — no backing band, no glitz or glamour, just a collection of pedal loops that allow him to re-create the sonic worlds of his songs on his own — for tens of thousands of ticket buyers. Whether perceived as a gimmick or an act of live-show wizardry, Sheeran’s touring approach gave him an identity in a crowded market as he accrued more hits to play for bigger audiences; no matter who else was out on the road, they weren’t going to put on a show quite like Ed’s.

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If x was the album that elevated Sheeran to pop’s arena class, its follow-up, 2017’s ÷, was the project that made him a no-doubt superstar. That’s mostly thanks to “Shape of You,” the gargantuan lead single that will likely stand as the biggest hit of Sheeran’s career: a tropical house cocktail with a propulsive marimba line, playful falsetto and vocal chants that inject some drama into Sheeran’s tipsy flirtations, the song spent a whopping 12 weeks atop the Hot 100, gobbled up millions of radio spins and billions of streams, and finished 2017 as the biggest song of the year. If Sheeran’s career prior to that moment consisted of revving up his pop bonafides, “Shape of You” slammed down the gas, as a fully inescapable smash that is now officially one of the 10 biggest songs of the Hot 100 era.

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Of course, the success of ÷ wasn’t limited to one song: “Castle on the Hill,” the racing rock single that Sheeran released on the same day as “Shape of You,” became a top 10 hit as well, and stands as one of his most emotionally resonant radio favorites. The Irish folk riff “Galway Girl” never reached the chart heights of its fellow singles on the track list, but quickly became a beloved fan track, and its streams have surpassed the 10-figure mark. And “Perfect,” another wedding-ready waltz in the mode of “Thinking Out Loud,” received a remix featuring none other than Beyoncé that December, which helped the single power to the top of the Hot 100. Toss in “End Game,” Swift’s Reputation track featuring Sheeran and Future, and Ed ended the biggest year of his career as an unquestioned A-lister, capable of leading hits on his own and holding his own alongside fellow superstars on blockbuster collaborations. (In 2019, Billboard named Sheeran the Greatest Pop Star of 2017.)

Topping that 2017 commercial apex was almost impossible to imagine — and to his credit, Sheeran didn’t really try to. His next full-length was 2019’s No. 6 Collaborations Project, a collection of household-name team-ups that was inspired by one of Sheeran’s pre-fame projects. The left turn tempered the sky-high commercial expectations of the proper ÷ follow-up, although “I Don’t Care,” the album’s dancehall-adjacent duet with Justin Bieber, still became one of the biggest pop hits of the year, reaching No. 2 on the Hot 100. Also featuring Travis Scott, Cardi B, Chris Stapleton and Bruno Mars, among many others, No. 6 became another No. 1 album for Sheeran, in the same month that his two-year-plus world tour in support of ÷ finally wrapped up, as the biggest of all time to that point; he largely took the next year off at the COVID-19 pandemic raged, and became a father in August 2020.

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Sheeran’s next proper solo album, 2021’s =, powered him into his second decade as a star, with the singles “Bad Habits” and “Shivers” both riding uptempo pop productions and major hooks toward comfortable stays inside the top 10 of the Hot 100 chart. Swift appeared on a remix of the album’s “The Joker and the Queen,” and Lil Baby stopped by a new version of “2Step”; outside of =, Sheeran swung by a reworked version of “Peru,” from Nigerian star Fireboy DML, to notch another global hit that recalled some of the cross-genre pollination from No. 6 Collaborations Project. After that, a hard pivot: 2023’s – album marked a downbeat reflection on personal tragedies, including the death of Sheeran’s close friend and complications with his wife’s pregnancy, that was primarily produced by Aaron Dessner, who had helped Swift enter indie-folk terrain on Folklore and Evermore three years earlier. Both – and its surprise follow-up/counterpart, Autumn Variations, were too mournful to spawn any hit singles, as Sheeran seemingly issued both projects more for his own peace of mind than for radio gains.

But that’s the good thing about graduating to no-brainer stadium status: Sheeran can easily weather a commercial lull because he’s collected so many hits, and established his brand over the course of a decade-plus, while remaining a road warrior and onstage force. He’s been adjacent to the biggest artists of the 21st century while sneakily out-streaming a lot of them; just take a peek at Sheeran’s Spotify page, and try to count up how many of his songs have crossed the one billion mark. And while Ed has never been the toast of tastemakers, he has unquestionably written songs that are built to last — new wedding-reception staples and tried-and-true pop playlist mainstays — while also influencing the next generation of singer-songwriters, who have their sights set on the biggest crowds imaginable.

Ed Sheeran has transcended every pop trend, succeeded in a variety of styles, and made his voice a familiar sound in every context of modern pop music. He’s still enormous, and probably will be for a long, long time. Not bad for a guy with an acoustic guitar and loop pedal.

Read more about the Greatest Pop Stars of the 21st Century here and check back on Tuesday when our No. 23 artist is revealed!

With the first quarter of the 21st century coming to an end, Billboard has been looking back on the 25 Greatest Pop Stars of the Past 25 Years. Below, we take a deeper look into the peak of our No. 25 pop star, Katy Perry, and how her sophomore major-label album defined a moment in pop and music industry history, even as that moment was coming to its close.
When Katy Perry’s single “Last Friday Night (T.G.I.F.)” hit No. 1 on the Hot 100 in August 2011, it made Billboard history: For the first time since Michael Jackson, an artist had topped the chart with five different songs from the same album. For 14 months, Perry and her second major-label album, Teenage Dream, had dominated the Hot 100, with “California Gurls,” then “Teenage Dream,” then “Firework,” then “E.T.”; the star and her five ubiquitous singles held the Hot 100’s top slot for a combined 19 weeks over that period. 

With Max Martin, Dr. Luke, Stargate, and a still-rising young gun named Benny Blanco in her corner, Perry constructed a bulletproof, era-defining pop album – one that topped the Billboard 200 and is today certified diamond by the RIAA. But while Teenage Dream marked Perry’s transition into full-fledged pop superstar and heralded a decade where she’d top the Hot 100 three more times and headline the Super Bowl halftime show, it also represented a broader sea change in the music business and the way audiences consumed music. 

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 “Maybe CDs will be extinct next time I put out [an] album… so I wanted to go out with a bang for people to remember this,” Perry said when she revealed Teenage Dream‘s pin-up-inspired artwork a few weeks before the album’s August 2010 release. Sure enough, by the time she released her next album a little over three years later, Spotify and streaming had become a cornerstone of the music business, YouTube’s viewership had multiplied several times over and Instagram had gone from a soon-to-be-released photo app to a key component of Facebook’s social media empire. The internet had changed – and so had the way listeners digested pop music. 

Incidental prescience aside, this was likely not Perry’s headspace in 2010. Even as album sales at the industry’s top tier dwindled from their turn-of-the-century peak, Perry and Capitol Records ran back the tested record release playbook: two titanic pre-album singles to lead a savvy marketing campaign and juice excitement, followed by four smartly deployed singles after the project hit record stores (the sixth, “The One That Got Away,” didn’t top the Hot 100, but was no chart slouch, peaking at No. 3 more than 16 months after Teenage Dream‘s release).  

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In retrospect, the music is similarly transitional. Teenage Dream epitomizes post-recession, Obama-era pop: big, brash synths and the embrace of EDM; unabashed tonight’s-the-night party vibes; and a few questionable lyrics here and there that wouldn’t make a major pop release today. As much as Teenage Dream was Perry’s accomplishment, it was also Max Martin’s, who co-produced four of its five No. 1s; despite his successful ’00s, today the album clearly marks the start of his ’10s renaissance. In 2010 and 2011, he notched two other No. 1s (with Pink and Britney Spears) along with other massive hits (Taio Cruz’s “Dynamite,” Usher’s “DJ Got Us Fallin’ In Love”), and the next few years would bring an onslaught of Martin-produced hits by Taylor Swift, Ariana Grande, The Weeknd and others. 

Perry’s 2008 singles “I Kissed a Girl” and “Hot N Cold” were the prototype for her Teenage Dream era, in large part because – like “Teenage Dream and “California Gurls” – their credits include the triumvirate of Martin, Dr. Luke and Benny Blanco. Luke and Blanco defined this era, through their work with Kesha and a slew of other artists. But where Blanco is an essential pop throughline from the late ’00s to the ’10s – when he helped craft ubiquitous hits by the likes of Justin Bieber and Ed Sheeran – Luke soon became a non-factor, marginalized by the allegations of misconduct against him, although he’d go onto to reignite his career through hits with artists like Doja Cat and Nicki Minaj. (Dr. Luke denied the allegations, from former collaborator Kesha, and countersued for defamation; the extended legal battle ended in 2023 with the two parties settling the countersuit out of court.) Stargate, which co-produced “Firework,” along with several other key singles from the era, also soon faded in influence as the musical landscape of the ’10s settled into place. 

Katy Perry

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But far more than defining the era’s aesthetic, Teenage Dream also captured a music business in transition. For decades, pop megablockbusters enjoyed protracted rollouts where every single mattered – and while Perry worked each of the album’s singles to the hilt, like an ‘80s superstar might’ve, she also applied a distinctly modern sensibility. For instance, on singles Nos. 4 and 5 she added Kanye West and Missy Elliott (to “E.T.” and “Last Friday Night,” respectively), extending the lifespans and commercial ceilings of those singles along the way. Though some industry onlookers cried foul at the time, such chart-boosting maneuvers would soon become commonplace for big pop artists. 

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Streaming afforded a certain flexibility to artists – by the mid-’10s, the surprise release became the trendy strategy for superstars – and reduced the need for major singles to extend an album’s longevity. Take Taylor Swift’s The Tortured Poets Department, which continues to dominate the Billboard 200 despite lacking singles with similar commercial legs. (The other side of that coin: Had Perry’s peak coincided with the streaming age, it’s easy to imagine a new album from her charting all or most of its tracks on the Hot 100.) Streaming has fundamentally reoriented how singles interact with the broader pop world – potentially at the expense of the year-plus cycles that made it feel, a little, like a pop artist had truly taken over the world. 

Perry’s reign in 2010 and 2011 was among the last of its kind, as the sun set on the era where fourth, fifth and even sixth singles still really mattered. And with every passing year – even as Hot 100 records fall thanks to idiosyncrasies of the streaming economy and modern chart tabulation – her record of five Hot 100 No. 1s from a single album seems increasingly untouchable, like certain gaudy stats from baseball’s dead-ball era. No artist, not even Swift, has even notched four Hot 100 No. 1s from a project since. Still, there’s a reason why even under the old paradigm, Perry was only the second artist to achieve the feat: She had the classic singles to back it up. 

In 2019, Billboard‘s staff revealed its picks for the greatest pop star of every year dating back to 1981 (the first year of MTV, essentially the birth of the modern pop era), with essays making the case for each as the biggest, brightest and most important star in their solar system that calendar year. For the last few years, we’ve also counted down our picks for the 10 greatest pop stars of the 12-month period, with each getting their own year-in-review tribute from one of our staffers. (Our picks for the No. 1 Greatest Pop Star of the Year this decade have included BTS, Bad Bunny and Taylor Swift.)

But with the quarter-century mark coming up, we decided it was a good time to zoom out a little bit on the whole last 25 years in pop stardom. And so this week, we begin our countdown of the 25 Greatest Pop Stars of the 21st Century: a list attempting to take stock of the pop stars who have been most important and most impactful in the U.S. over that timespan. We will be unveiling our list over the course of the next four months, unveiling one or two artists a week, along with our usual essays commemorating each artist — as well as additional articles focusing on different aspects of their careers and rounding up their chart achievements, and regular podcast and video discussions of our chosen stars’ careers and legacies. We hope it will all serve to properly celebrate the 25 artists who have most defined the pop music and pop culture of the first 25% of this century, and to help provide an accurate snapshot of how the sound, look and overall meaning of pop superstardom have evolved over that period.

First, however — we must acknowledge that 25 is simply nowhere near a big-enough number to properly acknowledge all the pop stars who have dominated the charts and moved the culture since Y2K. So with that in mind, we’re starting off our rollout of this project with a quick unranked list of our Honorable Mention picks for the best of the rest: the 25 pop stars who were great enough to get strong consideration for our top 25, but ultimately just didn’t quite have either the stats, the impact, the longevity or the volume to elbow their way into our main list. We love ’em all just the same, and we couldn’t kick off this project in earnest without giving them their proper due first.

And we must also issue our obligatory reminder that unlike with our Year-End Charts, these Greatest Pop Stars are NOT mathematically determined by stats like chart position, streams or sales numbers. Those play a big part in our final rankings, of course — you can’t be one of the greatest pop stars of the century without great pop hits and great pop albums — but so do things like music videos, live performances and social media presence, and more intangible factors like cultural importance, industry influence and overall omnipresence. (And we’re measuring this over all 25 years of this century so far, so if you were only heard from at the beginning or the end of that period — or only had one or two big songs, albums or eras — that’s gonna significantly hinder your ranking here as well.)

Here are our 25 picks, presented alphabetically, for the closest-but-not-quite pop stars — the Nos. 26-50 Greatest Pop Stars of the 21st Century, essentially — and check back throughout the next few months as we count down our top 25, and officially name our Greatest Pop Star of the 21st Century this autumn.

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