Greatest Pop Stars of 21st Century
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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.
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 done our Honorable Mentions, and now at No. 25, we remember the century in Katy Perry — whose dizzying, era-defining early-’10s peak still burns bright in the minds of pop fans, even as it gets farther away.
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For anyone who lived through her commercial peak, Katy Perry will always be one of the names most synonymous with pop music. There’s a lot of reasons for that, but perhaps the biggest is that few performers of the last 25 years have felt as committed to maxing out top 40 superstardom at its biggest, brightest and best: When Katy Perry ruled the mainstream at the turn of the 2010s, it felt like she was wringing every ounce of potential from her albums, singles, videos, live performances, TV appearances, fashion and branding choices and general public persona. It was pop as the most legendary icons of early MTV once envisioned it – and perhaps unsurprisingly, it matched their success in ways no other artist this century has managed.
Few would have imagined that fate for Katy Perry when she initially emerged – first briefly in the early ‘00s as Katy Hudson, contemporary Christian artist, and then rebranded as snotty Warped Tour singer-songwriter Katy Perry later in the decade. “Ur So Gay,” the metrosexual-taunting title track to her first Perry-era EP release, suggested great promise for word-of-mouth cult success, but seemed too cheeky, too edgy and too problematic for top 40 success. At the time, the mainstream had been dominated for years by hip-hop, Auto-Tune and post-American Idol pop-rock seriousness; there didn’t seem to be too much of an opening for the kind of technicolor, attitude-driven turbo-pop Perry was bringing to the table.
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But whatever opening was there, Katy Perry’s next song was forceful enough to guarantee that it pushed its way through. The bicurious “I Kissed a Girl” arrived sounding and feeling like an absolute juggernaut, a barnstorming electro-rock singalong with writing credits from pop royalty Max Martin and Cathy Dennis and cutting-edge production from Martin’s long-time collaborator Lukasz “Dr. Luke” Gottwald and Luke’s protege Benny Blanco. Rather than softening Perry’s edges, the song just made them sharper: “Girl” was louder, brasher and even more divisive than “Gay,” drawing criticism both from moral-outrage conservative groups offended at the song’s homosexual flirtations and from LGBTQ critics annoyed by the song’s perceived queerbaiting.
Ultimately, the noise around “Girl” just ended up pumping up the volume of the song itself, which blazed its way to No. 1 on the Billboard Hot 100 in July 2008. By then, parent album One of the Boys had been released, with the major-label debut set entering the Billboard 200’s top 10 and spawning another three hit singles. Two of those were Hot 100 top 10s: the bubbly relationship eye-roller “Hot n Cold,” which was arguably both her rudest and most unstoppable pop-rock blast yet, and the widescreen morning-after anthem “Waking Up in Vegas,” a less-bratty but still delectably post-hedonistic story song. In between them was the more straightforward ballad “Thinking of You,” her first single that sounded like it could’ve been done by one of her then-top 40 peers; the song tapped out at No. 29 on the Hot 100, suggesting audiences preferred Katy Perry at her Katy Perriest.
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That notion would be confirmed by Perry’s sophomore set, a one-woman home-run derby that ultimately made the tremendous success of her One of the Boys era look like a couple of practice swings. Teenage Dream was first trumpeted in May 2010 with the arrival of the irresistible “California Gurls,” a Jay-Z-and-Alicia-Keys-responding, Beach Boys-and-Big-Star-quoting love letter to the Golden Coast, blessed by no less an esteemed West Side representative than Snoop Dogg. The song was every bit as big and bursting as Perry’s One of the Boys singles – and with enough PG-13 content to keep it from getting too bubblegum – but without any of the sneering or snarkiness that punctuated those hits, ensuring nothing stood in the way of its summer dominance. Meanwhile, the song’s candyland fantasia of a music video made iconic images out of a dramatically wigged Perry laying nude on a cloud and shooting whipped cream cans from her breasts, ensuring she was just as unavoidable on MTV and YouTube as she was on the airwaves.
That song shot to No. 1 on the Hot 100 in June, and by the time of Teenage Dream’s August release, its follow-up – the album’s title track, an immediately immortal young-love anthem as daydreamy as “Love Story” and as fist-pumping as “Livin’ on a Prayer” – was also on its way there. Teenage Dream itself debuted atop the Billboard 200, and went on to blanket pop culture for the entire next year and a half, with a jaw-dropping three more Hot 100 No. 1 hits to follow: the inspirational electro-pop floor-filler “Firework,” the beat-heavy out-of-this-world love song “E.T.” (with a guest verse from Ye, then Kanye West, on the single edit) and another winking how-wasted-were-we remembrance in “Last Friday Night (T.G.I.F.).”
Katy Perry
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Katy Perry
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With the fifth No. 1 off Teenage Dream, the album famously made chart history, as just the second set (after Michael Jackson’s 1987 blockbuster Bad) to ever spawn five Hot 100 No. 1 hits. The achievement capped one of the most successful album rollouts in pop music history, with each single essentially becoming its own mini-universe, given its own sound, look, aesthetic and narrative different from the other four. It also showed Perry and her team to be at the forefront of finding ways to build excitement and consumption for late-cycle singles in the digital age; adding Ye to the single release of “E.T.” and Missy Elliott to the remix of “Last Friday Night” helped get those songs to No. 1 on the Hot 100 years before adding after-the-fact A-listers became standard practice for big pop singles.
And Perry’s ubiquity at the time went far beyond the Billboard record books: For about two years at the beginning of the decade, she was absolutely unavoidable throughout pop culture. She appeared in Proactiv commercials and on Sesame Street, she walked red carpets with star comedian Russell Brand (her then-husband) and sat next to fellow pop megastar Rihanna at award shows, she hosted SNL, she kissed a Smurf and she liked it. She traversed the globe on her kaleidoscopic California Dreams tour, racking up nearly $60 million in box office for just her second headlining trek, according to Billboard Boxscore. She racked up additional honors across the pop culture spectrum, from video of the year (for “Firework”) at the MTV Video Music Awards to most beautiful woman in the world on the Maxim Hot 100. And oh yeah, she also released a Complete Confection deluxe edition of Teenage Dream that spawned another No. 1 in the defiant shout-along “Part of Me” and nearly another still in the No. 2-peaking post-breakup ballad “Wide Awake.”
Katy Perry
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More than that, Katy Perry also helped define the sound and look of a particularly fertile and oft-romanticized period in pop music history. The early 2010s represented something of a golden age for pop enthusiasts, one defined by epochal stars like Rihanna, Lady Gaga, Beyoncé, Taylor Swift and even a resurgent Britney Spears, as well as massive radio hitmakers like Kesha, Pitbull, Flo Rida, LMFAO and the Black Eyed Peas. EDM, Young Money, Glee, Adele – it was all happening at once. And the most omnipresent, most dead-center star of the era was almost certainly Katy Perry. It was her turbo-charged pop and kitchen-sink visual aesthetic that set the tone for the era of massive pop songs and even bigger personalities, and her collaborators (Martin, Luke and Blanco, as well as “Firework” producers Stargate) who would create the default sonic palate for the top 40 of the time.
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While Perry became more central to pop music in the early 2010s than anyone would have guessed possible of her years earlier, her time at top 40’s core would also be briefer than many would have predicted once she arrived. She spent one more album as a no-doubt superstar: 2013’s Prism, which topped the Billboard 200 and spawned a pair of massive, Hot 100-besting smashes in the motivational anthem “Roar” and the trappy, Juicy J-featuring seduction jam “Dark Horse.” (Both songs would make the setlist when she took a career-peak victory lap in February 2015, as she headlined halftime at Super Bowl XLIX, in what was at the time the most watched halftime show in Super Bowl history.) Despite being a big win overall, the album didn’t quite have the legs of Teenage Dream, and later singles “Birthday” and “This Is How We Do” would end up missing the top 10 altogether.
Subsequent albums fared no better. Witness became her third straight No. 1 LP upon its 2017 release, but its release was marred by an uncharacteristically messy and confusing rollout – as Perry tried to pivot to a more conscientious, “purposeful” approach to pop – and it only spawned a single top 40 hit, with the No. 4-peaking, Skip Marley-featuring lead single “Chained to the Rhythm.” That song, which was released in the aftermath of Donald Trump’s 2016 presidential election win (after Perry had been one of pop’s most vocal and visible Hillary Clinton supporters), was indicative of the difficulty she had fitting into the back half of the 2010s – a pop scene more defined by light, swaying trop-pop and muddy, downtempo SoundCloud rap than the kind of frothy pop-rock missiles she’d made her name on. When 2020’s Smile became the first Katy Perry album not to produce a top 10 hit, it suggested that her time at popular music’s forefront had perhaps come to an end.
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However, even as her presence in the pop mainstream became less overwhelming, Perry hardly ever vanished. She joined American Idol as a judge in 2018, helping the show remain a ratings draw for seven seasons. She began the highly successful Las Vegas residency Play in 2021, cementing herself as one of pop’s pre-eminent legacy performers. She also scored a number of hit collaborations, taking hook duties on superproducer Calvin Harris’ “Feels,” teaming up with reggaetón star Daddy Yankee on the bilingual banger “Con Calma” and enlisting EDM hitmaker Zedd to co-produce the Smile lead single “Never Really Over.” None of them quite reached the four-quadrant smash status that Perry routinely managed in the Obama years, but all were fairly well received – with “Over” in particular remaining something of a fan favorite and should’ve-been-bigger pet cause among diehard KatyKats.
`In 2024, Perry has parted ways with Idol and wrapped her Vegas residency, as she prepares for a big career comeback with September’s 143 album. That’s gotten off to a somewhat rocky start with lead single “Woman’s World,” which only reached No. 63 on the Hot 100 and drew mostly negative reviews – with many critiques from fans and critics focusing on the jarring nature of the women’s empowerment anthem being co-produced by Dr. Luke, who was sued by Kesha in 2014 over allegations that he had been abusive in their professional and personal relationship. (Dr. Luke denied the allegations and countersued for defamation; the long legal battle ended in 2023 with the two parties settling the countersuit out of court.)
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But even if Katy Perry’s songs are no longer omnipresent in today’s pop, her fingerprints still are. You can feel her in the eye-popping costumes and theatrically vivid world-building of Chappell Roan and the sticky sweet and slightly naughty hooks of Sabrina Carpenter. And even the backlash to “Women’s World” is indicative of Perry’s enduring level of stardom – the song dominated headlines for a week, as folks couldn’t resist weighing in on it one way or the other – and the fact that so many fans are still rooting for her. At her apex, Katy Perry was as proud and formidable a pop purveyor as we’ve seen this century, and she will forever be associated with the highest highs of that fondly remembered era: a teenage dream that countless millennial and Gen Z pop fans will never totally wake up from.
Read more about the Greatest Pop Stars of the 21st Century here and check back on Thursday when our No. 24 artist is revealed!
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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