Over the next four months, Billboard will be unveiling our picks for the 25 most important and impactful pop stars of the last 25 years. But first: the best of the rest.

The Greatest Pop Stars of the 21st CenturyBillboard

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.

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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.

50 CENT

50 Cent
Photo : Gregory Bojorquez/Getty Images

His 21st Century in Pop: Perhaps no rapper this century had a breakout more magnificent than the artist born Curtis Jackson, as his 2003 debut LP Get Rich or Die Tryin‘ arrived on the back of an avalanche of mixtape and media hype (and one of the greatest lead singles in hip-hop history) and played like an already-minted greatest hits album. His mercenary approach to rap led to absolutely stratospheric commercial heights — including well over a million in first-week sales for sophomore set The Massacre — and between his instantly iconic album covers, unavoidable music videos and increasing visibility in film and television, chances are even your grandmother could recognize him by his pecs alone.

Why Not Top 25? After losing a much-publicized first-week sales showdown with Ye (then Kanye West) in 2007, the bottom fell out for 50 Cent surprisingly quickly — he’s yet to score a Hot 100 top 10 hit as a lead artist or a Billboard 200 No. 1 album since, and new releases became more scattershot as he shifted focus to his acting career and business investments.

ALICIA KEYS

Alicia Keys
Photo : Anthony Barboza/Getty Images

Her 21st Century in Pop: The American Idol era desperately needed an Alicia Keys, a soul singer-songwriter and piano prodigy whose pipes were as immaculate as both her pen and her general credibility. It’s hard to imagine the first half of the 2000s without her Songs in A Minor and The Diary of Alicia Keys and their respective show-stopping singles; subsequent albums squeezed out singalongs for the heavy-hearted for well into the next decade, as she upped her always-welcome presence in film and TV. As you read this, chances are some future spotlight-stealer is currently auditioning for their first major look with “If I Ain’t Got You.”

Why Not Top 25? Rarely totally absent from the mainstream over the past 20 years, Keys’ time as a pop superstar was nonetheless mostly limited to her first three albums, and she hasn’t had a real hit single since 2012.

BILLIE EILISH

Billie Eilish
Photo : Mason Poole

Her 21st Century in Pop: The first artist born in the 21st century to score a Hot 100 No. 1 hit could not have felt a more appropriate paragon of Gen Z superstardom: Billie Eilish was trend-defying, she was both incredibly dark and incredibly silly, and she kept her closest collaborator limited to her immediate family – but she was also undeniably, massively pop. In the five years since debut When We All Fall Asleep, Where Do We Go simultaneously made her a chart-topper, a style and music video icon and a Grammy darling, Eilish has proven worthy of her generation-leader status by evolving rapidly as an artist while maintaining her ability to create era-defining smashes. No other artist could go from “Bad Guy” to “My Future” to “Lunch” without ever having to leave the top 10.

Why Not Top 25? Simply a matter of volume: If her rise had started a couple years earlier or this period ended a couple years later, it’d be almost impossible to keep her out.

CARDI B

Cardi B
Photo : Brian Ziff

Her 21st Century in Pop: Set aside the long-delayed sophomore album — as the wait for the follow-up to her spectacular 2018 debut Invasion of Privacy continues, Cardi B’s sustained commercial power and multi-platform superstardom has only become more impressive. In 2017, “Bodak Yellow” transformed Cardi from a reality-TV fixture to a chart-topping rap phenom; Invasion quickly capitalized on the single’s success, while also sending rising Spanish-language stars Bad Bunny and J Balvin to the top of the Hot 100 with “I Like It.” Over the next half-decade, Cardi kept cranking out hits that either crossed over to pop radio (like “Girls Like You” with Maroon 5) or exploded across hip-hop culture (like “WAP” with Megan Thee Stallion), while also dabbling in Hollywood projects and brand deals. Now, Cardi is one of the most influential female rappers ever, and one of the most bankable hit-makers across all of hip-hop, making money moves while the rest of the world waits for her next big one.

Why Not Top 25?: Tough to crack the quarter-century list when your mainstream breakthrough came two-thirds of the way through those 25 years. And even though Cardi kept scoring hits following the Invasion of Privacy era, some of those hits — “Money,” “Up,” “Enough (Miami)” — might have enjoyed longer chart runs had they been tethered to a proper full-length.

CARRIE UNDERWOOD

Carrie Underwood
Photo : Jeff Johnson

Her 21st Century in Pop: One of the two most recognizable American Idol alums in popular music, Carrie Underwood has been one of country music’s defining voices since she first topped the Hot 100 with Idol victory single “Inside Your Heaven” back in 2005. In the years that followed, Underwood scored some of the genre’s biggest crossover hits in “Jesus, Take the Wheel” and “Before He Cheats,” and earned four Billboard 200 chart-toppers. Her powerful belts and thunderous performances have also made her live shows bustling attractions; in addition to her most recent arena tour, she’s extended her blockbuster Las Vegas residency all the way into 2025. Not only has the eight-time Grammy winner been inducted into the Grand Ole Opry and the Hall of Fame in her home state of Oklahoma, but she’s also topped the Christian Albums chart twice (with 2020’s My Gift and 2021’s My Savior), and is one of the few musicians who can say they’ve been synonymous with Sunday Night Football.

Why Not Top 25: While she was a consistent seller in the late ’00s and early ’10s, her recent studio efforts haven’t made as much of a commercial impact, and her crossover success has been fairly limited for the last decade.

CHRIS BROWN

Chris Brown
Photo : Samir Hussein/WireImage

His 21st Century in Pop: In the wake of Usher’s mid-’00s mega-dominance, Chris Brown emerged as the next man up in the timeless triple-threat model of pop&B stardom. He topped the Hot 100 right away with “Run It!” and quickly proved he had the songs to match the skills; when he performed with Rihanna at the 2007 VMAs it seemed like pop had found its reigning power couple for many years to come. That relationship of course ended horrifically just a couple years later, with Brown’s abuse permanently tainting both his image and his music, and further violent outbursts would ensure he never recaptured the innocent magic of his early years. But he pivoted to a more caddish public image and never really stopped having hits, as his fans remained loyal, his music evolved with the times, and no younger version of himself ever rose up to replace him.

Why Not Top 25? Even as he rebounded quickly commercially, Brown understandably remained a highly divisive figure in the pop world, with just those first few years remaining treasured memories for (nearly) all.

CHRISTINA AGUILERA

Christina Aguilera
Photo : Getty Images

Her 21st Century in Pop: Christina Aguilera actually had the first new Hot 100 No. 1 hit of the 21st century, with the second single off her debut album, as “What a Girl Wants” followed “Genie in a Bottle” to the top spot and confirmed Xtina as the second-biggest solo star of the nascent TRL teen-pop era. But Aguilera’s maturity would come rapidly: Stripped, her follow-up album, lacked the No. 1s of her debut but proved she was nobody’s No. 2, widely expanding her artistry in both depth and diversity. Decades and several more successful career transformations later, it still feels like the gold standard for this-is-me pop star statement albums; meanwhile, “What a Girl Wants” is still being sung by (male) pro athletes in unavoidable cell phone commercials.

Why Not Top 25? After 2006’s chart-topping Back to Basics, the hits dried up pretty fast: Aguilera never released another totally successful album, and her only major pop successes of the last 15 years have come as features.

DOJA CAT

Doja Cat
Photo : Jacob Webster

Her 21st Century in Pop: Doja Cat took a shortcut to mass visibility in 2018 with the hilarious viral one-off “MOOO!,” so by the time she’d parlayed that into actual pop stardom with her 2020 Hot 100-topper “Say So,” many expected her time in the limelight would be limited. In fact, it’s been anything but: Over the first half of the 2020s, you wouldn’t even need a full hand to count the number of pop stars more consistently productive, successful and attention-demanding than Doja Cat. It’s not always good attention she’s demanding – as her own fans will attest – but Doja has played the game brilliantly (if recklessly) for seven years now, and has a catalog of songs, albums, videos, performances and social media moments that stand with anyone else’s over that period. “MOOO!” still rules too, btw.

Why Not Top 25? The recency hurts, of course, as does the fact that as many brilliant moments as she’s strung together over the years, she doesn’t quite have the pull to stop the world with a release – evidenced by the fact that she’s yet to score a Billboard 200 No. 1 album.

DUA LIPA

Dua Lipa
Photo : Tyron Lebon

Her 21st Century in Pop: Dua Lipa wrote a set of “New Rules” for what a pop breakthrough looks like when she scored her first top 10 Hot 100 hit with the 2017 electro-pop post-breakup playbook following a series of hits in her native U.K., mixing her high-fashion sensibility and indie tastes to create an undeniably cool star. She’s doubled down on dance in the years since — including high-profile collabs with Calvin Harris (“One Kiss”) and Silk City (“Electricity”), plus her PNAU remix with Elton John (“Cold Heart”) – and fully established her nu-disco domination with her supernova sophomore album Future Nostalgia in 2020. Not even a global pandemic could keep people from dancing to the project’s string of smashes, most notably the unstoppable fifth single “Levitating,” which became the longest-charting song ever by a female artist on the Hot 100 (77 weeks) and finished as 2021’s year-end No. 1 Hot 100 hit. In 2023, the Albanian-British artist was the face of the blockbuster Barbie soundtrack, thanks to her mermaid cameo and party-scene-setting Hot 100 top 10 lead single “Dance the Night.”

Why Not Top 25? While Billboard selected Radical Optimism as one of the best albums of 2024 so far, thanks to its sure-footed lyrics and riskier productions, Lipa failed to crack the Hot 100’s top 10 with the project’s first three singles – but we’re still more than radically optimistic that she could rejoin pop’s upper echelon at any moment.

FUTURE

Future
Photo : Amanda Gorman

His 21st Century in Pop: Hard to remember a time when Nayvadius DeMun Wilburn, a.k.a. Future, debuted on the national stage and was considered something of a hip-hop gimmick, his singing and rapping blending together seamlessly in a post-Auto-Tune warble. Pluto had the early converts, and Honest had the pop-leaning defenders, but Future gradually established himself as a superstar for the streaming era, his melodic prowess, self-lacerating lyricism and croaked emotion spread across gritty mixtapes and guest-laden full-lengths. Depending on who you ask, Future’s professional apex could be the murky genius of his critically beloved 2015 project DS2, scoring back-to-back No. 1 albums in consecutive weeks with 2017’s Future and Hndrxx, earning the first Hot 100 No. 1 of his career with “Wait for U” in 2022, or helping lob the first grenade of the Drake-Kendrick Lamar feud with the smash hit “Like That” this year. Like the voice that made him famous, Future is a shape-shifting force of nature, and his various achievements have made him an indispensable part of modern hip-hop.

Why Not Top 25: Although he’s collaborated with everyone from Taylor Swift to Maroon 5 to Ariana Grande, following the 2014 crossover bid Honest, he’s mostly stayed pop-adjacent, while keeping both feet firmly in the hip-hop world — as Future rapped after that project, “Tried to make me a pop star, and they made a monster.”

JENNIFER LOPEZ

Jennifer Lopez
Photo : Ke.Mazur/WireImage

Her 21st Century in Pop: No one defined celebrity at the beginning of the 21st century quite like Jennifer Lopez. Music certainly wasn’t the only part of that – her film success and tabloid ubiquity were both crucial – but it still might’ve been the biggest; she released six top 10 Hot 100 hits over the first three years of the ‘00s, and helped define an era where hip-hop, R&B and pop all got more cuddly together than ever before. J. Lo bookended the next decade with a judging role on American Idol and a career-defining dramatic turn in the strip-club crime story Hustlers, then she kicked off the 2020s with a career victory lap co-headlining performance at the Super Bowl – all while never looking like she’s aged a single day.

Why Not Top 25? Great as her peak was – and she was our No. 1 Greatest Pop Star of 2001 – she ruled in a relatively weak era for pop stardom, and neither her signature hits or biggest albums still inspire quite the same reverence from pop fans today as the stars who ruled before or after her.

KELLY CLARKSON

Kelly Clarkson
Photo : Rob Verhorst/Redferns

Her 21st Century in Pop: The ultimate singing-competition success story has been proving for almost a quarter-century that the voting public got it 100% right back in 2002’s inaugural season of American Idol when they chose Clarkson as the show’s most promising pop star. Starting with her triumphant coronation ballad “A Moment Like This” topping the Hot 100, she’s been a fixture on the chart, scoring two more No. 1s — 2009’s “My Life Would Suck Without You” and 2011’s “Stronger (What Doesn’t Kill You)” – and 11 total top 10s, including the pop-rock all-timer “Since U Been Gone” (No. 2 peak in 2005). She’s continued to make her mark throughout the years, including with the evergreen modern Christmas classic “Underneath the Tree” in 2013 and the surprise No. 8-peaking megaballad “Piece by Piece” in 2016. In a full-circle career moment, Clarkson has returned to the medium that made her famous by coaching on The Voice for nine seasons and hosting five seasons (so far) of her namesake TV talk show, which has racked up 21 Daytime Emmys and launched her fan-favorite Kellyoke cover series.

Why Not Top 25: Clarkson has unquestionably endured as a multimedia celebrity, but her time as a hitmaking pop star was really limited to her first 10 years after Idol.

KENDRICK LAMAR

Kendrick Lamar
Photo : Courtesy of pgLang

His 21st Century in Pop: The most acclaimed rapper of the last 15 years arguably has the most bulletproof reputation in all of hip-hop – as J. Cole recently found out the hard (but not as hard as some) way, the only bad things you can really say about him as an artist are that he occasionally gets kinda preachy and he doesn’t come around often enough. And when Kendrick Lamar does come around, the results are spellbinding: Three award-winning, chart-topping, undisputed classic LPs (with underrated arguable fourths and fifths on both sides of that run), two decade-separated guest verses that both upended hip-hop’s entire hierarchy, and even a few Hot 100 No. 1s in there, just to show that he can.

Why Not Top 25? Even with those No. 1s, Kendrick Lamar just never really cared about making pop stardom the main thing, and (2024 aside) has largely shrunk from the spotlight when he didn’t absolutely have to be in it – during his most center-staged moment of the century, he was still sneering at Drake, “Only you like being famous.”

KESHA

Kesha
Photo : Christopher Polk/Getty Images for Clear Channel

Her 21st Century in Pop: The story of Kesha is still being reclaimed by the artist herself — during and following a years-long legal battle with producer Lukasz “Dr. Luke” Gottwald, the pop star has used her music to shake up her party-hard image, and communicate perseverance amid personal and professional complications. Yet anyone who experienced Kesha’s dollar-sign days, a blaze of Jack Daniel’s and glitter to kick off the 2010s, remembers one of the most dominant debut eras of the century. “TiK ToK” was the mega-selling first single, but “Blah Blah Blah,” “Your Love is My Drug,” “Take It Off,” “We R Who We R,” “Blow” and “Die Young” all reached the top 10 of the Hot 100 within a three-year span, as hedonistic turbo-pop took over the airwaves at the end of Obama’s first term. And Kesha was the master of ceremonies who was far more insightful than she let on — the emotional stunners on 2017’s Rainbow and 2023’s Gag Order resonated long after the party was over.

Why Not Top 25: As musically rewarding as Kesha’s recent output has been, she unfortunately couldn’t achieve the same hit rate as the first few years of her career — over the past decade, only one of her songs, 2017’s “Praying,” made it to the top 40 of the Hot 100.

LANA DEL REY

Lana Del Rey
Photo : Neil Krug

Her 21st Century in Pop: “This is the reason for half you bitches’ existence – including mine,” Billie Eilish informed the crowd during her guest appearance at Lana Del Rey’s 2024 Coachella headlining set. Well put: Del Rey was as influential as any artist of the past 15 years in changing the overall direction of pop music – providing a transformative downtempo alternative to the turbo-pop that ruled in the early ‘10s with something heavier, more theatrical and much more narratively murky, but all still just as alluring and world-building. You’d have an easier time building a list of major pop stars who haven’t rightly paid homage to the Venice Bitch in the years since.

Why Not Top 25? Formidable as the Cult of Lana has become over the past decade-plus, it is still mostly a cult – her actual top 40 presence has been more minimal than you’d think, with her only two Hot 100 top 10 appearances coming via an uncharacteristic EDM remix and a chill sesh alongside the world’s biggest artist.

LORDE

Lorde
Photo : Ilya S. Savenok/WireImage

Her 21st Century in Pop: One of the most instrumental figures in the trend of anti-pop stars becoming pop stars, Lorde stands as one of the most important singer-songwriters of the century so far. She exploded onto the scene with 2013’s “Royals,” a cool, biting takedown of pop maximalism and materialism that won a pair of Grammys topped the Hot 100 for nine weeks. Parent album Pure Heroine marked the first entry in a discography that has defined large swaths of young millennials and elder Gen Z, and was followed a year later by the hit Hunger Games: Mockingjay – Part 1 soundtrack, which displayed her keen curatorial ear (Grace Jones! Ariana Grande! Pusha T!) Her fearless approach to writing about the most uncomfortable intricacies of adolescence, self-worth and love came to a head with 2017’s Billboard 200-topping Melodrama, which earned an album of the year Grammy nod. Follow-up Solar Power gave her another Billboard 200 top 10 in 2021, but she wouldn’t have another culture-clutching moment until her appearance on Charli XCX’s “Girl, So Confusing” remix in 2024.

Why Not Top 25? She’s a songwriting savant with some indisputable pop classics, but her commercial success and the overall volume of her output is a bit lacking for her to crack the top 25.

MAROON 5

Maroon 5
Photo : David Tonge/Getty Images

Their 21st Century in Pop: Countless early-’00s pop-rock artists enjoyed brief moments in the sun before disappearing from top 40; a smaller group were able to sustain their runs for multiple hits and albums. Yet Maroon 5 exists in a class of its own, as a collective able to evolve with pop trends and keep rattling off sizable hits for nearly 20 years straight. Led by Adam Levine, who separated himself from the adult pop also-rans with his hunky charisma and lighter-than-air croon, Maroon 5 moved efficiently from coffee-shop pop-rock (“This Love,” “Sunday Morning”) to wedding-reception dance (“Moves Like Jagger,” “Sugar”) to top 40-baiting rap collaborations (“Girls Like You” with Cardi B, “Beautiful Mistakes” with Megan Thee Stallion), collecting family-friendly top 10 smashes all the while. There’s a good chance that your grandmother loves a Maroon 5 song, and that your adolescent nephew does too.

Why Not Top 25? Although Levine has established himself as a cultural figure thanks to a long-running gig on The Voice and some choice collaborations, Maroon 5’s musical influence has been relatively muted — not hit merchants, per se, but chameleonic enough to never establish one set formula that other pop-rock groups have copied.

MEGAN THEE STALLION

Megan Thee Stallion
Photo : Ramona Rosales

Her 21st Century in Pop: From her fiery flow – honed in the battlefield of cyphers in her Houston hometown – to her immaculate branding, Megan Thee Stallion is simultaneously one of the most unlikely and unpredictable pop stars of the 21st century. She truly broke into the mainstream with 2019’s saucy “Big Ole Freak,” an unabashedly Southern hip-hop joint that followed four mixtapes. By 2020, Megan became the hottest thing on the planet, landing a No. 1 single in “Savage” alongside Beyoncé, and taking home three Grammys (including best new artist) Despite a harrowing shooting and a nasty court battle that threatened to derail her career, Megan scored a conversation-dominating smash with “WAP” (with Cardi B) and this year launched a hugely successful North American arena tour. Between earning her B.S. in health administration while pursing her career and her evolution into a political pop powerhouse – even Vice President Kamala Harris has tapped her on the campaign trail! — Megan Thee Stallion somehow has it all, and continues to inspire the rest of us to get like her. 

Why Not Top 25? With her true breakthrough happening just five years before the cutoff and the lack of a No. 1 album, Megan isn’t quite one of the top 25 pop stars of the century (yet).

MISSY ELLIOTT

Missy Elliott
Photo : Gap via Getty Images

Her 21st Century in Pop: Missy was easily the baddest chick on the block in the early 2000s, with a series of game-changing albums and singles that treated both pop and hip-hop as Play-Doh, to be stretched every which way and ultimately re-molded in whatever image she saw fit. She approached music videos the same way: Her (at times literally) shape-shifting approach to the medium set new standards for outside-the-box imagination in hip-hop, while also still being accessible and popular enough to clean up at the VMAs. Missy spent the first five years of the millennium being absolutely light years ahead of the game; when she took a step back after 2005’s The Cookbook, it felt like she was just giving everyone else a chance to catch up.

Why Not Top 25? Unfortunately, Missy never fully stepped back into the spotlight after 2005 – despite popping up every so often over the past two decades with new (and frequently excellent) singles, guest verses or live appearances, she hasn’t released an album since then, and only set off on her first-ever national headlining tour this July.

NELLY

Nelly
Photo : Tim Roney/Getty Images

His 21st Century in Pop: A few weeks into the new millennium, three beats rang out, a voice called out “HOT S–T!,” and Cornell Haynes Jr., the St. Louis rapper known as Nelly, burst into the spotlight by rejiggering the melody of “Down Down Baby.” “Country Grammar (Hot S–t)” was an electric debut from the Midwest MC, establishing a playful flow and mainstream-ready charm that helped turn his 2000 debut Country Grammar into a mega-seller. His follow-up, 2002’s Nellyville, was even bigger, thanks in part to the club-dominating “Hot In Herre” and R&B juggernaut “Dilemma” with Kelly Rowland; those two singles spent an astonishing 17 weeks combined atop the Hot 100 in 2002, ahead of Nellyville scoring an album of the year Grammy nod. Nelly spent the next decade rattling off a variety of top 10 hits, from the crunk-adjacent “Grillz” with Paul Wall and Ali & Gipp to the “Cruise” remix with Florida Georgia Line.

Why Not Top 25: Nelly was ubiquitous during the first 10 years of the 21st century, but the past 15 have been light on crossover hits and with bigger gaps in output — understandable for a veteran artist, but enough to blunt his modern appeal.

OLIVIA RODRIGO

Olivia Rodrigo
Photo : Nick Walker

Her 21st Century in Pop: For any pop artist, watching your debut single start atop the Hot 100, spend eight weeks there and become a year-defining sing-along would equal success beyond your wildest dreams; for Olivia Rodrigo, her 2021 breakthrough simply functioned as the first box marked in a sprawling checklist. Since then, the former High School Musical: The Musical: The Series star has collected two No. 1 albums (2021 debut Sour and 2023 follow-up Guts), two more Hot 100 chart-toppers (spunky Sour pop-punk anthem “Good 4 U” and sweeping Guts kiss-off “Vampire”), a best new artist Grammy and millions of screams as an arena headliner. And despite the Disney background and crossover success, Rodrigo’s guitar-heavy aesthetic — as well as her love for ’90s alt vets, covering Veruca Salt live and enlisting The Breeders as an opening act — prime her as a new-school rock star as much as a pop phenom.

Why Not Top 25: Rodrigo wasn’t alive at the beginning of the century, and has only been a star for the past three-and-a-half years; she’s accomplished a ton in a relatively short amount of time, but it’s still early days. (Don’t be shocked to see her on this list if we update it in 25 years, though.)

P!NK

P!ink
Photo : Christian Jakubaszek/Getty Images

Her 21st Century in Pop: P!nk never fit into the pop star mold, with her purposely rebellious image acting as the rough-edged answer to the bubblegum boom of the turn of the century. But her hits were undeniable: After her feisty R&B-inspired breakthrough with 2000’s “There You Go,” her top 40 cred was cemented as part of the quartet behind the Moulin Rouge-commissioned 2001 Hot 100 No. 1 cover of “Lady Marmalade.” That was just one of her four No. 1s (from 15 top 10s), as she also topped the chart with 2008’s sassy “So What,” 2010’s outcast anthem “Raise Your Glass” and 2013’s Nate Ruess duet “Just Give Me a Reason.” The scrappy artist has taken her career to new heights thanks to her acrobatic live performances — most notably her gorgeous “Glitter in the Air” routine at the 2010 Grammys — and is still smashing Billboard Boxscore records with Cirque du Soleil-worthy aerial feats at every show.

Why Not Top 25? She’s a touring legend with a deep catalog, but she’s never strung enough huge hit songs and albums together in any one era to truly dominate the pop landscape.

POST MALONE

Post Malone
Photo : Adam DeGross

His 21st Century in Pop: Post Malone seemed like a smart bet for one-hit wonder status after his somewhat uhhh sure breakthrough “White Iverson” reached the Hot 100’s top 15. Then he was a two-hit wonder, then a three-hit wonder, and pretty quickly he was just one of the biggest hitmakers on the planet, now with six Hot 100 No. 1s to his name. While he started in rap, he’s flirted plenty with R&B, metal, alternative and now country – and though you’d be unlikely to ever confuse him with Justin Timberlake, he’s ultimately revealed himself to basically be a pop star at his core, with hooks, pipes, charisma and dance moves for days. Even “White Iverson” is basically bubblegum in retrospect.

Why Not Top 25? Though he feels like he’s already been with us forever at this point, Post Malone has really only been a star for eight years now – and about half of those years were looking kind of dicey, as Posty tried to figure out his place in a post-pandemic world, until he got some help in 2024 from Beyoncé, Taylor Swift and (of course) Morgan Wallen.

SEAN PAUL

Sean Paul
Photo : Scott Gries/Getty Images

His Decade in Pop: There is no artist as synonymous with dancehall’s Stateside crossover peak than Sean Paul: From 2002’s Hot 100-topping “Get Busy” to his 2016 Sia-assisted chart-topper “Cheap Trills,” Paul has been the defining face and voice for the genre in the U.S. His booming, room-rattling voice and rapid-fire delivery helped make dancehall unavoidable on top 40 radio, both on his own (“Gimme the Light,” “Temperature”) and through seismic collaborations with Beyoncé (“Baby Boy”), Rihanna (“Break It Off”) and Clean Bandit (“Rockabye”). For most of the decade’s first half, there was not a dancefloor that could resist the allure of Paul’s voice: Dripping with equal parts sensuality and swagger, he injected Island flavor into the American mainstream in a way that sidestepped gimmickry. In recent years, he’s focused on the Latin music market, collaborating on chart-topping records with Enrique Iglesias (helping his pivotal “Bailando” cross over in the early 2010s) and Feid (2023’s “Nina Bonita”).

Why Not Top 25? After a strong hitmaking run as a leading man in the 2000s, his only major hits in the 2010s came as a guest star — and 13 years without a Hot 100 entry as a lead artist is hard to ignore.

SZA

SZA
Photo : Anna Webber/Getty Images for Spotify

Her 21st Century in Pop: With release of her 2017 debut LP Ctrl, SZA, the St. Louis-born, Jersey-bred singer-songwriter effortlessly positioned herself as the heir to Lauryn Hill’s elusive throne. Her confessional, messy, audacious songwriting spoke to the hearts of millions around the world – particularly Black women working through their 20s. Ctrl came up short at the Grammys and failed to send a single to the Hot 100’s top 20, but eventually won the long game, shifting over three million units and setting the groundwork for 2022’s SOS. SZA’s sophomore album spent a whopping 10 weeks atop the Billboard 200, spawning five Hot 100 top 10 hits (including her first No. 1 “Kill Bill”) and providing a credible challenger to Taylor Swift’s mega-blockbuster Midnights for album of the year at the 2024 Grammys. Outside of her half-decade-separated studio albums, SZA earned an Oscar nod for Black Panther Kendrick Lamar duet “All the Stars,” scored top 10 hits alongside Maroon 5 and Drake, and helped keep a bright light on R&B as other genres threatened to leave it in the streaming dust.