Billboard’s Greatest Pop Stars of the 21st Century: No. 23 — Bad Bunny

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 and No. 24 stars, and now we remember the century in Bad Bunny — who grew from Latin trap phenom to globe-conquering superpower and transformed what it means to be a pop star in the U.S. and beyond.

It’s easy to forget in 2024 how unusual the concept of a foreign-language U.S. pop star was as recently as last decade. Even as Latin pop enjoyed a massive crossover moment at the turn of the century, and reggaetón became a global force in the mid-’00s, the only artists able to regularly dominate the U.S. mainstream were those who performed in English (or collaborated with English-language hitmakers). Daddy Yankee was as legendary a 21st century reggaetón artist as they come – his 2022 sendoff album was called Legendaddy – but his signature hit, the all-Spanish  “Gasolina,” still topped out at No. 32 on the Billboard Hot 100 in 2005. Even his historic, chart-conquering Luis Fonsi teamup “Despacito” needed a Justin Bieber remix to get over the Hot 100’s top in 2017, and neither Fonsi nor Yankee has made the chart’s top 20 again since. 

And then came Bad Bunny. The Puerto Rican artist born Benito Antonio Martinez Ocasio didn’t transform global pop music overnight, but over the course of his six-year rise to dominance, he infiltrated the mainstream in a way no other Spanish-language artist – no foreign-language artist of any kind, really – ever quite has. That’s because not only did Bad Bunny establish himself as one of the most reliable hitmakers on the planet (and in the U.S. specifically) while also becoming one of the most recognizable faces and personalities in pop culture at large, but he did it all while seemingly making no artistic concessions to anyone – not to radio, not to trends, and certainly not to the English-speaking world.

Bad Bunny first made his presence known in 2016, after his single “Diles” – released on SoundCloud, while Ocasio was still working as a supermarket bagger – attracted enough viral attention to both get him a label deal with Hear This Music and Rimas Entertainment and earn a remix featuring established reggaetón hitmakers Farruko, Arcángel and Ñengo Flow (and a fellow rising star in Ozuna). The song didn’t make much chart impact, but became a slow-burning streaming success – and later that year, Bad Bunny released “Soy Peor,” which would become his first entirely solo hit when it peaked at No. 19 on the Hot Latin Songs chart in September 2017, establishing him as a leading voice in the burgeoning Latin trap scene. 

Over the next year, Bad Bunny would also become a fixture on the Hot 100, appearing on hits alongside Becky G (“Mayores”) and Enrique Iglesias (“El Bano”), while also contributing his growing star power to All-Star cuts like “Krippy Kush” and “Te Boté,” the latter his first top 40 entry on the chart. While Bad Bunny was just one artist of many on the latter two songs – with a combined 10 total credited names between them – he stood out for both his distinctive voice, a congested-but-buttery croon which also made his trademark artist tag (“Bad Bunny bay-beh!!”) instantly unforgettable, and for his impeccable fashion style, an unconventional mix of the flamboyant and the basic that always seemed to land within the realm of timeless cool.

It all led up to his 2018 feature appearance on American rap superstar Cardi B’s “I Like It,” one of pop’s great star-making moments of the 21st century. While Bad Bunny did not yet have the household name recognition of either Cardi or fellow guest reggaetonero J Balvin – who’d recently scored a massive U.S. crossover moment of his own with the Willy William collab “Mi Gente,” even landing Beyoncé for the song’s remix – his verse still kinda stole the show, from its opening “chambea, chambea” chant. Wearing cat-eye sunglasses and a Puerto Rico World Baseball Classic jersey in the song’s hugely popular music video, Ocasio already looked like an icon in the making. The song reached No. 1 on the Billboard Hot 100, and ensured that all eyes everywhere were now on Bad Bunny. 

The heat from “I Like It” did not take long to translate to Bad Bunny’s career as a leading man. Just a few months later, he returned with “MIA,” which landed a guest verse from perhaps the only hitmaker with even more juice than Cardi B in 2018: Drake, in the midst of a year where he’d spend a combined 29 weeks atop the Hot 100 with Scorpion singles “God’s Plan,” “Nice for What” and “In My Feelings.” Not only did the Canadian-born superstar play the hook man for Bad Bunny’s new single, he actually sang in Spanish for it – showing that this early in his rise, Benito already had the clout to get the English-speaking pop world to come to his turf. “MIA” was another enormous success for Bad Bunny, reaching No. 5 on the Hot 100 and enduring for long enough to end up the No. 1 year-end single on the 2019 Year-End Hot Latin Songs chart.

Amazingly, Bad Bunny’s entire rise to stardom transpired before he even released his debut album. That came at the tail end of 2018, however, with X 100pre. Rather than cash in on his two years of hits and big-name collabs to that point, Bad Bunny’s debut album featured only a couple of his previously released singles and just a few guests, with “MIA” stuck at the end like a bonus track. The album drew rave reviews and reached No. 11 on the Billboard 200, hanging around the chart well into the next decade and ultimately spending 177 weeks on the listing, confirming that Bad Bunny was already much more than just a singles artist. 

In June 2019, while Bad Bunny was still spinning off X 100pre hits, having further success with singles alongside hitmakers Tainy (“Callaíta”), Lunay (“Soltera”) and Jhayco (“No Me Conoces”) and taking a break in between legs of his first arena tour, Bad Bunny would further electrify his now-global audience by reteaming with his “I Like It” collaborator J Balvin for the Oasis EP. Despite having just eight tracks, the set made both the top 10 on the Billboard 200 and the top 10 of Billboard’s year-end staff albums list for 2019. Perhaps most importantly, while Bad Bunny was unquestionably the little brother of the two from a star perspective on “I Like It” just a year earlier, by the time of Oasis he and Balvin were clearly on even footing as the two leading hitmakers in reggaetón and Latin trap. 

But while Balvin’s stateside star would fade somewhat as the decade turned to the 2020s, Bad Bunny’s would only get brighter. In 2020 alone he would release a trio of albums – YHLQMDLG (short for Yo Hago Lo Que Me Da La Gana, “I Do Whatever I Want” in English) in February, castoffs compilation Las Que No Iban a Salir (The Ones That Were Not Coming Out) in May and El Último Tour del Mundo (The Last Tour in the World) in November – that continued to expand his sound and his global profile, attracting rave reviews (even from many listeners and publications who had not traditionally shown interest in Latin pop or reggaetón). His albums became event releases – doubly so because he started scheduling them around major calendar events (X 100pre on Christmas Eve, YHLQMDLG on Leap Day, El Último on Thanksgiving, etc.) What’s more, in December, Último made history by debuting at No. 1 on the Billboard 200, marking not only Bad Bunny’s first appearance atop the chart, but the first entirely Spanish-language No. 1 album in the chart’s near-60-year existence.

In 2021, Bad Bunny made the jump from pop hitmaker to unavoidable celebrity. He scored a brief cameo in F9, the latest installment of the blockbuster Fast & Furious franchise, and started appearing in commercials for Cheetos and Corona, the latter featuring his bilingual bantering with American rap icon Snoop Dogg. More unexpectedly, he launched a wrestling career – at first just performing his wrestling-themed “Booker T” at the Royal Rumble, then getting in the ring himself, both on his own and as part of a tag team with fellow Puerto Rican Damien Priest. He also used his newfound industry influence to help facilitate comeback moments for some of his hitmaking favorites of yore – enlisting Aventura for his hit “Volvi” and both co-writing and co-producing El Playlist de Anoche with Tommy Torres, giving each their biggest spotlight moment in years, if not decades. 

But as much as Bad Bunny accomplished in the first five years of his career, it turned out to all be the prelude to 2022. That May, he dropped Un Verano Sin Ti (A Summer Without You) – 23 tracks, again entirely in Spanish, with no major English-language guests, and with only closer “Callaíta” having been previously released. Like Último, it debuted atop the Billboard 200 – but unlike Último, it stayed there, spending 13 weeks at No. 1 on the listing, with at least 8-10 of its tracks also populating the Hot 100 during any given week that summer. Though no one single from it was really big enough to bring Verano to larger consciousness on its own, the album was so varied in sound –  with tracks ranging from the sublime “Neverita” to the booming “Titi Me Pregunto” to the party-starting “Después de la Playa” – but so coherent in overall feeling, that different songs from it popped off at different times (and with different audiences). It ended 2022 as the No. 1 album on both the Year-End Billboard 200 and the Billboard staff’s Albums of the Year list, and also earned Bad Bunny his first Grammy nomination for album of the year.

Between 2022 and 2023, his stateside visibility took yet another step up, as he co-starred (and had a big fight scene) with Brad Pitt in the action flick Bullet Train, pulled double duty hosting and performing on Saturday Night Live, and dominated the 2022 VMAs remotely from his headlining gig at Yankee Stadium – part of his globetrotting World’s Hottest Tour – where he won the artist of the year moonperson. (He also made headlines for kissing a male backup dancer during that performance, further demonstrating an allyship that has made him an icon for the LGBTQ community, a rarity for trap or reggaetón artists.) He also began dating American superinfluencer Kendall Jenner, news of which was met with some trepidation from his core fanbase, but which cemented him as a tabloid fixture, and half of one of pop culture’s preeminent 2020s power couples. Before 2023’s end, he even released another album: Nadie Saber Lo Que Va a Pasar Mañana, which also debuted atop the Billboard 200, albeit without quite the rapturous acclaim or staying power of Verano. 

In 2024, Bad Bunny stands as simply one of the biggest culture-movers in music. The list of accolades and accomplishments he’s racked up in his career to this point is staggering, but his truest legacy may simply be proving that you can be the greatest pop star in the world – and he was ours for 2022 – without compromising your music, your image or your language for the American market. When Bad Bunny gets up at an award show this decade and accepts entirely in Spanish, he does it without apology or hesitation, and nobody even blinks at it. Now, it’s easy to see an artist like Karol G or Peso Pluma following their way through some of the doors he’s opened. And that’s the power of Bad Bunny: to be such an obvious, all-encompassing superstar that you forget just how long – and until how recently – those doors had been closed in the first place. 

Read more about the Greatest Pop Stars of the 21st Century here and check back on Thursday when our No. 22 artist is revealed!

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