A Timeline of Bad Bunny’s Biggest Career Moments, From Charts To Protests & More

The Early Singles (2016 and 2017)

Bad Bunny’s breakthrough—from Soundcloud to airplay and major streaming numbers—came in 2016 via “Diles,” a super-sexual slow-burner alongside Ozuna, Farruko, Arcangel and Nengo Flow. His growing following in Puerto Rico’s underground now began to reach the Latinx diaspora, and several more singles came close in order, maintaining the momentum. Among them is “Soy Peor,” where Benito takes center stage, and “Chambea” and “Krippy Kush,” both pumped-up, party-ready cuts that felt like a rush by comparison. Already embraced by DJs at Puerto Rico’s nightclubs, he soon makes a big impression on Daddy Yankee’s “Vuelve” too, in case anyone was doubting his cred.

It’s during this time that Bad Bunny’s signature vocals—strikingly low, like a perpetual boom that never explodes—make clear to reggaeton and Latin trap fans that nobody else flows like he does. In fact, Benito is beginning to stand out as a pioneering artist.

Cardi B’s Seal of Approval

In a year of massive collabs—”MIA” with Drake and “Te Guste” with J.Lo, to name a couple—“I Like It” is easily Bad Bunny’s most culturally impactful work. Cardi B runs this show, absolutely, but Benito and buddy J Balvin add a litany of lyrical references to Latin music old and new, from Celia Cruz to Benito mentioning “Chambea” and, for the first time on a major level, signaling to the new wave of urban: “This is the new religion, bang, en latino gang, gang,” he raps.

The trio’s performance of the song at the American Music Awards in October is another major milestone for Bad Bunny, and not only because he performed with Queen Cardi before millions of U.S. viewers. It’s the debut of his third eye, painted on his forehead, that gets a lot of folks’ attention: nobody, much less a Latinx male artist, hs showed up to an awards show sporting one. Now, his obvious pro-individuality stance on style—his baby blue patterned suit on the red carpet is unexpected, too—adds another layer to what makes Bad Bunny so singular.

We’d be remiss not to mention the remix of Nío Garcia, Darrel and Casper Mágico’s “Te Boté” here, of course. (Nicky Jam and Ozuna are in there too, but Bad Bunny’s line, “Baby, la vida e’ n ciclo/ Y lo que no sirvo yo no lo reciclo” is undeniably most memorable.”) The hit went so long, and so wide, spending nearly two-and-a-half years on the Billboard charts, that it deserves heralding as a massive milestone in Latinx music—and Bad Bunny certainly contributed to that success.

“Estamos Bien,” He Says

The single was released the summer after Hurricane Maria, while the entire archipelago still grappled with the historic storm’s devastating effects, so for many Puerto Ricans it was a rallying call for continued resilience.

The whole world was following the story of the tragically slow post-storm recovery of Puerto Rico and nearby islands, and everyone was also looking at Bad Bunny, as he was fresh off the AMA’s performance. This is when we understood Bad Bunny to be not only an artist, but also an advocate for his people: He used his late-night TV debut on the Tonight Show in September of 2018 to speak out against Trump’s “denial” of how many people died as a result of Maria, and pointing out how, a year later, so many Puerto Ricans were still without electricity.

'X100PRE,' a Holiday Surprise

Bad Bunny’s debut album, released with little notice on Christmas eve, brought more joy than Santa ever could—for his fans, anyway. And the surprise wasn’t the best part, either. It’s the actual album, a total masterpiece that spans genres and pushes barriers and totally confuses people who think Latinx urbano is one thing or another. Bad Bunny taught us on X100PRE that there are no boundaries before him: His sound is whatever he wants it to be, whether that means a sappy emo-leaning number (“Si Estuviésemos Juntos”) or a pop-punk tinged bop (“Tenemos Que Hablar”) or a trap track underscored by lyrics that champion individuality (“Caro”).

The videos rolled out alongside these songs, by the way, are milestones in themselves—especially “Caro,” for its spirited gender play and pro-LGTBQIA+ messaging, and “Solo de Mi,” employed to call for an end to gender-based violence, an especially acute issue in Puerto Rico.

San Juan Homecoming

Bad Bunny’s three-night stand at San Juan, Puerto Rico’s famed El Choliseo belongs on this timeline of events because he made it so: It was an experience as much as it was an event. Forty-plus songs were performed each night, guests were major, and there were attractions set up throughout the venue (video games, a nail salon, horoscope booths). At this point, Bad Bunny’s fame is soaring globally, yet he pays special attention to everyone back home who loves him: that time and care was truly special.

Man of the People of Puerto Rico

Along with Residente, Bad Bunny showed up at then-Puerto Rico Governor Ricardo Rosselló’s mansion in the middle of the night early on in the year. A chunk of the politically charged adventure, centered on the island’s high rates of femicides, was streamed live on IG.

But later that summer, as protests against Rosselló swelled in Puerto Rico, Bad Bunny, despite how high-profile he’d grown to be, joined the people in denouncing the now-former governor for the offensive and homophobic commentary of a leaked chat. He was loud on socials, but most importantly, he literally, actually, physically showed up—at one of the biggest demonstrations during the movement, no less, alongside Ricky Martin, Residente, and iLe.

Pressure from the people led Rosselló to resign, but Bad Bunny helped amplify the people’s voices, no doubt.

An Oasis of Solid Jams

We include this collaborative EP with Balvin because their friendship was at peak cuteness at the time, and also because it had the “biggest streaming debut” of a Latinx album in 2019. And while it didn’t chart new sonic territory for either of them, the fact remains that it’s dense with hits, like the lloripari anthem “La Canción” and “Yo Le Llego.”

Benito Reminds Us 'YHLQMDLG'

This video album has everything: perreo and drag combined, a reggaeton tribute medley with Jowell and Randy and Nengo Flow, a tribute to Puerto Rico, another perfectly sing-along-able emo song, and more. Seriously, though, if the world wasn’t sure already that Bad Bunny does whatever he wants always, on Feb. 29 this year, he made sure everyone understood.

September’s Quarantine Concert Parade

As much as we loved his quarantine livestream, watching Bad Bunny roll through New York City neighborhoods, performing career-spanning hits for almost two hours was simply unprecedented. He’s not the first artist to perform in such a manner, but there’s no denying he’s the first-and only-one to do it amid a global pandemic. Including virtual duets with Sech, Mora and Balvin, Bad Bunny’s performance attracted more than 1.4 million viewers to his YouTube channel.