After his first reggaetón track went viral on SoundCloud in 2016, Bad Bunny left his job as a supermarket bagger and stepped into public view. With eccentric haircuts, painted nails, skirts, and fluorescent glasses, he disrupted the hyper-masculinity that defined the genre for decades: a body that didn’t ask for permission, and the attitude that later transformed him into a political icon. By 2018, the artist (real name Benito Antonio Martínez Ocasio) was already Puerto Rico’s biggest musical export; by 2019, the most influential singer in the Spanish-speaking market; and since 2020, the most listened-to artist in the world. 

However, even in Latin America, his own cultural territory, he has long been viewed with suspicion. Eurocentric criticism, also dominant in the Global South, never forgave reggaetón for having transformed the body, desire and excess into political language. Middle-class, predominantly white listeners dismissed it as vulgar “pornographic music”, while early 00s critiques in Puerto Rican media went further, criminalising the genre for its aesthetics. Its detractors demanded a translated, sanitised version, reshaped to fit the dominant English-speaking values.

To understand Bad Bunny’s refusal to be softened or translated, you need to understand Puerto Rico: a territory shaped by its colonial condition, disguised as a “Commonwealth” by the US and exploited as a strategic and military enclave rather than a social equal. Lacking sovereignty and living under constant cultural scrutiny, the island developed an urgency of identity that runs through its music, where each genre becomes an act of resistance, a war of colour and sound fought through bodies, streets, and dance to keep Puerto Rican identity alive.

The recent celebration of Bad Bunny in the United States, including a Best Album of the Year win at the 2026 Grammys and his forthcoming headlining show at the Super Bowl, functions as the cultural turning point of a centenary identity struggle: the moment when Puerto Rico, and Latin America at large, ceases to justify itself or depend upon translation to be understood. The US is now the one forced to accept a Latin centrality that can no longer be ignored, domesticated or treated as secondary.

It’s a clear fracture. While Hispanic artists continue to dominate both US and global charts, Benito’s Super Bowl performance also arrives in the middle of brutal ICE raids across the States, which disproportionately target Latino and Hispanic communities. It is in this context that Bad Bunny emerges as a figure who signals that this transition is forcing the United States to recognise itself as part of a broader, more diverse, and Spanish-speaking América (yes, with an accent).

Below, we break down nine key chapters from Bad Bunny’s career that led him to become the profoundly anti-colonial voice that he is today. 

2017 – “CARO” AND TOXIC MASCULINITY

In a scene dominated by hypermasculine codes of trap and reggaetón, Bad Bunny started making appearances wearing painted nails and dresses, without framing it as provocation or statement. The gesture mattered because it refused justification. 

This refusal was not improvised. From an early age, Benito had already learned to move outside the limits imposed on masculinity. He has recalled how some of his favourite moments with his mother were spent wandering through women’s clothing sections in shopping malls, drawn to the colours, cuts, and combinations unavailable to him in men’s fashion. “When it was my turn to buy clothes, it was always the same jeans and shirts in different sizes. Women’s clothing had freedom; men’s didn’t. There’s definitely a double standard,” he said in a 2021 interview with Allure.

SEPTEMBER 2018 — “ESTAMOS BIEN” AND HURRICANE MARÍA 

“A year after the hurricane, there are still people without electricity in their homes. More than 3,000 people died, and Trump is still in denial. But you know what? We’re good, with or without $100 bills [...] And we’re going to be even better, Puerto Rico.”

Bad Bunny said these words during his first-ever appearance on US television performing “Estamos Bien” (“We’re Good”). Standing on the stage of The Tonight Show Starring Jimmy Fallon, he chose not to introduce himself with spectacle or gratitude, but with grief and accusation. He was preparing to release his debut studio album, X 100PRE, after nearly nine months of self-imposed silence, caused not only by the shock of sudden global fame, but by a historical rupture that reshaped Puerto Rico entirely: Hurricane María.

The aftermath was devastating. More than 200,000 people were displaced. Entire regions of the island were left without electricity for months, some for over a year. The death toll, initially minimised by the US. government, would later be confirmed to be in the thousands. 

DECEMBER 2018 – “SOLO DE MÍ” AND GENDER-BASED VIOLENCE 

“Solo de Mí” is a song that directly confronts one of the most pressing issues in Latin American society: violence against women. In the video, a woman faces the camera in a fixed shot while visual effects simulate the appearance of bruises and wounds as she sings. By the end, she wipes away the marks and goes out to a club to dance with friends, a gesture of resistance. The lyrics deliver a clear message: “I’m not yours, nor anyone else’s. I belong only to myself.”

Bad Bunny introduced the song on Instagram, emphasising that it was meant as a protest against gender-based violence and the intolerable number of women killed every month: “Less violence, more perreo [reggaeton traditional dance, similar to twerking] (and if she wants to, let her dance alone and don’t bother her)”. Later, in Rolling Stone, he added: “As a human being, violence against women affects me. I will do everything I can to fight it. My message should not be seen as feminist, but as universal”.

2019 - “AFILANDO LOS CUCHILLOS” AND CRITICISING CORRUPTION 

On January 10, 2019, alongside fellow Puerto Rican rapper Residente, Bad Bunny stood outside La Fortaleza, the governor’s residence, demanding accountability for a wave of violence ravaging the island. Puerto Rico had already recorded dozens of murders in the first days of the year, including the fatal shooting of openly gay trap artist Kevin Fret, and both artists used social media to document their attempt to be heard. 

 Denied entry, they spoke to guards, critiqued plans to close hundreds of schools, and condemned a “prehistoric” educational system incompatible with younger generations. Eventually, public pressure, amplified by millions online, finally forced Roselló to meet with them. The meeting produced no real change and requests for follow-ups were ignored.

Later that year, in the wake of leaked Telegram messages exposing racism, sexism and homophobia within Roselló’s government, Bad Bunny joined protestors on the streets. Amid the uprising, Bad Bunny and Residente recorded and released music that openly criticised Roselló’s corruption and complicity in the scandal.

When Roselló finally announced his resignation on July 24, the streets erupted, not with solemn anthems but with reggaetón. The main theme was “Te Boté”, a hit popularised by Bad Bunny’s line, which literally means “I kicked you out of my life”: Puerto Ricans celebrated their own refusal to endure corruption while recognising Benito’s role not as a detached pop star, but as a visible participant in their struggle.

2020 - “YO PERREO SOLA” AND TRANS RIGHTS

During his second appearance on The Tonight Show with Jimmy Fallon, Bad Bunny wore a skirt, diamond earrings, a pink blazer, and a T-shirt reading: “They killed Alexa, not a man in a skirt.” The message referred to the murder of Alexa Neulisa Luciano Ruiz, a trans woman killed in Puerto Rico just days earlier after being targeted for using the women’s restroom at a McDonald’s in Toa Baja.

At the time, media outlets and police reports repeatedly misgendered Alexa, reducing her identity to sensationalist and transphobic language: “a man in a skirt”. Bad Bunny’s intervention cut through that erasure with a sentence worn on the body, broadcast live on American television.

A month later, that stance shifted from mourning to assertion with “Yo Perreo Sola”, where Bad Bunny appears in drag, singing from the perspective of a woman who wants to dance alone, unbothered, unclaimed. The video ends with a clear directive: “If she doesn’t want to dance with you, respect it.”

2022 - “EL APAGÓN” AND THE BLACKOUT

In 2022, Bad Bunny’s fourth album Un Verano Sin Ti became the most-streamed album of the year on Spotify (and, later, of all time). Rather than diluting his political stance, this level of commercial success made it impossible to ignore. One standout song from the project, “El Apagón”, radiates particular pride in belonging to the island. Its final section, driven by hard techno, shifts perspective to a woman singing openly against the gentrification of the island: “I don’t want to leave here, they should be the ones to go / This is my beach, this is my sun, this is my land, this is who I am.”

Six months after the album’s release, Benito chose to expand the song’s message through its visuals. What emerged was a documentary exceeding 20 minutes. Through testimonies from residents, activists, and journalists, “El Apagón” links everyday precarity, the collapse of basic services, and the inability to remain in one’s own neighbourhood to a colonial economic model that treats the island as a commodity. Privatised beaches, tax laws designed to benefit US investors, and communities pushed out in the name of development. 

2024 - “MOSCOW MULE” AND PUERTO RICAN INDEPENDENCE 

Despite repeatedly speaking out against internal and external forces that have harmed Puerto Rico, Bad Bunny had largely avoided direct intervention in the island’s electoral politics. “Puerto Rico has given an organic endorsement,” Bad Bunny told thousands at a public rally in 2024. “It’s you, the people of Puerto Rico, who have made it clear that on November 5th, we must vote for Juan Dalmau and the Alianza.”

Dalmau ran as the candidate of a new third-party coalition that united the Puerto Rican Independence Party with the Citizens’ Victory Movement, a political force founded in 2019 that sought to break with decades of partisan stagnation. Together, they advocated for the full independence of Puerto Rico from the US, and, with Bad Bunny’s endorsement, the independence movement became the country’s second-largest political force for the first time in history. 

2025 - “NO ME QUIERO IR DE AQUI” AND THE US MARKET 

The release of his album Debí Tirar Más Fotos became an instant landmark in Latin American music. Yet the celebration unfolded against a shifting political backdrop: the re-election of Donald Trump and the renewed force of an openly anti-Hispanic agenda in the United States.

When Bad Bunny announced his world tour, one detail immediately stood out. The schedule included 46 stadium dates across the globe and an additional 31 shows in Puerto Rico, but none in the continental United States. “There were many reasons why I didn’t show up in the US, and none of them were out of hate,” he explained. “The problem was that ICE could literally be outside the concerts. That was something we talked about and were deeply concerned about.” He later added a line that landed as a quiet dismissal of a market long considered the most important in the world: performing in the United States, he suggested, “had become unnecessary”. 

The decision aligned seamlessly with the album’s broader argument, Spanish-speakers no longer asking for permission, and Puerto Rico no longer positioning itself around US validation. More than 600,000 people attended Bad Bunny’s residency, generating an estimated $700 million for the island’s economy.

2026 - THE GRAMMYS AND ICE

2026 was the first time Bad Bunny won a Grammy in the ‘big three’ categories at the ceremony, crystallising his position at the top of the musical mainstream. True to the spirit of DtMF, Bad Bunny remained accountable in his acceptance speech for album of the year:  “ICE out. We are not savages, we are not animals, we are not aliens; we are human,” he declared defiantly before calling on Latin Americans: “If we are going to fight, we have to do it with love. Let's not hate them, but let's love our people, our family, our culture.”

It’s in view of all of this that Bad Bunny’s upcoming Super Bowl performance emerges as particularly significant. It speaks to a future in which Latin music, and Spanish, cease to ask for permission. The world will dance this weekend, but it will also have to learn how to listen without translation.

Bad Bunny performs at the Super Bowl LX Halftime show this Sunday (February 8).