An air of discomfort swept over Boston’s Agganis Arena earlier this year as 24-year-old Puerto Rican trap idol Bad Bunny extended the length of his embrace with a young boy he invited to perform on stage.

It was the kind of brotherly hug one might see an older sibling give his younger brother before leaving to college. Just as the hug seemingly ran its course, Bad Bunny reaffirmed his tight grip. The rapper repeatedly whispered in the boy’s ear. Tears of joy and encouragement streamed down both their faces. Bad Bunny was clearly uplifting the teen boy, and encouraging him to follow his dreams. But the length of the embrace had many in the room – particularly Latinx men – uncomfortably fidgeting while waiting for it to end. This moment perfectly encapsulated Bad Bunny’s implausible grip on Latinx culture.

Shattering notions of Latinx masculinity — from painting his nails, to encouraging women to refrain from over-grooming for men’s benefit, to even suggesting women deserve polyamorous relationships — Bad Bunny has steadily led the often-hyper-masculine Latin trap surge since seemingly appearing out of thin air some two years ago. And he’s making his name known with English-speaking audiences, preparing them for his take over, despite having yet to release an album or even so much as a mixtape.

In the age of a never-ending bolt by trap artists to release as much music as possible to game streaming numbers, Bad Bunny’s lack of a cohesive release can feel like a string of missed opportunities. With every passing milestone el Conejo Malo reaches, the moment seems ripe for him to swoop in with his promised full-length, La Nueva Religion, or even the much-hyped, in-the-works collaborative album with J Balvin, Oasis. But Bad Bunny patiently bides his time, never straying far from the spotlight. Whether it be via one of his countless guest appearances on other people’s songs — like Cardi B’s no.1 hit ‘I Like It’, or the ostensibly ever-present ‘Te Bote’ — to his own wildly popular singles like ‘Chambea’, ‘Estamos Bien’, or ‘Mia’ featuring Drake, Bad Bunny steadily raises his profile without any fat to trim.

Born Benito Martinez Ocasio, he spent his childhood afternoons in Vega Baga, a modest Puerto Rican barrio, listening to reggaeton artists like Tego Calderon, Ivy Queen and Wisin Y Yandel while desperately avoiding his homework. The young Ocasio entertained his friends with joke rhymes and, at 13, began producing his own music. It wasn’t until his college years, while working as a grocery store clerk, that his friends finally convinced him to put his music on SoundCloud. It was there that DJ Luian of Hear This Music stumbled on the simple-but-stunning ‘Diles’ and plucked the cashier out of obscurity, permanently changing the Latin trap landscape.

With originators like Fuete Billete temporarily out of the limelight and rising star Anuel AA sidelined by sudden incarceration, Bad Bunny quickly occupied a vacancy in Latin trap. But unlike his peers, he unabashedly tinkers with the notion of masculinity, particularly in a genre that militantly reinforced those stereotypes. His lyrics, sung in a deep, conversational slur, blur the lines between emotionally exposed and defensively misogynistic. His behavior, the same.

In one fell swoop, last July, he chastised a nail salon in Spain for refusing him service for being a man, then threatened to impregnate the wives of those who called him gay for painting his nails. This resulted in a lengthy apology followed be the deletion of his Twitter account.

His eclectic get-up often includes flamboyant sunglasses, nail polish and dazzling coats — think a trap version of ’70s era Elton John. Though he’s recently toned-down the flamboyance of his dress just a bit, sometimes opting for more of a slacker-chic look. Though still, the Conejo is anything but standard.

As he becomes a larger force in Latin trap, many hope his charm, vulnerability and general willingness to learn from his mistakes will translate to a successful album — though many trap artists currently use albums, or mixtapes as song-dumps, often resulting in bloated, forgettable collections of songs meant to increase the perception of album sales. Bad Bunny craves longevity rather than the immediate success of inflated streaming numbers. “My only goal here is that the people will always remember my music and that they enjoy my music 10 years, 20 years from now,” he told The FADER earlier this year. “I’m ready to make songs that don’t die.”

Bad Bunny wants to challenge his audience just enough to keep them on their toes without losing them. And he’s preparing Anglo audiences for his debut, by making inroads outside of Spanish-speaking circles; his Drake collaboration ‘Mia’ landed him at no. 5 on the Hot 100.

His TV debut — a performance of ‘Estamos Bien’ on Fallon — found Bad Bunny reminding mainland audiences of the devastating impact and shameful handling of Hurricane Maria. “After one year of the hurricane…” he said, shakily as the song began, “…there’s still people without electricity in their homes. More than 3,000 people died and Trump is still in denial. But you know what? Estamos bien…” he sang as the beat dropped.

Bad Bunny’s entrance into the Anglo market hasn’t been without growing pains. His performance at the Macy’s Thanksgiving Day Parade sparked many conversations on Twitter questioning what the Spanish-singing artist was doing performing at an event dedicated to an “American” holiday. Nevermind that as a Puerto Rican, Ocasio is in fact, an American. And just shortly after, Bad Bunny again landed a moment in the spotlight, in perhaps an even more revered “American” tradition — Monday Night Football. The online chatter again veered to questions of what place a Spanish-singing artist had on American TV.

Americans like their crossover acts tokenized. They love the Ricky Martins and Shakiras who have often come with performative Latinidad. But the “spicy” Latino era is over and Bad Bunny comes as a slap in the face to those who would rather see Latinxs wearing Carmen Miranda fruit basket hats or overexerting their machismo. Bad Bunny is leading the charge to change that, and for some, it may take a while to accept.

And his response to the ignorant and racist comments about his not being an American on Thanksgiving? He posted a picture of himself and Calle 13’s Rene sharing turkey and sweet potatoes on the ’gram.

Eduardo Cepeda is a Latinx music journalist splitting time between New York and Boston. Aside from his work writing about urbano music, he is currently working on a book about his childhood heroes, At The Drive-In for UT Press. Find him on Twitter.

Olivea Kelly is an independent artist and designer. Find her on Instagram or at opk.design.

Keep up with all of FACT’s Best of 2018 coverage here.

Read next: A beginner’s guide to the history and hybridity of reggaeton