Chartbreaker: Guaynaa Thought He'd Study Engineering, Then Landed a Stateside Hit

“My influences started from a young age,” the 27-year-old tells Billboard. “My grandparents were troubadours, doing typical music on the island that you improvise. On Christmas, we’d have huge parties and all of us would sing and play instruments, and we’d listen to all different types of music: merengue, Elvis Crespo, Charlie Zaa, salsa, everything.”

While his family introduced him to a wide range of styles, Santiago found out in middle school that he had a knack for freestyling. He’d mess around between classes and perform for groups of his friends. “I’d go on for three minutes without stopping,” he recalls, “and I’d rap about things that probably aren’t too nice to repeat, but I had the delivery, I had the skills.” 

He even entered a few local rap competitions, where he first got his nickname “guayna,” a Puerto Rican slang word for wealthy, high-class snobs. Santiago wasn’t actually from a well-to-do family, but he had funny, extroverted personality and he’d wear puka shell necklaces and collared shirts as a joke. The name stuck, and he’s built it into a full persona as a facetious prepster who isn’t afraid to poke fun at himself. 

Although his rapping has always come with a comedic side, Santiago struck a more serious balance in 2017 after seeing the devastation that Hurricane Maria left on his island. “I felt indignation for all Puerto Ricans, for the lack of power, for the lack of food, for the death toll,” he said. “I saw drowned people, cars turned over, businesses destroyed.”

He poured all of his feelings into a subversive two-minute rap called “Maria.” “I was conscious that I was walking a really fine line because of my particular concept. It had to be fun, but not too fun, because if people just consider you a clown, it’s not going to amuse anyone. I had to do it right, but I knew I could do it,” he says.

The song had local appeal -- the video currently boasts more than 1 million views -- and the reaction encouraged Santiago to churn out more music. In December, he was in the studio and he remembers thinking, “We need a dirty perreo from back in the day.” Within 20 minutes, he’d written the salacious, tongue-in-cheek lyrics to a beat that Miami producer Kino had created, inspired by Dominican rapper N-Fasis’ “Lento.”

“It was actually funny because of all of the acoustics -- we had to turn off the fan because the mic was picking up the sound, and there was a dog that kept coming into the studio and barking,” he remembers. But when it was finished, a friend of his in the studio turned to him and told him what he already suspected: “That’s a banger.”

Fans in Puerto Rico quickly confirmed that they thought so, too. “It was blasting in all of the cars, it was in all the clubs, and on the radio,” he recalls. From there, “ReBoTa” broadened out to other parts of Latin America. “It was just something really crazy -- the song connected hard and the world made it big.” 

The sheer force of the “ReBoTa” led Santiago to meet with Universal Music Latino and Republic Records, who signed him to a joint deal in June. Becky G, Farruko, Nicky Jam, and Sech jumped on the remix in July, and by September, the track had a 4x-multi-platinum RIAA Latin certification.

In fact, “ReBoTa” was so big that it made a fan out of Bad Bunny, who invited Guaynaa to perform the track onstage with him during a concert in Puerto Rico’s biggest indoor arena. Moments like these have served as validation for Santiago after the different careers he’s left behind: “I sacrificed everything,” he admits, “and I wondered if I’d missed an opportunity.” 

In the last few months, Santiago has been solidifying his somewhat satirical style with visuals for “Buyaka,” which he brainstormed as a way to flip the script on how women are sexualized in videos, and “Chicharrón,” conceptualized as a funeral for old-school reggaetón. Lately, he’s been working with Visitante, the pioneering producer and member of Calle 13, to push the limits on his ideas and to experiment with weirder and bolder sounds. He wants to make an album that explores styles from across the world, from pop to flamenco. He has one promise for his fans: his upcoming music is “not going to be expected.”

A version of this article originally appeared in the Oct. 19 issue of Billboard.