When Puerto Rican artist Sergio Vazquez was commissioned to create the concert poster for Bad Bunny’s much-anticipated March 2019 homecoming, he had no idea he’d eventually create the cover for his landmark debut album, X100PRE. It had been a pre-planned test – one which Vazquez passed – for gaining entry to the next stage. But maybe more surprising for Vazquez is that, in the process, he inadvertently inspired Benito to adopt what’s become an integral part of his persona: the third eye.

It was at last fall’s American Music Awards that Benito was widely recognized for sporting the eye, fixed onto his forehead at the pre-show red carpet and onstage during the performance of Cardi B’s “I Like It” alongside J Balvin.

But the third eye was first incorporated into the Bad Bunny aesthetic through the San Juan concert poster, where Vazquez brought the eye into the colorful and fiery mix of arrows and pathways swirling around the rapper’s image.

Bad Bunny concert poster by Sergio Vazquez. Courtesy of the artist

“In that moment, it was super ambiguous,” Vazquez says of the direction given to him by Buena Vibra, the Puerto Rican creative agency commissioned by Bad Bunny. “They wanted to bring in pinball machines, but they didn’t want to get too into that yet, so what they wanted was an intro to pinball machines in my style. So I did a sketch, and then they asked to include Bad Bunny’s face, and on that draft, that’s where the third eye was really born. That’s when everything around the third eye exploded.”

As it turns out, Bad Bunny had seen Vazquez’s work even before Buena Vibra’s suggestion. He found this out in person when he met the rapper in the Dominican Republic – at some upscale villas in nearby La Romana, he says – to discuss album artwork plans.

Vazquez has long been integrating the third eye element into his signature, peeled-apart faces with bulging eyeballs; the overall feeling is a literal representation of a mind-melting, out-of-body experience. He’d even drawn one on his portfolio: just a sketch in liquid paper on its black background. Bad Bunny, who arrived with friends via golf cart, immediately took to the visual.

Bad Bunny attends the 2018 American Music Awards at Microsoft Theater on October 9, 2018 in Los Angeles, California. Photo by Frazer Harrison/Getty Images

“It was really informal, really cool. He sits down next to me, we start talking and going through ideas. This is where the idea with the eye on black came out, because he saw my notebook; he said he’d been thinking of something like that, an eye on a black background. I’m like, ‘That’s my notebook,’” Vazquez laughs. “We started the meeting around 10 at night and stayed until about 4 a.m. He started talking about the concert, and we were tossing around ideas for that, so the meeting took off from there.”

“More people like my style right now because Bad Bunny made it OK to have that style.”

It wasn’t Vazquez’s first time illustrating for musicians. He’s a go-to collaborator for Puerto Rico’s underground music scene, from punk bands to indie fests like Bronson, even capturing a typical night at its mainstay DIY venue, El Local. Vazquez is part of the thriving community of independent illustrators and artists on the island too, showing at expos (including last fall’s Hijack!, a virtual takeover of the Museo de Arte de Puerto Rico) as well as tabling at comics and arts festivals, both locally and outside the island. And mural work, which Vazquez first got into with the collective El CoCa, where he continues to contribute, is coming up more often. Last year, he transformed walls during the popular Santurce es Ley festival and the inaugural Humacao Grita.

Through two years of full-time freelancing, he’s managed to stay true to his style, a Caribbean offshoot of R. Crumb and Rat Fink, among other wild inspirations, while seizing opportunities with corporate clients like the Compañía Cervecera de Puerto Rico and its brands Malta India and Medalla Light.

Art by Sergio Vazquez. Courtesy of the artist

“Here in Puerto Rico, it’s a bit tricky,” he says. “You have to know how to do everything; you have to be a Swiss Army knife. You have to work in styles you don’t love, and try to squeeze in your own thing within that. I feel like more people like my style right now because Bad Bunny made it OK to have that style.”

That Benito’s seal of approval has led to increased interest in his work is a bonus. But while brands often mirror trends, that’s somewhat in contrast to Bad Bunny’s actual ethos of individuality. He’s encouraged us all to be ourselves – through his idiosyncratic, goofy-cool looks, through his standout baritone, through the unexpected twists of genre delivered on X100PRE, and his general outspokenness on political and social issues. In his art, Sergio Vazquez has been steadfast in his own individuality – and maybe that’s what drew El Conejo Malo to him in the first place.

To check out more of Vazquez’s work, follow him on Instagram.