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As a rapper, Villano Antillano is armed with a fiery flow charged with cheeky wordplay and sassy one-liner quips, all helping her dismantle hate speech to boost the LGBTQ+ community. On the phone, Villana Santiago Pacheco’s self awareness and outlook is also invigorating, lending a critical perspective that partly explains why she’s so damn good at rapping.

Billboard Español spoke with the first Latin Artist on the Rise of 2023 on Monday (Jan. 23). She had just received her very first nomination for Premio Lo Nuestro’s all-genre new artist female category — a well-earned feat for years of flexing her lyrical prowess. She’s recognized next to luminary upstarts like Bad Gyal, Tokischa, and Young Miko. 

Villana’s nod follows her banner 2022: her first Billboard Global 200 and Global Excl. U.S. chart entries, viral releases, a widely viewed performance alongside Bad Bunny, and an unflinching debut album, La Sustancia X. This year, the Puerto Rican star is poised to perform at global festivals Lollapalooza Argentina and Chile, Colombia’s Estéreo Picnic and Bombastic in Spain. 

“What makes you an outstanding rapper is not about how many words you know, or whether you can rap in an academic way — it’s about how you use the language,” she explains. “It can be the language of everyday life. I use a lot of words that maybe aren’t popular like in the rest of the world, but it’s how I speak Spanish, and how it’s spoken in the Caribbean. That’s what really makes a rapper.”

She is also arguably the biggest Latin female trans artist today. Yet navigating her artistic persona while medically transitioning hasn’t been a walk in the park. “I carry it in my mind knowing that I am so much more than that label,” she says, while making mention of Latin America’s deep-rooted history with homophobia, machismo and misogyny. “I get a bit detached [from discrimination], but I don’t let it get to me … I’m a public figure, and on top of that, I’m a trans woman, and it’s inescapable that that responsibility is there. So let’s educate.”

“The trans experience is very difficult, but I think it’s incredibly magical with the access to things. It’s something that 98% of the population is never going to understand, and it’s very dangerous as well,” she continues. “It’s been a long road, there are struggles ahead, and a lot to fight. But we’re here.”

Born in the mid-‘90s in Bayamón, Puerto Rico, Villana Santiago Pacheco was consumed by music in nearly every facet of living, from cooking to cleaning. “There was always something playing,” she recalls. Her dad listened to salsa pesada “and very Caribbean things.” The very first CD she bought was Shakira’s 1998 ¿Dónde Están Los Ladrones? “I have memories of my childhood glued to a CD player, watching hours go by listening to the same songs, and seeing how the world evolved,” she muses.  

Villana came of age in an interesting time and place. The cusp of a new millennium brought the supposed doomsday of Y2K, the world wide web phenomenon, and a newly-minted, world-conquering Latin pop wave. Then there was the 2000s golden era of reggaetón — the now-globalized style with roots in New York-influenced hip-hop, Panamanian reggae en español and underground DJ mixings, igniting beyond her native Island — led by soon-to-be-legends Daddy Yankee, Don Omar, Zion & Lennox, and Wisin & Yandel. 

“Reggaetón starts to take over [locally] and becomes mainstream,” she remembers of the time. “It was musical saturation all over the place.” Villana looked up to Puerto Rico’s hometown heroine, her reggaetón royal highness, Ivy Queen. 

As a member of Gen Z, that also positioned her at the crux of the worldwide internet boom, with YouTube music videos making the rounds, rapidly exposing foreign musical works to international audiences. “The internet took over and globalization became bigger and bigger. [Local and international] music exploded, and I had access to a lot of things. I feel like I grew up in a very special time,” she reflects. 

This led her to discover the otherworldly rock en español of Buenos Aires’ Gustavo Cerati, the jazzy sophistication of Londoners Sade and Nicki Minaj’s hard-hitting rap bars. “There are artists who have accompanied me and have been fundamental to my development as a human being, and not necessarily as a musician or artist,” she says. “I consumed so much of [Cerati’s] music, and he has accompanied me at different stages of my life very strongly. I feel that I can relate very much to all of his work … I grew up listening to Sade and I think there’s an excellence in her musicianship – her elegance as a woman and everything she can make you feel; she’s never vulgar. But it’s there, super sensual, and I’m really, really fascinated by it … Nicki Minaj, she changed my life.” 

In roughly 2007, the budding artist spent countless hours devouring the overly confident verbal snaps of the Harajuku Barbie around the time of Playtime Is Over (2007) and Beam Me Up Scotty (2009). “Those [releases] completely changed the course of my trajectory as a person. I felt so much power within her music; it was like a very direct encounter with my femininity. That’s when I started writing and when I said, ‘I am going to rap’.” 

Villana first self-released music on YouTube and SoundCloud. She was formerly seen as a queer male rapper with a sly, brassy and welcoming reflection on womanhood. However, it took time for her to get into the recording studio due to lack of support in her hometown. 

“I would have broken out in Puerto Rico, but being a woman — and to a certain extent, being a maricón — with all the social impact, the marginalization, and all the discrimination that goes with it… Making a name for yourself in one of the most misogynistic, sexist, and violent countries against feminized people and women is very strong,” she says.  

“Facilitating resources was very difficult, even having access to quality recording equipment to be able to make productions — I was literally in the trenches,” continues Villana, who also co-produces all of her music. “The first person who approached me was Mixhell de León from the La Maldad collective. Basically, he gave me studio time. He said, ‘You can record here as much as you want’.”

In 2019, she released her first EP Tiranía, which followed a string of trap and rap singles. Two years later, Villano Antillano got the support of one of the biggest acts to come out of Puerto Rico: Residente, who made her the face of one of his beers. “Residente is one of the artists who has been very supportive since I started,” she says. “Residente has not only supported me, but he has also supported a lot of queer artists from Puerto Rico and implemented [their work] in his work.”

On June 8, 2022, Villano Antillano teamed up with Bizarrap for their now infamous “Bzrp Music Sessions, Vol. 51″ teamup, where onlookers saw the fiery wordsmith reintroducing herself with cool insouciance. This collab earned Villana her first entry on the Billboard charts, peaking at No. 65 on the Global 200 (Aug. 2022) and at No. 36 on the Global Excl. U.S. chart in July 2022. 

Following the viral session with the Argentine hitmaker, Villana made another global appearance — this time with today’s world’s hottest superstar, Bad Bunny, as part of a widely streamed event at one of the most important venues in Latin pop: Coliseo de Puerto Rico José Miguel Agrelot.

“It was a very special moment for me. I carry it deep in my heart,” she says of the moment. “Not only was I seen in the country, but also in every house in the country, and in Latin America! Who knows how many trans girls saw me. Maybe there was a silence among the whole family, but there was that accompaniment [amongst them]. There is a very big fear, specifically from dads. Not necessarily that they don’t want you to be the way you are, they’re trying to shield you in a way from all the hurt that’s coming. Because the world [ostracizes] people like us.” 

“Bad Bunny is an artist who has been merited as an artist with truth, and there is a lot of talk about how he implements and utilizes queer culture in all of his work,” she continues. “There’s even a scholarly class on him! I try not to dwell into it that much either, because at the end of the day I’m just a girl who got to get onstage with him, and that’s amazing.”

Name: Villana Santiago Pacheco

Age: 27

Recommended Song: “Kaleidoscópica”

Biggest Accomplishment: “To be the successful, feisty, beautiful woman I am today. That is my greatest accomplishment.” 

What’s Next: “I am really enjoying this stage. I released my album, and I feel like I’m in my motherhood stage. I’m very excited to be on the road, to be going from festival to festival, and touring. So I’m going to be working a lot, but today I’m very excited to see how far I can take it, because now I have access to things that I didn’t have before. Now I am a household name, and I have things at my disposal and resources. So, I feel that now I can get freaky with it.”