The History of Puerto Rican Drag for the Past 50 Years

SAN JUAN, Puerto Rico — Puerto Rico has been an affluent epicenter for the art of drag since the 1960s. According to Waves Ahead Executive Director Wilfred Labiosa, the bustling nightlife in areas like San Juan is largely due to drag queens and transgender performers. 

According to the Oxford English Dictionary, the word drag started to be used in the 19th century in connection to dressing up in clothes or having a persona different from your own gender. 

“Drag has become a celebrated term while keeping its transgressive power,” said RuPaul’s Drag Race All Stars Season 3 Winner and Milwaukee Native Trixie Mattel, in an interview with Them. “The word is still evolving today.” 

In the ‘60s and ‘70s, many Puerto Rican drag queens and transgender performers, like Lady Catiria, attributed to the inclusive entertainment scene. They would typically dance the Bomba, a traditional Puerto Rican dance with African roots. 

Lady Cataria was trans woman from Bayamón, Puerto Rico. Before tragically passing due to the AIDs epidemic, Lady Cataria was an icon for many Latinx queer people due to her part exhibition, part pageantry performances, according to Louie Ortiz-Fonseca from The Body: The HIV/AIDS Resource. 

“There was a dancer that was really famous and she didn’t come out as a transgender woman until much later,” said Labiosa. “Before she died she said, ‘I fooled you. I’ve been a transgender woman all of my life.’” 

Now, Puerto Rican drag queens have taken the world by storm. RuPaul’s Drag Race has featured Puerto Rican performers since the first season with queens like Nina Flowers, Vanessa Vanjie Mateo, and most recently, Alyssa Hunter.

According to Labiosa, fan-favorite Boston-queen, Jujubee can be accredited for hoisting the territory’s drag scene into the limelight. 

Around 2008, Jujubee and Labiosa were neighbors in Massachusetts, when RuPaul’s Drag Race was merely a concept. No one knew how big the franchise would become; now it has garnered 24 Emmys Awards. 

“Jujubee came with me to Puerto Rico, and we helped Nina (Flowers), and all of the rest, do their demos and send them to RuPaul,” said Labiosa. “I have to admit, Jujubee was the one who came here and grabbed all of the videos and sent them to RuPaul.” 

Nina Flowers used to perform in clubs throughout the island, varying in size throughout the years. Escandelo and Krash, which are both no longer in existence, used to be where young, up-and-coming queens would hang out. 

According to Labiosa, Spanish films used to be filmed at those clubs. Celebrities also used to frequent them.

“(Magicians) Siegfried and Roy used to hang out in Puerto Rico a lot,” said Labiosa. “They used to give funds to help form drag queen clubs.”

When one club would close, there would be transitions from one to another. Now, Kweens Klub in San Juan is the hotspot for LGBT individuals and drag performers. The club has featured many of RuPaul’s Drag Race queens, as well as local performers. Recently, Alexis Mateo hosted a show at the venue.

Alexis Mateo’s Drag Daughter Vanessa Vanjie Mateo was the first eliminated queen on RuPaul’s Drag Race Season 10. One gets a mother-daughter relationship with the drag queen that helps you get in drag for the first time, like a mentor. 

Vanessa Vanjie Mateo made a name for herself with her iconic exit line, “Miss Vanjie, Miss Vanjie, Miss. Vannnnjie.” The meme-able moment instantly hit social media and put Vanessa Vanjie Mateo’s name in lights. She was then invited back for Season 11, where she made the competition’s top four. 

Now, Miss Vanjie is one of the most followed queens on social media, with 1.4M Instagram followers and a spot on the RuPaul’s Drag Race Vegas Show. She will be coming to Milwaukee on Tuesday, July 26 for RuPaul’s Drag Race Werq the World Tour. 

Puerto Rican Queen Alyssa Hunter will also be performing in Milwaukee this summer at PrideFest on Saturday, June 4. While the San Juan queen did not make it far in RuPaul’s competition, she made sure to represent her home in Puerto Rico. 

“Puerto Rican queens?” Hunter said on the show. “Bitch, you better watch out, because Puerto Rican queens… we’re serving it, always!” 

According to Labiosa, Hunter has been to the San Juan Waves Ahead LGBT Center before appearing on RuPaul’s Drag Race. Now, queens like Angelina Bee and other queens from the Bee family come to the center to do make-up sessions for the LGBT Senior Community. 

“They [the Bee family] are appearing on the counterpart to RuPaul’s show in Puerto Rico on Latino Telemundo,” said Labiosa. “There’s a lot of competition for RuPaul. RuPaul is way up there, but they are trying different, but similar competitions.”

According to Labiosa, there have been a lot of influences on the straight community. There are comedians, straight and gay, who dress up in drag to do their performances. Contrary to the US, drag is reaching more than just niche, LGBT audiences in Puerto Rico.