The performer’s mix of masculine and feminine style evokes a long history of Puerto Rican artists using drag as political protest.
By Daniel Villarreal
Image: Bad Bunny in drag in his music video for “Yo Perreo Solo” (“I Twerk Alone”) | YouTube screenshot (Queerty)
Immediately after Puerto Rican reggaeton artist Bad Bunny was announced as the halftime show performer for the 2026 Super Bowl, right-wingers began trying to “cancel” the cis-het ally by pointing out his refusal to sing in English and his past performances in drag.
Bad Bunny — who grew up in a lower-middle-class barrio near Puerto Rico’s small coastal city of Vega Baja — has always subverted gender norms and expressed his queer-friendly political identity by incorporating masculine and feminine elements into his flashy fashions (which have included bright colors, oversized garments, and eye-catching accessories). But five of his public appearances specifically made headlines for their gender-bending appeal.
Here’s a quick look at these five instances, along with a brief exploration of how they reflect the long queer history of Puerto Rico’s drag and gender-bending performers, and how both have sought to express and transcend the island territory’s complex political relationship with the United States.
Fashion activism
During his February 2020 performance on The Tonight Show, Bad Bunny performed while wearing a large pink blazer and black skirt.
Later on in the show, he revealed a t-shirt that said, “Mataron a Alexa, no a un hombre con falda,” (“They killed Alexa, not a man in a skirt”). The t-shirt referenced the murder of Alexa Negrón Luciano, a homeless transgender woman in Puerto Rico, who the police report misgendered as a “man dressed in a black skirt.”
A red leather minidress and flawless wig
The music video for the song “Yo Perreo Sola” (“I Twerk Alone”) — released in March 2020 — featured Bad Bunny in a red leather minidress and flawless wig, portraying a sexy woman who really just wants to be left alone to dance by herself at a club.
Later on in the video, he dresses as a long-haired woman whose bright floral outfit accentuates her breasts and buttocks.
