HAVANA, CUBA—We arrive before midnight. My local friend walks two blocks in front of me to avoid arousing police suspicion that he could be a straight hustler. Our destination is a bar called Habaneciendo, where the marquee advertises, “Estrellita Jaime Jimenez.” It’s early for a night out, even on a Tuesday. Eventually gay Cuban men of all ages fill the small space, talking over the romantic music videos. An hour later, the show begins with Chantal, a cross between Dolly Parton and Wonder Woman, who inspires the audience to sing along and tuck plenty of money into the front of her dress.

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