When John Holiday was growing up in Texas, he went to church every single day. His grandmother—he calls her Big Mama—encouraged Holiday and his siblings to sing, but, one by one, as they grew up, they stopped, except for Holiday, who went on to become a professional countertenor—a male singer whose vocal range reaches the same high-flying notes typically occupied by female singers—with a thriving operatic career. Two days before his performance in Crypt Sessions, a series of intimate concerts held in the stone chamber beneath the Church of the Intercession, in Harlem, he visited the space to speak to The New Yorker.