Dayna Tortorici in Bookforum:
WHEN PEOPLE TALK ABOUT TRUTH OR DARE, the notorious 1991 documentary about Madonna’s Blond Ambition tour, they tend to mention the same handful of scenes. The gay kiss. Madonna deep-throating a bottle of Vichy Catalan (not Evian, as often misremembered). Kevin Costner calling the show “neat” and Madonna making a puking gesture. Are these the best scenes in the film? No, but they passed for scandal in 1991 and so they made an impression. In retrospect they feel a little try-hard, a little overhyped, but that’s because we’re watching from the world Madonna made. With the distance of thirty years, it’s easier to appreciate everything else. Her intense relationship with her dancers. The range of personality on display. Above all there’s the serendipity of timing and access. Few pop stars of Madonna’s magnitude would give a filmmaker the free hand she gave director Alek Keshishian in 1991, including the Madonna of 2021. Few documentarians would have as much as he did to show for it.
Truth or Dare caught Madonna at the height of her powers. She was thirty-two, divorced, and recently denounced by the Vatican for “Like a Prayer.” She was also in a new phase, marked by a blend of ambition and unguardedness that she would never quite experience again. When filming began, in 1990, she had just finished her performance in Warren Beatty’s Dick Tracy and recorded an album, I’m Breathless, tied to the film. Among the album’s tricky Sondheim numbers was a club track she cowrote with Shep Pettibone called “Vogue.” “Vogue” had little to do with Dick Tracy—it was inspired by the Harlem ballroom scene that Madonna had caught glimpses of in downtown clubs—but Beatty was now her boyfriend, and a single would give his movie a boost; the spoken-word interlude name-checking Hollywood icons (“Lauren, Katharine, Lana, too / Bette Davis we love you”) would suffice for thematic unity. One night at the Sound Factory, Madonna’s friend Debi Mazar introduced her to a young dancer from the House of Xtravaganza, Jose Gutierez, who was known to be a talented voguer. Madonna had him audition on the spot, persuading him to swap pants with her bodyguard so he could access his full range of motion. She then hired him and another young Xtrava, Luis Camacho, to choreograph and perform in the “Vogue” video and to join her as backup dancers on the Blond Ambition tour. At the time, Gutierez needed his mother’s written permission to go; he was still underage.