What Are You Looking At?

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.

It takes a discerning eye and confidence to entrust your creative project to a teenager you just met at the club. But Madonna was a fellow dancer—she’d gone to the University of Michigan on a full dance scholarship before dropping out to perform in New York—and had a dancer’s appreciation for a new movement vocabulary. If it was a risk, it paid off: the video, directed by David Fincher and inspired by Isaac Julien’s Looking for Langston, took voguing mainstream in a way earlier attempts, like Malcolm McLaren’s “Deep in Vogue,” had not. Days before the tour began, Madonna took a chance on another young artist, a twenty-four-year-old filmmaker named Alek Keshishian who’d made some music videos for Bobby Brown. Madonna called him up and said she had this HBO special, would he be interested in doing it? She imagined some black-and-white footage interspersed between the numbers—a little Nouvelle Vague, a little cinema verité. The tour was beginning in Japan in four days. If he was free, he could give it a try.

The footage Keshishian shot in Japan became the basis of Truth or Dare. With the healthy self-seriousness of a recent Harvard graduate, he told her he would need carte blanche to shoot whatever he wanted, and amazingly she agreed: everything but business meetings was fair game. He tested her word almost immediately, standing by to film her getting a chiropractic adjustment backstage. She’s sitting on the end of a massage table in her synthetic blonde high ponytail, yanking a shoe off her foot. Her voice is high and hoarse: “You’re not filming me getting an adjustment, I won’t be able to relax, I’m serious,” she says. “Alek, no. No way.”

“We talked about this in LA,” he mumbles.

She pulls down her cutoffs and smiles. “About me getting an adjustment?”

Her chiropractor stands waiting at the far end of the table. Her massage therapist, Julie, suggests she tune it out. Madonna gives her a look and says, “Julie, shut up. Don’t tell me to tune it out.” She lies back on the massage table. The chiropractor cups her chin, says, “drop this shoulder,” and cranks.

Keshishian shot ten hours of film on the trip to Japan, most of it interviews with the male backup dancers in their beds in the morning. Also present was a producer who had worked on Rattle and Hum, the 1988 U2 documentary and infamous commercial flop. Keshishian told Film Stage that the producer said he’d got better material in three days than they’d got in all of Rattle and Hum. Back in LA, Keshishian played the footage for Madonna and insisted they had more than a special. “This is like a Fellini film,” he said. (That twenty-four-year-old inspiration again.) “You have the craziest characters around you and you’re like a mother hen.” Against the counsel of others, she agreed, and gave him final cut. The only rule, besides no business meetings, was that she wouldn’t do anything twice. If he missed a moment, he missed it.

Sam McKinniss, Madonna, 2018, oil and acrylic on canvas, 16 x 12". Courtesy the artist and Almine Rech
Sam McKinniss, Madonna, 2018, oil and acrylic on canvas, 16 x 12". Courtesy the artist and Almine Rech

The portrait that emerged is brassy, magnetic, irreverent, smart. Truth or Dare showed Madonna as a performer on an elemental level, a ham who cracks wise and won’t shut up. Somehow, she is never annoying; either she knows when to pull back or the editor does. It’s one long screen test, and the camera loves her from every angle: Sitting on the couch in a hotel room in a shower cap, slurping soup on the phone with her dad. Telling stories from the makeup chair about getting finger-banged by her childhood best friend. Sticking her tongue out and dousing her throat with throat spray. Standing in a pre-show prayer circle, head bowed and eyes closed, after facing threat of arrest for “lewd and obscene behavior.” (“Dear Lord, this is our last night in Toronto. The fascist state of Toronto.”) Standing on a chair at her assistant Melissa’s birthday dinner, reciting, in a New York accent, a poem in anapestic tetrameter that rhymes until the last line: “If you ever leave me / I’m gonna fucking kill myself.” Or—my favorite—stepping out of a limousine with voiceover from another interview: “I had a dream last night that Gorbachev came to my show. My first reaction was that Warren Beatty was gonna be so jealous that I got to meet him first. Anyway, it was a good dream.”

Onstage, her energy is explosive. She’s jumping, flexing, kicking, strutting, thrusting, pirouetting, and running in place. She’s fondling her Gaultier cone bra, grabbing her crotch. Her body is insane, tiny and muscular and somehow still soft. Offstage, her boundaries are, by today’s standards, abominable, especially for a boss. “Does Jose love me more than I love him?” she croaks, hanging off his arm in a hotel. Luis says yes, that Jose comes back from rehearsal and pumps “Lucky Star” in his room—that’s how much he loves her. Madonna drops to the floor and puts her loving cheek on his foot. “Don’t ever leave me!” she mock cries, and he looks a little bashful. This is a tame example. Somewhere in Europe, at an outdoor dining table, another dancer initiates a game of truth or dare.

CARLTON WILBORN [dancer]: Truth or dare, Madonna?

NIKI HARIS [backup vocals]: Wanna play?

MADONNA: Right now? I want to ask you. [To Carlton] Have you ever been fucked up
the ass?

NIKI: Well, you gotta ask him what he wants first.

MADONNA: Truth or dare?


NIKI: [Laughing] You fucked up!

MADONNA: OK. Unzip your pants and take your dick out right now.

NIKI: Aaah-hah, you have to do it!

CARLTON: No way!


NIKI: Way. Dare. Come on.

KEVIN STEA [dancer]: That’s what she told you to do.

At this point Carlton stands up and Madonna shields the camera with a fan. “I’m afraid to look,” she says, and squints her eyes. He unzips and she looks, forgetting the fan. For a split second you can see his penis.

MADONNA: [Squealing, stomping]

CARLTON: [Laughs]

MADONNA: It’s fucking blue!

Was it all an act? Yes and no. The fact that Keshishian was “always around” meant that people got “lulled to a certain degree” and stopped “performing for the camera,” he told Paper. Glimpses of vulnerability seem to back his claim, including a moment in the same game of truth or dare when Donna De Lory, Madonna’s other backup singer, asks who has been the love of her life, “in your whole life.” “My whole life?” Madonna says, and for the first time her face looks deflated. “Sean [Penn]. Sean.” But at least one person was never lulled: Warren Beatty. In the middle of her tour, Madonna gets a vocal-cord infection and has to stop at her apartment in New York. Beatty is over, and so is Keshishian, filming while a doctor wraps her tongue in gauze and holds it down while she says aah. “This is crazy,” says Beatty, sitting with his legs crossed and his sunglasses on. One hand is on his temple. “Nobody talks about this on film?”

“Talks about what?” says Madonna. The doctor has released her tongue.

“The insanity of doing this all on a documentary.”


BEATTY: This is a serious matter, your throat, yes?

MADONNA: Why should I stop here?

BEATTY: But does anyone say it?

MADONNA: Who’s anyone?

BEATTY: Anyone that comes into this insane atmosphere. You realize they all feel it when they come into this atmosphere. When they come into your dressing room, when they come wherever you are, they feel crazy. Now, do they talk about it?

MADONNA: [Puts her head in her hands] No, they accept it.

BEATTY: [Adjusts sunglasses] Why don’t they talk about it?

MADONNA: ’Cause.

BEATTY: You want to think about that, don’t you?

MADONNA: No, I don’t. [Smiles at the doctor] Let’s get back to my throat.

There’s a jump cut, and Madonna is no longer speaking. Beatty looks at the camera and says, sarcastically, “There’s nothing to say off camera. Why would you say something if it’s off camera? What point is there existing?”

But there were, as always, layers to every performance. The 2016 documentary Strike a Pose, which revisits the backup dancers from Truth or Dare, revealed that three of the seven dancers were HIV-positive on the tour, a fact they kept hidden from each other and from Madonna. Another three were gay but not “out-out.” Truth or Dare was remembered by a generation of young people for depicting gay men “being themselves” and being accepted; it inspired them to come out to their parents. But the dancers were faking it, too. Wilborn recalls the “internal storm” of “faking that you’re strong, faking that you’re confident, faking that you think you look good. Faking that you believe people really care about you. Faking. Almost all of it.” The French kiss Salim “Slam” Gauwloos gives Gabriel Trupin on a dare was a watershed moment in American culture, one that revealed the gulf between the gay and straight worlds. (“I grew up in Michigan on a farm,” one handsome man-on-the-street interviewee in Strike a Pose says. “So when I saw the gay kiss, it was the first time I’d ever seen that, and it was very liberating for me.”) It’s a beautiful and deeply hot kiss, and something in their faces makes it feel like the consummation of a crush. But Trupin didn’t want the scene included. He was twenty, and according to his mother, “He wasn’t there yet, he wasn’t ready.” Madonna refused to cut the scene, saying he was ashamed and he needed to get over it. He sued her for forced outing and they settled out of court. She was wrong, in retrospect, but also right. Trupin died of aids in 1995, before he could see the difference it made.

It’s hard not to feel that a movie like Truth or Dare couldn’t be filmed today. Recent documentaries about mega-pop-stars are all so brand-safe by comparison, so self-conscious and controlled. There is nothing off-the-cuff about Ariana Grande: Excuse Me, I Love You (2020), or Miss Americana (2020), or Homecoming (2019), or Katy Perry: Part of Me (2012). They have their tender moments, usually confessions of exhaustion, like Beyoncé saying, “I will never push myself that far again” or Perry’s face transforming from full desolation to a showbiz smile as a hydraulic riser lifts her to the stage. What are they leaving out, consigning to the digital trash can? Maybe there are gems on the level of Truth or Dare waiting to be surfaced by some future estate. More likely, there are hours and hours of a celebrity looking at her phone, refining her image in post.

Dayna Tortorici is a writer and the coeditor of n+1.