The Madonna Project: Bonus. “Truth or Dare” (1991)


When I started this column, I promised myself that I wasn’t going to get too involved with discussing Madonna’s live performances. This was because of my Tom Waits Project from 2019 where things got unruly with live recordings that ultimately gave me nothing to say about his brilliance. Considering that Madonna looks like she releases a new concert documentary every time she steps out the door now, it would be even worse if I had to cover every one of them, trying to find the vague differences from the “MDNA” and “Madame X” eras. I will ignorantly say now that there isn’t that much to warrant two whole pieces, so I put the kibosh on that right away.

But the more that I began to look at her career at large, the more that one concert documentary, in particular, came up: Truth or Dare (1991). This wasn’t just another expedition to see her do this dazzling choreography with fantastic set changes. This was an essential tool in understanding the Madonna mythos, which was coming at the peak of her career. In 1989 she released one of her most personal albums with “Like a Prayer,” and has produced an Oscar-winning song for Dick Tracy (1990), there wasn’t a better time to be her. What followed was a moment in time while touring internationally on The Blond Ambition Tour, giving audiences at home a chance to see her as something more complicated and human. 

Considering that she had also recently brought ballroom culture to the mainstream with her single “Vogue,” she was already doing plenty to change the public’s conversation around LGBT representation. After 29 years, there are still reports that the way that Truth or Dare normalizes its gay back-up dancers helped a lot of people accept their sexuality. Not only that, but it helped to paint Madonna as a more complex figure, discussing a salacious relationship with comedian Sandra Bernhardt, reflecting someone who took queer culture under her wing and called the dancers her children. Given that it was the highest-grossing documentary up to that point, the impact could not be understated.

The original plan for Truth or Dare was to have David Fincher, who directed “Vogue,” film The Blond Ambition Tour. Considering that it had elaborate set changes and these dazzling set designs, it made sense to just take in the experience. In a time where she was dating Warren Beatty and getting banned by The Pope, who wouldn’t want to see what the world looked like from her perspective? Well… Fincher dropped out and Alex Keshishian stepped in following a student film that Madonna was impressed by called Wuthering Heights. She saw something in him and demanded that he rent every concert film in order to understand how to make it work.

The story goes that Keshishian rented them, but never actually watched them. He cited the U2 concert documentary Rattle and Hum (1988) as a way of how not to do it given its bad box office. He thought that it would be more exciting to do it by emphasizing the backstage shenanigans, cutting the concert sequences down to minimal appearances. This was to be a pop star version of a Federico Fellini movie, with most of it shot in black-and-white to differentiate between the public (color) and private (black-and-white) life of Madonna. Once she saw part of the 200 hours of footage, she understood Keshishian’s vision and allowed him to go through with it.


Cameras would be everywhere. There’s even a scene where Madonna would be talking to Beatty about how she’s making “a home movie.” Like most people at the time, he didn’t understand the concept of having a camera in every corner of the room, capturing the “candid” conversations. Where was the appeal in watching people randomly talk about their personal lives? Given that Truth or Dare was praised for its frank depiction of gay men having normal conversations, there was something more than watching Madonna walk around. This was a chance to demystify the creative process, reflecting it as something akin to a barely held-together production.

The Blond Ambition Tour was by no means a financial failure, but it’s those moments where the documentary is at its most interesting. What this ultimately does is reflect the effort that Madonna will go to entertain a crowd. She is there personally regretting the presence of rain while in Japan, getting frustrated by microphones shorting out, and even the fact that her voice goes out. To watch her in an appointment with her doctor reflects how vulnerable she is on a deep level. She needs those vocal cords to entertain thousands. The world is relying on her, and it creates this pressure to be a perfectionist, barely keeping her back-up dancers from breaking out into petty fights. She has to cancel shows because of her voice, and you can tell that it bothers her.

Or does it? That’s the thing about Truth or Dare. In a lot of ways it was the prototype for the modern reality series, showing reality not as it is but what it’s like when a camera is in your face. At its best, this plays like a D.A. Pennebaker documentary capturing moments that you’d never see otherwise. Keshishian’s eye is constantly moving around and looking for the next memorable moment. The only issue is that so much of this is an artistic choice that certain moments feel choreographed, or at least prodded into existence. Is Madonna serious when she discusses sleeping with women? 

If the film didn’t look so polished and calculated, it would be easier to believe small things like this. Given that scenes like the notorious graveyard visit to her mother felt like a music video (set to “Till Death Do Us Part”), it was hard to know how much of a front Madonna was putting up. After all, she was at her peak gimmickry. Dick Tracy found her releasing a goofy album in character. She was on the verge of releasing the controversial book “Sex,” and everything else felt like it existed in a manner meant to get a reaction. How sincere and genuine was she?

If you buy into the sincerity, it all kind of works at painting this hardworking performer who gets caught up in every small issue. In one extended scene, she is encouraged not to perform “Like a Virgin” at a stop in Toronto, Canada because it’s seen as pornographic and will get her arrested. Keshishian paints it like Madonna as an altruistic hero, needing to stick to her vision that involves such things as writhing around on a bed, running her hand along the front of her covered pelvis, and then humping the bed like Linda Blair in The Exorcist (1973). Madonna can’t sacrifice her vision and makes a big deal about it. She will cancel the show if she can’t hump that motherloving bed. Oh, how she longs to hump that bed in front of a crowd, cheering her on and saying “Ay, you’re good at humping that bed.”


This is an act of defiance, of self-expression and art. It also goes on, and you’re wondering if she will go through with it. As it plays out, there’s some joy in watching her perform these acts. Keshishian can’t let it play out naturally, instead giving us abrupt cuts to her pelvis. Still, the most interesting part of the moment is how you can hear the crowd sing along to her slowed-down version, reflecting just how much control she has at this moment. Then she humps that bed, and boy does the crowd love it. Cut to the next day where a news anchor suggests that the concert ended without scandal since nobody found anything wrong with it. Madonna wins, we all go to the next city and see adoring fans waiting to watch an American hump a bed.

I understand that this is all part of Madonna’s appeal, but it becomes abundantly clear how much of her act is about pushing boundaries. The 1980s were a conservative time, so sexual gratification in a woman wasn’t as socially accepted. Madonna doing suggestive poses as scantily clad men surround her and she seduces female dancers is what draws you to her. 

However, there’s so much about this that feels redundant once you realize that the whole thing eventually plays like Madonna humping a bed. There is arguably no artistic expression in this act that couldn’t be altered, but because of her ego, we need to have everything to raise as many eyebrows as possible. She is a spectacle, a performer who revels in questioning the public’s understanding of sex. Some of it makes sense, especially in the more playful Cabaret (1972)-esque moments where the pageantry compliments the other themes of her work, like religion. If this documentary had any more focus on Madonna’s personal and religious life, it might have made her more sympathetic and interesting.

Instead, we’re put into nonstop moments that feel like Madonna humping a bed. As much as you can find endearment in her serving as a mother figure to her queer back-up dancers, the moments that ultimately feel like she wants you to be taken away with are sensuous in nature. She seems to be moments away from kissing people. She encourages people to strip and jump into bed with her. She fellates an Evian bottle. She even goes so far as to flirt with the married Antonio Banderas at filmmaker Pedro Almodovar’s house. Even then, the funniest part of the Banderas scene isn’t the kink, but Madonna proudly declaring “and I never saw him again,” not realizing that they were only a few years off from starring in Evita (1996) together. Still, if we’re not thinking of Madonna’s work ethic, we’re just waiting for her to hump another proverbial bed. This is especially amusing when you consider that she disapproved of the international version being called In Bed With Madonna.

Subtle

On the surface, I get the appeal of Truth or Dare. Artistically it is masterful and makes the dramatic inner life of Madonna far more interesting than you’d expect. To judge her solely for her music is to do yourself a disservice. To fully understand her vision, you need to look at her as a public figure, and this is a great starting point. So much of her essence as a performer comes through not only in the story but the implicit details underneath. It’s in how she longs to be the center of attention at every turn. If you ever needed to answer the question “What makes Madonna special?” you almost don’t need to listen to an album. You just need to see crowd adoring outside a window in Truth or Dare as she sits alone, preparing for the day ahead.

Another reason that Truth or Dare feels essential to cover while every other concert documentary doesn’t is because of its cultural impact. Besides being the highest-grossing documentary until Bowling for Columbine (2002), it helped to normalize the conversation around queer representation in media. It also leads to so many parodies, including a memorable bit involving Mike Myers and Dana Carvey on Saturday Night Live. Beyond that, it made the idea of reality and celebrity more transparent, asking us to wonder what was real from our performers. Keshishian has gone on to collaborate with contemporary pop stars like Selena Gomez due to her love of Truth or Dare. Even in recent works like Beyoncé’s Homecoming (2019), you can see this candid and artistic style used to reflect an artist’s full career.

For me, Truth or Dare is more groundbreaking for what it represents than ultimately what it does. I am intrigued by these moments that find performers being human, reacting to the world around them from the comfort of their isolated spots. However, amid a story full of fascinating looks into the queer lifestyle, there is Madonna doing things that range from fun and insightful to things more calculated. Much like her humping a bed in Canada, some of it lacks a deeper resonance other than to get a rise out of people. What is real and artificial? It’s hard to say. 

Still, if you thought that her raging hormones were too much here, just know that in the next few years we’d get the book “Sex,” as well as the album “Erotica.” While I don’t intend to write a review on “Sex,” do know that I’m about to look at the album that opens with “If I'm in charge and I treat you like a child/Will you let yourself go wild/Let my mouth go where it wants to.” (“Erotica”) I know that it’s been a journey since “Hanky Panky” of dealing with Madonna’s eroticism growing more and more obvious, but I’m sure by the end of next week you’ll understand why I see it all as one long bed humping. 

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