We played a game of truth or dare to celebrate the 30th anniversary of Madonna's iconic documentary

Anne T. Donahue and Peter Knegt each write regular columns for CBC Arts, and they decided to come together to take some time to celebrate, just one day out of life ... the 30th anniversary of Madonna: Truth or Dare.

Contains strong language.

Peter Knegt: So, Anne, we "meet" again, this time to honour the 30th anniversary of certainly one of the influential — and in my opinion, one of the very best — music documentaries of all time: Madonna: Truth or Dare, or as it was much more known outside of North America, In Bed With Madonna. I hate myself already for what I'm about to suggest but I think we might have to format this conversation in the form of ... a game? 

Anne T. Donahue: So help me Peter if that game is "truth or dare."

PK: It is.

ATD: Ok fine. But you're going first and I'm never picking dare.

PK: That is absolutely fair. And I pick truth.

ATD: You mentioned that Madonna's Truth or Dare is one of the best and most influential documentaries ever made. Truth: What aspects of it do you see as being particularly iconic?

PK: Honestly, the entire thing is wildly iconic. I rewatched it last night for like the 40th time and something that just really stands out to me is how much fun Madonna seems to be having making it. All these recent music "docs" — Taylor, Katy, Shawn, Gaga, Demi — go so hard on emphasizing the struggle of their subject in terms of being famous. But Madonna — certainly 1991 Madonna, at least (through definitely not 2021 Madonna!) — thrived under a spotlight, and Truth or Dare so masterfully documents that. And like, this movie was a massive hit in a way that's completely unparalleled. It held the record for the highest-grossing documentary of all time for eleven years, until 2002's Bowling For Columbine surpassed it. 

But iconic aspects, let me go specific and narrow it down to three moments:

1. The entire Toronto part. I mean, obviously I'm biased given that I am typing this from whatever's left of Toronto, and with how the last few months have gone here, I have never quite felt so embarrassed to live here. So watching Madonna oh-so-publicly shit on the "fascist state of Toronto" when the cops threaten to arrest her at her Skydome show if she doesn't take out a part where she simulates masturbation (she doesn't take it out, and they don't arrest her) felt particularly emblematic to me right now.

2. When Sandra Bernhard visits Madonna on tour in Europe and they sit in her hotel room and just talk shit about people they're sleeping with. To have this intimate access to one of the most iconic friendships of all time is just such a gift.

3. The Pedro Almodovar/Antonio Banderas bit, which is so much more juicy now that we've heard Almodovar's side of the story (that Madonna treated he and Banderas like "simpletons"). Basically, Almodovar throws a party for Madonna in Madrid, which Madonna attends hell-bent on sleeping with Banderas. Banderas shows up with his unimpressed wife, and then things end with Madonna saying to the camera that she'll never see Banderas again and didn't really think he was a good actor anyway. The fact that five years later they'd make Evita together is all the more wild given that the following sequence in the film has Madonna going out on a balcony to greet her fans below just like Eva Peron!

Your turn. Since I assume you'll pick truth: When was the first time you saw Madonna: Truth or Dare?

ATD: In its entirety? Yesterday afternoon at approximately 1pm. But it isn't my fault! I was six when it came out in theatres, and outside of catching clips of it or seeing it featured as part of bigger pop culture discussions, I didn't really get the chance. I'm much more fluent in Madonna in A League of Their Own. Am I fired?

PK: Never. 

ATD: Perfect, because I refuse to leave. Now my turn! Watching this made me begin to better understand Madonna's hype as an artist. Also, it made me realize just how tiny she is. (Why did I always think she was really tall?) How did Truth or Dare change your relationship to Madonna? Or was it the movie that kick-started your appreciation for her?

I guess this is a truth-or-dare way of asking you to chicken-or-egg your fandom.

PK: My Madonna appreciation was birthed at a high school dance circa 1997 when my friends requested "Like a Prayer" — which I had never even heard of before that — and then we all danced to it. I vividly remember my 13-year-old self just screaming as it came to its glorious, gospel-fuelled final act: "This is the greatest song of all time!"

The movie came a year or so later, and I was floored by it — in part because of just how bold she is in it (making fun of Kevin Costner on this scale!) but also because of how unapologetically gay the film is in terms of all the out dancers whose stories the movie incorporates quite heavily. I just remember thinking, "Ok, this is my queen." And also being kind of jealous that I'd been too young to really experience this late 1980s/early 1990s era of Madonna, which was clearly the peak of her just being so exciting. I gladly got to be a part of the Ray of Light/Music/Confessions era in my teens and early 20s but I'm fairly certain it wasn't quite the same thing.

What about you? When — and how — were you introduced to Madonna?

ATD: So, like Madonna herself, I was raised Catholic and went to Catholic school. And that means everything I heard about her in childhood was largely about how terrible and disgraceful she was. But I remember it taking until the release of Ray Of Light when I was about 13 to like her as an artist outside of her standard hits. I also used her 1999 MuchMusic appearance as a way to try and show my parents how much Madonna had changed and grown since "Like A Prayer." I realize now that they didn't care one way or another, and probably never really did.

Oh, but! My aunt loved — loves — Madonna! And I have a really fond memory of her and my other aunt letting me play with their makeup while they grooved to early Madonna. I was three or four, but I remember thinking, "This is so grown-up!"

Even now, there's something about early and earlier Madonna that makes me think, "Holy shit!" You see that onstage and you see it in the behind-the-scenes footage of her being an incredibly intentional performer. You also see it in the way she's obviously rebelling against Catholicism through the imagery she opts for and the way she blends overt sexuality with religious symbols. And the idea of performance also expands into those moments where we're seeing her at the hotel or with her dancers. What moments do you think aren't performances? Personally, I cringed so hard when her childhood hero corners Madge to ask her to be the godmother of her unborn child. You could tell Madonna wasn't in control, and I could feel just how much of a nightmare that probably was — for everybody.

PK: I mean, the entire movie is a performance, whether she's on stage or not. What does her then boyfriend Warren Beatty say about her at one point in it? "She doesn't want to live off-camera, much less talk. There's nothing to say off-camera." But somehow that doesn't really matter? Madonna was just so good at making her performance seem authentic, which is something I don't think anyone else has ever come close to achieving on that level. Like Lady Gaga or Taylor Swift, for example — it's so hard for them not to seem fake in their documentaries or in interviews. Even though it's obviously all a masterful construction by Madonna herself, Truth or Dare almost always feels raw and honest ... and also somehow never feels cynical. Which I'll admit is a bit hard to watch now that Madonna has descended into whatever her Instagram suggests she has. Which leads me to your next truth: what is your current impression of Ms. Ciccone?

ATD: Oh man. It's so complicated. Isn't that all of our impressions of her at this point? I saw Truth or Dare and felt like I really understood her and really understood what was expected of her and how hard that must've been. So I see the brilliance and I have empathy and I admire how nurturing she can be. But then I see the recent publicity stunts on social media, and the cultural appropriation, and the way she simply refuses to listen and learn, as if her years in the business buys her a coat of Teflon. (It doesn't!) And then you hear about how she doesn't like people to look her in the eye at film festivals. And it's like, "Lady, what are you doing?" She's done so much good work over the course of her career. But also: what the fuck? Why does she seem to get off on conflating intentional ignorance with being shocking? You can shock a shit-ton of people without purposely offending.

I can't be alone in this, can I? I think that's what really got to me while watching the doc. I could see exactly how herself Madonna really was. But I could also see how good she is and was at courting controversy and controlling her own image. And that made me wonder if anybody really knows who Madonna is — including Madonna.

PK: My feeling is that Madonna definitely knew who Madonna was at the time of Truth or Dare. And she also knew what Madonna she needed to project to the public, and was extremely good at doing so. Today I feel neither is the case? But I try to not let it totally destroy my entire perception of her. She's still around, still making music even (her last album was even sometimes not bad!). She made it through ... the wilderness, more or less. You think about how many of her contemporaries either got totally destroyed by their fame or tragically passed (or both) and you at least have to hand it to her just for surviving. Even if that's led her to currently living in some castle in Portugal making unhinged Instagram videos of her in milk baths or whatever.

ATD: I will say that Truth or Dare made fame seem like an absolute nightmare to me. I mean, I've always known it was or could be, but this made being famous seem particularly lonely and demanding and full of the worst type of pressure. And honestly, I think that's the most authentic thing about it: this documentary, whether intentional or not, made being famous seem so sensational that it necessitated hours and hours of footage. And that's just too sensational for me. That can't be healthy for the heart or mind, you know?

PK: It definitely cannot. But ok, let's end things on a fun note. Fuck, marry, kill: Warren Beatty, Antonio Banderas and Kevin Costner, at the time of Truth or Dare.

ATD: This is such an exciting question, and I'm ready to get serious about it. I'd never marry Warren Beatty because I'm not secure enough to deal with his then-reputation. So we'd obviously have to share one-too-many nights of passion because he is beautiful. I'd marry Antonio Banderas because I imagine it would be romantic and wonderful and I loved him as Puss 'N Boots. And I can't kill Kevin Costner because he just seems so gentle and sweet. But his mullet prevents me from seeing him as anything other than like, someone who would've lived on my street in the '80s. I don't mind that he used the word "neat," but I do mind that a freakish number of people have likened my dad-as-a-young-person as a Costner doppelganger, which has forever ruined everything for everybody.

So now your turn! FMK: Warren, Antonio or Kevin? And did you ever read about how a few years ago, Madonna apologized to Kevin onstage when he was with his daughters in the crowd at one of her shows? He said it meant so much to him! Maybe we replace "kill" with "spoon with, lovingly"?

PK: You're so much nicer than me, Anne! Given this is just a game and would by no means actually get Kevin Costner killed, he is easily my pick there. And then it gets tough. I mean, 1990 Antonio Banderas rivals 1960 Warren Beatty as one of the hottest versions of a person to ever exist on this planet, but even in 1990 Warren Beatty was still definitely giving sex god vibes. But I too am a person of little security, and he was about to meet Annette Bening anyway so I should not try and get in the way of that. So one glorious night with Warren, and a fiery marriage with Antonio where Pedro Almodovar would definitely officiate our wedding. 

ATD: I'll be there!

Queeries is Knegt's weekly column that queries LGBTQ art, culture and/or identity through a personal lens. Anne-iversaries is Donahue's bi-weekly column that explores and celebrates the pop culture that defined the '90s and 2000s and the way it affects us now. You can check out a few editions of both below.