This is the story of Madonna’s groundbreaking documentary 'Truth or Dare,' as told by those who made it happen
Photo: Gie Knaeps/Getty Images Truth or Dare is a snapshot of stardom in 1991, before fame was something that existed in people’s pockets. Pop documentaries have surged in the past decade, with many younger artists striving to make their own versions of Truth or Dare.
At the time, mystique was thought to be fame’s ultimate fertilizer, and Madonna’s then-boyfriend Warren Beatty scoffed that she “doesn’t want to live off camera.” Beatty wasn’t wrong, though: Madonna was an exhibitionist before everyone became exhibitionists. She came across as a freewheeling den mother and a haughty taskmaster rolled into one charismatic package, reflecting an age when celebrities weren’t yet required to seem “just like us.
Joanne Gair, Madonna’s makeup artist: Those eyelashes I made for the Blond Ambition tour book, which Herb Ritts shot, with little balls on the end of them — I made that by dipping broken eye shadow on the stove in a pot with melted wax. I put it on toothpick by toothpick. I would come with ideas: “Do you like these?” And that became such an iconic look.
“I Hope My Nana Doesn’t See This” Concert films, like Ladies and Gentlemen: The Rolling Stones and Talking Heads’ Stop Making Sense, were standard when Truth or Dare came out. Backstage documentaries, however, weren’t. Bob Dylan’s Dont Look Back — also captured in 16mm black-and-white — was a rare exception. Considering U2’s film Rattle and Hum saw a chilly reception in 1988, no one regarded Truth or Dare as a guaranteed home run.
Keshishian: In Japan, I started interviewing the dancers in bed. That was the only way I could make sure they showed up. They generally would wake up super late, go to the venue, do the show, and then they would be out all night. I was just curious about who these guys were. Who are these people who have suddenly landed in Madonna’s world?
Keshishian: While I was interviewing them, that’s when the cog started working in my brain. I was like, Wait a second. These are all amazing kids. They’re other. In some ways, they’re broken, they’re misfits in the world, and Madonna is playing their mother. That’s why, after Japan, I came back and was like, “Madonna, the movie isn’t what’s happening onstage. The movie is what’s happening offstage with you as the maternal figure to this group of Felliniesque characters.
Tim Clawson, producer: No disrespect to U2, but I think Alek captured something much deeper than what they put out. Rosenberg: It was Peter Pan and her lost boys, and although she talked about being maternal, she was also one of them. Oliver Crumes III, dancer: My dad told me if I don’t graduate he’ll disown me, but once he came and saw the show and realized what I was doing, he was okay with it. I’m grateful and thankful that it did bring us together. I’m glad that was in the movie so people can see what people go through. The tour taught me so much. On the set of “Vogue,” I saw two guys kiss for the first time. Before the tour started, I was homophobic. I wasn’t all with it.
Stea: Warren was so over us. He was like, “I’m at a different point in my life.” He was just rolling his eyes whenever we were invited along with her to places. I thought it was so sweet that she would take us everywhere. We went over to Warren’s house to celebrate his birthday. None of his friends were there, but yet there I am with some of the other dancers and Sandra Bernhard. I could tell on his face: “Well, this is what it’s come to.
Christopher Ciccone, Madonna’s brother, who served as the tour’s art director : My sister being my sister, she was acutely aware that being Warren’s girlfriend was wonderful for her mythology, her status in Hollywood. Keshishian: His lawyers were like, “Warren hasn’t agreed to be in this. He’d like to see the film.” And I remember Madonna going, “Tell him too bad because he saw all the signs that we were filming and he’s going to be in it and he doesn’t get to see it.”
Putting Harvey Weinstein in His Place After 200 hours of behind-the-scenes footage and 50 hours of concert footage got culled down, Miramax acquired the domestic theatrical rights. Harvey and Bob Weinstein’s company was still on the rise, having recently released Sex, Lies, and Videotape, The Grifters, and Paris Is Burning. Harvey wasn’t yet a top-line power broker, giving Madonna the upper hand.
Rosenberg: I think he was a little afraid of her, since he’s into having power over women. He understood he was not in a position to give her shit. Keshishian: I would read some of those articles [about the tour and documentary], and it made it seem like she was this marketing genius who would sit at the table rubbing her hands going, “What’s my new persona going to be?” It wasn’t that. It was so instinctive and natural to her. I always likened it to, “Imagine a 12-year-old who runs into the attic and picks up a new outfit.”
Brown: One of the things that knocked me out is that party they do in France. She’s staying in this great hotel where she has a party for everybody at the end of the tour. Finally she kicks everybody out to go to bed, and she goes around her suite and cleans up. That was one of the last things shot, and I thought, That’s the beginning of the movie. Whatever you might think you know about Madonna, you probably don’t know her at all.
Crumes: I looked at it like I had to protect myself. I didn’t have a contract for [the film]. There are a lot of die-hard Madonna fans that are mad about the fact that we didn’t get paid. It was so much of a vulnerable movie, and it showed every weakness and strength of everyone. Gabriel’s family didn’t know he was gay. We should have all gotten paid because it’s still making money.
Crumes: It’s water under the bridge for me. No matter what, I’m always going to still love her. Elvis, to me, don’t have nothing on Madonna and Michael Jackson. Sorry! Lady Gaga and Beyoncé don’t have nothing on Madonna and Michael Jackson. Nobody will ever be better than both of them. I have nothing but love for her, and I wish one day I’ll get to see her again.
Brown: Spike Lee said to me, “What, you’re gonna go out and do a Madonna film?” I said, “Yeah, I am. You’ve written Madonna off and you’re wrong about her.” He said, “Yeah, yeah, maybe.” And then next I hear, they’re meeting up in Chicago. Oh, you put her down, but now she’s your girl, right? Later, Spike said, “Yeah, Madonna’s cool, she’s all right.”
Roewe: In a sense, Madonna was showing herself to be vulnerable and to be made fun of. That’s one of the things that gave it credibility. It felt real. It wasn’t, “I’m going to tell you the Madonna story.” It was, “You’re going to see the rough sides of me and see me without makeup,” which at that time was not done.