Truth or Dare is one of the few documentaries whose legacy, it seems to me, continues to evolve. Madonna is still adding to her own legend, and Truth or Dare had such specific insight into her ambition, her sense of self, and even gay culture thanks to her dancers. How do you think the movie’s legacy continues to endure, especially in recent years?
Gosh, I’ll be honest with you. It’s not something I really think about. I kind of feel like that process is up to the individual. I’d say the most significant realization is when I meet people who say that the movie kept them alive in some way. It’s usually gay people, and they basically say it made them feel they weren’t alone in a time when they were vulnerable. That’s amazing to me, that that legacy lives on. We forgot that some of the stuff that we were making at the time was incredibly controversial for a mainstream film and a mainstream star. It’s that legacy that was the most significant for me, but I don’t know if that’s changed. I don’t even know if people watch the movie anymore.
It feels like this movie captures a hundred different storylines — about Madonna, her dancers, her crew and her family. Did you worry that wouldn’t cohere?
When I was shooting it, there was always that frustration: You’ve got a crew, you’ve got cameras, lights. It takes a certain amount of time to get to things. I probably missed 90% of the stuff, even if we shot 200+ hours of film. Then you realize that in the 10% you’re getting, hopefully there’s a way to show in a microcosm, two hours, the whole that you missed. That was my view while shooting. The thing about the documentary that made it so challenging is I tended to edit while I was shooting. Madonna tended up to bring up things, like her friend from high school. I would think, “Oh, we need to bring her in. We need to have her see Madonna.” There were points in the shooting where I thought, “We’re not getting enough of her vulnerability.” I have all this funny stuff and tough-person stuff, but I was missing a side of her that I knew by that point. A documentary is really about the relationship between the documentarian and the subject; that creates what you end up seeing. At that point, Madonna and I spoke every morning before she did anything and every night — just as friends catching up. There was a vulnerability to her, especially in the mornings. People didn’t get to see that, and that’s why I decided to shoot the mornings in her suite where she’s waking up and we hear all those voices talking about her. That was one of the few things that I shot where I didn’t place myself in the room. I knew if I placed myself in the room, she’d kind of be communicating to me. I was literally standing outside the suite and my film guys were in there. We got these beautiful images of her alone in this giant space, which to me was the metaphor. I think one of her people goes, “I think she’s this little girl lost in this huge storm.” Those are the kind of ways you try to create in a microcosm the fullest portrait of the person.