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.
Did you ever just say to Madonna, “I feel like we’re not getting you vulnerable enough”?
Yeah! I told her that. I said that and she almost burst into tears! I said, “It’s not your fault! It’s just a tough thing to capture.” When she’s at work, she’s very professional, generally speaking. I think in the end I created as well-rounded a picture of the Madonna I knew.
A major triumph of this movie is how insightful its other interviewees are. How did you get, say, Madonna’s backup dancers to be so forthcoming with you?
One of the things I did was arrange to interview the dancers and get their background. As a documentarian, I had to discover the journey of these people. The only place I could be sure I could get them — since they wouldn’t show up otherwise — I would shoot them in bed in the morning. My crew would be there, they’d be half-asleep, and we’d ask questions. I think the fact that I was always around helped. When you’re shooting like that, people get lulled to a certain degree and they stop performing for the camera. And by the way, that’s what makes this different than reality TV. People say, “Oh, you invented reality TV!” I say, that’s totally different. Everything’s pre-planned. They plan a scene, then reshoot the scene to get all the different angles. None of that was possible for me. Madonna said to me, “You can ask me to do anything, but I won’t shoot something again.” The cameras ran for four months solid, and at that point people get familiar and drop their pretenses.
I’ve heard Truth or Dare referenced as a precursor to reality TV multiple times. Are there really no similarities in terms of narrative construction? Do you not watch any reality TV and think, “Oh, I innovated some of this”?
No, because I know how they do it. It’s a completely different technique. By virtue of the time I had, I know that documentary filming is mostly about patience. Reality programming is about, “We have a crew for three days. Can we make a perfect 22-minute episode?” That’s just not doable when you’re shooting a documentary. You want things to unfold. They need to know they have a story with a beginning, middle, and end for every episode. So I don’t really feel any technique is literally the same. But obviously the fascination with people’s behind-the-scenes life has become ubiquitous now. It’s just not the lives of singers and actors anymore because they have such curated lives. They want to control every frame of what comes out about them. They have Instagram and all sorts of venues to distribute their own supposed behind-the-scenes look, though again it’s fully curated. The difference with Truth or Dare different is that it was done at a time when it hadn’t been done before. And I don’t think it could be done now because too many people would get in the way.
Truth or Dare is filled with unforeseeable scandals, including the uproar Madonna’s controversial masturbation dance caused in Toronto. Was there any moment on the tour that seemed too huge to film? What was overwhelming about the experience?
Honestly, what was most overwhelming, initially, was that I convinced Madonna to let me make a movie based on interviews I did with her in bed. That flew in the face of all her advisors at the time. “She’s crazy. She couldn’t do this. It’ll never be successful. Why is she trusting a 24-year-old to do this?” So when she said yes, I would say that was the most overwhelming moment. I was like, “Holy shit. I’ve convinced her. Now what the fuck?” At that moment, you have no idea if you’ll have a real story! You need things to happen. But the more I shot, the more confident I got. At some point I realized I had an actual abundance of possibilities. That allowed me a great organizing principle for all of it.
The celebrity cameos in Truth or Dare remain unbelievable. Warren Beatty is the most famous one, but Kevin Costner, Antonio Banderas, and Sandra Bernhard drop by. Was the celebrity environment a circus?
You know, I actually didn’t have to deal with that. Madonna had big signs on her dressing room saying that anyone who walked in was agreeing to be filmed and be shown. There may have been a celebrity or two who tried to pipe in [on the filming process], but legally we’d covered ourselves. It’s not like the celebrities would come to me with that kind of concern.
I’m surprised more people don’t talk about the movie’s most shocking moment, when her makeup artist discussed being sexually assaulted on the tour. Howard Stern asked her about that moment on her show last year. What was that scene like, and what did Madonna think of it being in the movie?
I think there’s an idea that, obviously, I had pushed that answer out of her. But she was very OK with us filming. It certainly wasn’t like she came to us afterward and said, “Don’t include that part. That’s too much.” When something like that happens, you’re just shooting it. You’re just documenting it. The most I forced, in a sense, was the encounter Madonna had with her childhood friend. That I had prepared Madonna for. I said, “Look, I’m interviewing your friend who you spoke about. She’d love a chance to say hello to you. Would you do that for me backstage?” And she said, yeah, sure.
The live footage in this movie is some of Madonna’s most exhilarating live work. The climactic “Keep It Together” performance is my personal favorite. Do you have a favorite number?
You know, I like “Holiday” a lot. I think the performance captures two points of view. You see it from the audience but there are a lot of shots there specifically where you’re behind her. You’re almost experiencing that rush of being onstage with her. That was one of my hopes. I wanted to give them that vantage point. I thought that was exciting for them to see it that way.
Fans love how Truth Or Dare’s depiction of Madonna is both flattering and unflattering. How do you think the movie added to their perception of her?
Well, I think before this movie you had no idea about the depth of her intellect, wit, and control of her career. A lot of people dismissed her as that girl who crawls around onstage in a wedding dress, a created act. The movie showed a woman very much in control of her life and career. I mean, I have to say, she is still unbelievable in that regard. She is so astute. She is so smart. Working with her is a joy because you’re dealing with someone who is really professional and cares.
The way the movie incorporates the stories of Madonna’s dancers, most of them gay, is one of its richest features. Hell, you go to a gay pride parade. Did you plan on incorporating so much gay content ahead of time?
When I was shooting, I’ll be honest, we just shot every single day. That’s it! You know what I mean? So the dancers are going to the gay pride parade? So are we. In the edits, when you’re able to combine that editorially with certain points and themes you’ve built up, that has even more impact. Since 99% of what you shoot will end up on the cutting room floor, you don’t know what will stick. Due to neutrality, everything was filmed. But in the edit, it was an important aspect for me to show, I thought. Certainly it illuminated not just the dancers, but Madonna and her commitment to LGBT rights and AIDS even before it was remotely fashionable.
People might be surprised to learn you co-wrote Madonna’s 2011 directorial feature W.E. about Wallis Simpson and Edward VIII. That movie is not a documentary or even musical. How did you come to be involved with it?
I had directed a movie called Love and Other Disasters. I’d lived in London for ten years and tried to turn my back on Hollywood. It was based very much on my life in London, and because I lived in London, it showed I could write an English dialect. She thought I’d be helpful in the period aspects in the movie. Those were the elements that certainly most intrigued me. Because she knows me so well and my talents, she knew I was ultimately a writer. She asked me to do it and at first I resisted because I said, “This is your story.” But she said, “I need a collaborator, someone who can help.” It was a fun experience working with her again.
Finally, one of the more compelling aspects of Truth or Dare is how it depicts Madonna’s relationships, whether with close friends or notable acquaintances. Which relationship was most interesting to you?
Not to sound self-important, but I’d say the most important relationship I see when I watch that movie is the one she had with me. There’s so much generosity in what she ended up letting me shoot. That’s what got me. That’s what touched me the most. We were able to capture that.