VAN SANT: That’s a fantastic subject.
MADONNA: Their lives were absolutely crazy. It’s as much about the search for love and the meaning of happiness as it is about the cult of celebrity, really. It’s all kind of mixed up in one big stew.
VAN SANT: You wrote the script with Alek Keshishian?
MADONNA: Yeah. I started writing it on my own, and then I realized that I needed help. It’s just too big a subject. I quite like the idea of collaborating in general. Not only is it lonely to do things on your own creatively, it’s also kind of arrogant. I guess some people are brilliant enough to be brilliant on their own and never doubt anything and come up with fabulous things. But I think it’s good to get into arguments with people and have them say, “That sucks” or “You’re crazy” or “That’s cheesy” or “What do you think of this?” If anything, it helps you understand what you believe in and what you’re passionate about and what is shit. I think it’s important to have a sounding board. I’ve known Alek for years, and we have a weird kind of brother-sister relationship. One minute we’re hugging each other and crying on each other’s shoulders, and the next minute we’re slamming the door in each other’s face and not speaking to each other for a month. [laughs]
VAN SANT: When you’re writing together, is it a situation where you’re actually in the same room?
MADONNA: Oh, yeah. I mean, we’ll be in the same room, but we also do chunks of things on our own and e-mail them to each other, or we do stuff over the phone, or sit together and take the computer off each other’s laps, or we’re disgusted with how slow the other person is typing. . . . So it works in a lot of different ways.
VAN SANT: When you’re actually writing, do you have any kind of regimen where you write during the day or at night?
MADONNA: I tend to write during the day so I can see my children at night. But if my kids aren’t with me and I have a chunk of time when I’m a single woman living in my house for a miraculous week, I will get to write at different hours. I mean, we’ve burned the candle. We’ve stayed up all night. We’ve done it every which way. But generally we schedule chunks of time to be together and work on it.
VAN SANT: You’re just starting to fill out the cast?
MADONNA: Yeah, I’m casting. When I get back from Africa, I will officially begin preproduction.
VAN SANT: To shoot this summer?
MADONNA: Yeah. Yikes.
VAN SANT: I know. It’s hard, isn’t it?
MADONNA: Very hard. I don’t know what it’s like for you, but for me, making a movie, before you start filming and you’re in the trenches, it just seems like this process of pushing-of working through all of these people saying no. It seems like the whole world is against you. I’ve never had that experience before, because making records and putting my shows together-except at the very beginning of my career-I’ve never really experienced much resistance. I just find the people I want to work with and put it all together, and it’s a lot of hard work and all kinds of catastrophes happen, but I don’t really get too much resistance. But when you make a movie, it seems like there’s nothing but resistance. It’s kind of a miracle that any movie ever gets made. Every other day, it’s like, “What am I doing? This is insane. I could be off gardening right now. This is too stressful. Who do I think I am? Why am I putting myself through all of this punishment?” That’s what it feels like-for me, anyway.
VAN SANT: I’ve told people who have just started to make a film that the one thing you might experience is this feeling that everybody is conspiring against you, because you’re not necessarily able to tell what’s real and what’s not. There are all of these messages that you get through third parties that say, “You can’t get that location. You can’t shoot at Yankee Stadium.”
MADONNA: “That actor is not really available except for these three weeks.”
VAN SANT: Yeah. And it’s too hard for you personally to take care of it because there are too many things going on at the same time. It’s almost like torture.
MADONNA: It’s torture for me, because I want to personally go to all the people who are saying no to me and say, “Can’t we just work something out? Why can’t I shoot at your castle? Why can’t you make 30 outfits for me and not charge me? Why do you want to work with Martin Scorsese when you can work with me?” [both laugh] It all seems to be an exercise in acceptance, doesn’t it? When do you give in? When do you let go and stop trying to control everything? Filmmaking is such a collaboration. At a certain point, I suppose you do have to let go and trust the people you’re working with. I look at movies like Wong Kar-Wai’s films, and they all have such a familylike feeling about them. He just keeps working with the same actors and art director and DP, and the stories don’t change that much. There seems to be this familiarity there that must be such a nice luxury.
VAN SANT: Wong Kar-Wai is a really great inspiration. He’s always referred to as the Jimi Hendrix of filmmaking.
MADONNA: What does that mean?
VAN SANT: It means that he’s so loose and familiar with his craft that he can sort of do anything.
MADONNA: I was actually watching In the Mood for Love  again last night because I love the music. And I mean, how overused is slow motion in film? But, for some reason, he gets away with it. Every time the characters pass each other on the stairs, there’s that same piece of music. It’s so beautiful. He has these two married couples living next door to each other, and you never see the wife of one couple or the husband of the other, but you always hear them talking. And it’s not so much of a story, but you’re so sucked into it. It’s something to be envied. While the stories seem simple, you really end up feeling kind of devastated and moved and melancholic every time you watch one of his movies-well, I do, anyway.
VAN SANT: I do too.
MADONNA: But maybe there’s something wrong with me. Maybe I’m just a sucker.