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Madonna Interview : Vanity Fair

“And at home, nobody brings up the fact that I’m a star,” she continues. “Not one word. At first I thought, Well, how come I’m not getting any special treatment? But even though I had to sleep on the floor in a sleeping bag, even though I didn’t know who else had slept in that sleeping bag, the trip was really such a joyous thing for my father.”

Madonna beams — she likes this memory. Family — whether natural, meaning her father and seven brothers and sisters (two are half-siblings), or extended, meaning the dancers on her tour and her assistant/agent/publicist/manager/lawyer team — is extremely important to her. In fact, her business associates are some of her closest friends. “People comment on it,” she says. “They say, ‘Do you realize all of your friends are on salary to you?’ And I say, ‘Oh, my, I really hadn’t thought of that, but maybe you could flip it around and think, Well, maybe I only work with people I really like.'”

And trust. A large part of the reason for Madonna’s success has been her faith in the people she works with. “She’s in control of that group,” says Jane Berliner. “She’s the matriarch of the family.”

Madonna structured it that way from the jump — her gilt has always been to make herself the center of the action. As a child growing up outside Detroit, she dreamed of being either an international superstar or a nun. “I would say I’m gonna be a nun’ like you would say I’m going to be famous.’ Then the nuns announced to me that a girl who wanted to be a nun was very modest and not interested in boys. After that, my role model was my ballet teacher, who was fabulous and demonstrative and extravagant. I wanted to be like him.

“I sometimes think I was born to live up to my name,” continues Madonna, who was named after her mother. “How could I be anything else but what I am having been named Madonna? I would either have ended up a nun or this.” When she left home at seventeen and moved to New York, she planned to be a professional dancer. “I sort of got tired of that after a while,” she says now, “because it was very difficult and there was no money in it.” She became interested in acting and was taking classes when she decided to become a singer. The rest is well documented: she started writing songs, she joined her then boyfriend’s band, she befriended a D.J., he became her boyfriend, she met this person, then another, and the pace started to pick up. From the moment she began performing, her goal was clear: Madonna wanted to conquer the world. And her clarity of vision was compelling.

“Madonna is more sophisticated than she was eight years ago,” says DeMann, her manager from the start, “but she has the same sensibilities as she had on the first day I met her. She had balls then and she has them now. I remember when she first walked into my office. I managed Michael Jackson then. She came in and I was absolutely smitten by her. She had three problems that day, three pressing problems, and I said, ‘I’ll make three calls and take care of your problems.’ And I did. The next day she called with five problems. The next day, she had eight The next day, ten. I said, ‘How can one person have all these problems?’ She said, ‘Well, I do.’ Madonna has that ability to grab you by the lapels and soon all you can think about is her.”

The rest of the “family” has a similar response – Madonna is not a passive star. She controls all aspects of her career, and she is integrally involved with every business decision, whether it be looking over a contract or choosing the plot and look of a video or deciding whether or not to endorse a product. “She’s a great businesswoman,” says Seymour Stein. “She’s very smart and she trusts her instincts, which are great. She also asks a million questions.”

And she’s stubborn. “I do what I want,” says Madonna. “I’m the boss. And, quite frankly, a lot of things I’ve wanted to do have met with adversity. I sort of cringe when I have to confront my manager, my publicist, whatever. I kind of think of them as parental figures. When I tried to explain my stage show to Freddy, I said, “I’m going to be on a bed and I’m going to have these two guys with bras on and…’ I could see he was just dying inside. I have to say, ‘I’m just going to do this and then you’ll see.’ But there’s always this preliminary shit that’s thrown and then there’s my shit fit and then I do what I have to do.” She smiles. “And then they like it.”

Madonna looks intent — she has very few doubts about her business acumen. She loves the game and she is almost completely immune to pressure from her advisers or anyone else. And they do pressure her — after all, there are massive sums of money at stake. Madonna reportedly pays DeMann 10 percent of her income, her business manager, Bert Paden, 5 percent, and her lawyers around 5 percent, each said to be capped at $1 million. When she is touring, a tour manager gets 10 percent of the concert revenues, and then there is Sire Records, a subsidiary of Time Warner, which has made an estimated half a billion on Madonna albums.

“There’s a lot of business stuff,” Madonna says. “But that didn’t come as a surprise. Besides, I love meetings with suits. I live for meetings with suits. I love them because I know they had a really boring week and I walk in there with my orange velvet leggings and drop popcorn in my cleavage and then fish it out and eat it I like that. I know I’m entertaining them and I know that they know. Obviously, the best meetings are with suits that are intelligent, because then things are operating on a whole other level.”

“What you have to understand with Madonna,” says DeMann, “is that she has substance. People forget that. Since she reinvents herself all the time and does these provocative things, people tend to concentrate on her image of the moment. But there is substance there. If you only resort to provocation. you don’t last long. Madonna is the biggest star in the universe. And she likes the view.”

Madonna - Vanity Fair / April 1991

It’s a Saturday night in early February and Madonna is sitting on a large dark-blue couch in the living room of her Manhattan apartment. She is discussing whether or not she would prefer to be male. “Fuck, yeah,” she says with great animation. “When I was a little girl. I was insanely jealous of my older brothers. They didn’t have curfews, they could pee standing up, they could take their shirts off in the summer, they got to do outdoor work, while we had to do the indoor work. They had so much more freedom and I would just mope about that. And mope and mope and mope about how I wished I was a boy. And then when I was in the ballet world I went through another period where I wished I was a boy because I just wanted somebody to ask me out on a date.” Madonna considers this notion for a moment. “Actually,” she continues, “it would be great to be both sexes. Effeminate men intrigue me more than anything in the world. I see them as my alter egos. I feel very drawn to them. I think like a guy, but I’m feminine. So I relate to feminine men.”