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Madonna & her new movie star Andrea Riseborough

On the release of her film, W.E., the superstar talks women, power and sexuality. Read the interview below, plus see her fashion shoot with actress Andrea Riseborough, and Madonna's most iconic looks.

Madonna lives behind high, spike-topped, black metal walls in three townhouses joined into one on New York's Upper East Side. I had to manage my covetous feelings as I was ushered through the gate and then walked through pristine living rooms, dining rooms, and sitting areas, all decorated like the highest end of British hotels, in a mélange of blacks and grays. There were glossy black floors and doors, original Tamara de Lempicka paintings on the walls, and, I would swear, a wall covering made of teal duck feathers in at least one bathroom. But I was open to forgiving Madonna all of these signs of her success because the fact is, I think the woman is gutsy, and the risks she has taken in her career have made the world a bit freer and more interesting for women of my generation.

In person, Madonna is tiny and alarmingly fit, and she has the posture of a seasoned dancer. Her face is more delicate than in photos; one gets the sense that she is aware of her every gesture. She is wearing beige slacks with boots and a belted beige sweater over a white shirt; her hair is simply styled in blonde waves. She greets me warily and welcomes me into a quiet study.

Then the surprises begin. Throughout my formative years, when she was so iconic, I had always assumed that Madonna had been brave in her choices because of some innate egotism or some aberrant strength of will. In person, I discover that she has been brave in her life in spite of lacking certain kinds of protection, privilege, and confidence. What I hadn't expected to feel was moved. At 53 years old, I find, Madonna is scrappy, really smart, and young in the way that people who have had a childhood trauma — she lost her mother when she was five years old — often seem to be. She is very guarded at times and then, as we speak, more open, even vulnerable.

"For some reason, I feel like I never left high school, because I still feel that if you don't fit in, you're going to get your ass kicked," she says. "That hasn't really changed for me. I've always been acutely aware of differences and the way you are supposed to act if you want to be popular."

I have always been intrigued with Madonna as a provocatrix, and her latest venture is no exception to that record. Her new directorial project is W.E., a cinematic version of the story of Wallis Simpson, the American divorcée for whom British monarch King Edward VIII famously abdicated the throne in 1936. It premiered at the Venice Film Festival this fall to mixed reactions and will open stateside in December. "Making movies is really hard. It's the hardest thing I've ever done," she says.

The film, which Madonna also cowrote, juxtaposes Wally (Abbie Cornish), a modern-day trophy wife who has everything on paper but is trapped in an abusive relationship, with a mythical version of Wallis Simpson, played by Andrea Riseborough. The two women's stories intertwine when Wallis enters the mind of the later Wally and serves as a kind of muse and mentor to her, attempting to spur the young woman from depressed passivity to agency in her own situation. "Get a life," Wallis says sharply to Wally in one of my favorite scenes.

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