The pop icon on election-night prayers, aging, and bad wine.

Madonna has no patience for bad wine. I learned this while sitting in a well-appointed living room at her New York City home, with Nina Simone playing softly in the background. I must tell you, Madonna’s house smells amazing—something delicious, maybe roasted chicken, was cooking in a kitchen elsewhere in the manse, and there was a gentle fragrance in the air, jasmine, perhaps. While I waited for Madonna, her day-to-day manager, her publicist, and I chatted while reclining on gorgeous cream-colored furniture set upon the largest rug I’d ever seen, on top of immaculate black wood floors. On the wall behind me was a black-and-white photograph of a woman perched on the edge of a mussed bed, scantily clad, sucking on a gun, it’s Helmut Newton’s “Girl with Gun” photograph. Of course.

 

Gucci cape, hair band, and shoes; La Perla bodice; Erickson Beamon earring; H. Crowne body chain; Mordekai by Ken Borochov rings; I.D. Sarrieri suspender belt; Maison Close stockings.

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Madonna was late, but that didn’t matter because she is Madonna. What is time, really? She was all apologies when she arrived, and we quickly got down to business. She was in the process of planning a fund-raiser at Art Basel in Miami Beach, and like any perfectionist she wanted to taste the wines that could be served. She knelt on the floor as she considered various reds and whites and a rosé—or “summer water,” as she called it. “Roxane,” Madonna said. “You don’t have to wear that dress tonight. …” That’s when I exhaled. This was familiar territory. My name is part of a well-known song or two. I smiled and said, “No, I do not.” At one point she asked me for my opinion on a particularly troublesome wine, handed me her glass, and swore she didn’t have anything contagious. I believed her and took a sip. To be fair, the wine was terrible—it tasted like vinegar—and the year on the bottle said 2016, so it wasn’t really wine yet. It was the suggestion of wine.

Madonna is very good at multitasking. While she was considering the wines, she held forth with me, and before long she was done with the bad wine. “Take the mediocre out of here,” she tells Dustin, the strapping young man who served all the wine and apologized for its mediocrity even though that mediocrity was not his fault. “I’ll go broke before I drink bad wine,” she declared, and I was entirely in agreement. I wanted nothing more than for Madonna to offer her opinions on wine for the rest of the evening. Dustin promptly brought us the good wine, served in a crystal decanter. I drank it, and it was, indeed, good.

Christian Dior c/o the Way We Wore vintage jacket; Stella McCartney bra; Agent Provocateur waist cincher; La Perla briefs; Wolford stockings; Lynn Ban custom rosary body chain; Madonna’s own garter belt.

In the days leading up to our conversation, I kept wondering what I could possibly ask Madonna that she hadn’t already been asked. She has been a figure in popular culture for more than 30 years. There was plenty I was curious about. I mean, I grew up on her music. As a good Catholic girl, I was obsessed with “Like a Prayer” and how she blended transubstantiation and eroticism. I listened to The Immaculate Collection nonstop. I coveted her book Sex, which came out just as I turned 18. I’ve been intrigued by her personal life. I’ve admired her stamina and artistic evolution. But I didn’t want to ask silly questions. I didn’t want to pry even though my job was, of course, to pry.

 

“I don’t believe there’s a certain age where you can’t say and feel and be who you want to be.”

 

 

Over the course of an hour, we talked about a great many things, but we started with her upcoming movie project, Loved, an adaptation of Andrew Sean Greer’s novel The Impossible Lives of Greta Wells. On her coffee table, there were binders filled with research for the project—potential settings, costumes, and so on. Madonna is thorough. In fact, she co-wrote the screenplay and will be directing the film. The novel follows the title character as she moves through time and negotiates three different lives she could have lived. The story also focuses on Greta’s relationship with her gay twin brother, Felix, in those different lives. “It touches on a lot of really important topics I’ve always been invested in or championed—fighting for women’s rights, gay rights, civil rights, always fighting for the underdog,” Madonna says. “I’ve always felt oppressed. I know a lot of people would go, ‘Oh, that’s ridiculous for you to say that. You’re a successful white, wealthy pop star,’ but I’ve had the shit kicked out of me for my entire career, and a large part of that is because I’m female and also because I refuse to live a conventional life. I’ve created a very unconventional family. I have lovers who are three decades younger than me. This makes people very uncomfortable. I feel like everything I do makes people feel really uncomfortable. Why does this book appeal to me? Why did I want to adapt it into a screenplay? Because it touches me on so many levels and it deals with so many important topics. Right now, more than ever, it’s an extremely timely story to tell.”