In the early days of September 2001, I was driving down Santa Monica Boulevard on my way to a call-back for Guy Ritchie’s adaptation of Swept Away, starring his then-wife Madonna, when it dawned on me: Instead of turning left toward the office buildings, I would be veering into the residential area. I was going to Madonna’s house. Her music had been the soundtrack to my preteen angst, and she was my idol as a feminist and as an artist. Naturally, I pulled the car over, called my sister and had a mini-freak-out.
When Madonna walked into Guy’s home office that day, her little son, Rocco, was perched on her hip. She told me that my audition was funny and that I’d be good in the movie, and I just tried to keep breathing. I assume it was in that moment that Guy concluded I’d be the perfect, nubile idiot to cast in Swept Away. I won the part. The next few weeks were surreal for all of us. I had seen Madonna in concert as a teenager and had splurged on tickets for her Staples Center show scheduled for Sept. 11, 2001. Needless to say, that concert was postponed as the world came undone. But a couple of weeks after we met, I watched Madonna finish her Drowned World Tour. Before the music began that night, she started with a prayer for peace: “If you want to change the world, change yourself,” she told the crowd. Through tears, I sang along for the entire show.
Anyone who has ever had the opportunity to work alongside her — as I did in Malta during those next couple of months — understands why Madonna is Madonna. She works harder than anyone I’ve ever met; she exists in this world by her own rules; she has remained in control of her own voice, paving the way for the Taylor Swifts and Adeles of the world to do their thing in the process. During the course of her more than three-decades-long career, all of those instincts have helped her land the most top 10 singles on the Billboard Hot 100 chart, and hold the record for the most No. 1s by any act on a single Billboard list (46 No. 1s on Dance Club Songs). With more than $1.3 billion earned from her groundbreaking concert tours through the years, as reported to Billboard Boxscore, she now reigns, at age 58, as the highest-grossing female touring artist of all time. Her most recent trek, the Rebel Heart Tour, grossed $170 million during the course of 82 performances, concluding in March 2016. (A concert film chronicling the tour, Madonna: Rebel Heart Tour, premieres Dec. 9 on Showtime.)
On a recent Monday afternoon in between parent/teacher conferences for my kids and meetings for Pitch Perfect 3 — a film that focuses on young women finding harmony through music — Madonna and I reconnected over the phone. Since there is no shortage of Madonna books, articles, blog posts and career analyses, I just wanted a snapshot of Madonna right now, in this moment, because she is a woman who lives in the present and never looks back.
Where are you today?
I’m in New York, trying to get my Raising Malawi art auction together for Art Basel in Miami. Just dealing with artists and temperamental people.
How many artists will you feature?
It will probably be 12 amazing works of art. I wanted to keep it to artists that I collect myself or I’m friends with or art from my own collection. Originally it was just going to be art, but now it’s also experiences, so I’m trying to make them as interesting as possible. For instance, one is a trip with me to Malawi, where my son and daughter [David Banda and Mercy James] are adopted from. Another is playing poker with Jonah Hill and Ed Norton, and another is staying at Leonardo DiCaprio’s house in Palm Springs for a week. I didn’t think it was going to be as complicated as it is, but, oh well, that’s life. It’s complicated because I’m involved with everything: the lighting, the curtains, the flowers, the decor, the food. I’ve tasted too many bad bottles of wine. This auction is an extension of me, so I want everything to be beautiful, tasteful and well-appointed. It becomes exhausting because I need to be involved in every aspect of it: the people who are speaking, the clothes people are wearing, the music on the playlist.
Will there ever be a time that you let go of that control, or is this like, “I have to?”
I have to.
Where does that come from?
Obviously, you could say it has to do with my childhood, if you’re going to psychoanalyze me: My mother dying and me not being told, and a sense of loss and betrayal and surprise. Then feeling out of control for the majority of my childhood, and becoming an artist and saying that I will control everything. No one will speak for me, no one will make decisions for me. You could say I’m a super control freak. That’s what everybody likes to say. I don’t want to have an event that I’m not proud of. It’s like everything that I do. My shows, my films, my house, the way I raise my children. I take great offense when details are overlooked.