The Picture | The Story

It has always been my goal to surprise an audience with an image that challenges preconceived notions of a particular subject, especially if that person is extremely well known.

I like to think of my photographs from the 1980s as attempting to be entertainment experiences all on their own. And I often leave small clues behind in my images that might amuse my audience with a sly touch of wit.

For this portrait of Madonna, it’s important to remember the context of the period in which it was made, the late 1980s. At that time, Madonna was widely known as the “Queen of Reinvention,” because for almost every new song, album cover, video, etc, she presented herself in a completely new or different way.

Another element to consider is that the 1980s saw the beginnings of a shift in traditional gender presentation – particularly in the pop music world – and we are still living with the results of that shift in the pop culture of today.

I decided to dress Madonna as a man. And that of course led me to think of the ways in which Hollywood glamour star Marlene Dietrich presented herself, particularly in the 1930 film Morocco directed by Josef von Sternberg.

So, I studied that film, and I discovered a scene in which Dietrich sits before a makeup mirror on which is inscribed (in lipstick), “I changed my mind Good luck.” This struck me as potentially amusing in the context of Madonna and her many reinventions, so I decided to base the concept of my portrait on that moment in the film.

By including that loaded phrase on the mirror in my image, it was as if she was saying to her audience, “Good luck trying to understand me. You thought you knew me? Not so much.”

A few more things to point out in this image: It’s not really backstage anywhere, it’s a set of backstage, one that I had built in my studio. On the back of one of the scenery flats is a sign that says, “No Smoking.” But of course, rule-breaker Madonna is flaunting a lit cigarette. One of the songs that made Madonna’s career was called “Lucky Star,” and if you look very closely at the image, you can see clearly that the cigarette is labeled, “Lucky Strike.” And of course, the words “Good luck” in the mirror inscription also refer to Lucky Star.

Another interesting note, Madonna had never yet presented herself cross-dressed, nor had been made to look like Marlene Dietrich, nor had any image of Madonna ever referenced the post-Weimar aesthetic that von Sternberg and Dietrich brought to Hollywood in the 1930s.

Clearly, this image had its own effect on Madonna personally, because four years later, she presented herself almost exactly in the style of this image for her video “Vogue,” directed by David Fincher.

• Matthew Rolston, 2018