I was 26 and living in Los Angeles when Madonna had a huge open-call audition for the Blond Ambition tour – there were maybe a thousand men there. By the time I got home I had a message: “Come meet me at the club tonight.” It was basically a callback, like, let’s see who these people really are, how they hang with alcohol. She herself being an alpha type, she was looking for very confident people – the best of the best – so I was acutely aware of how I was presenting myself. When I made the cut, I knew it was a huge opportunity.
Touring was different back in the 90s. We really got to do it in the rock’n’roll way people imagine – private jets, two separate chefs, a bowl in the studio lobby stacked with cigarettes. It’s very rare that dancers are given that kind of treatment. And the afterparties – oh my gosh, are you kidding me? We won’t say much about those!
Every single night, the blast-off energy from the crowd was crazy – they were so loud we could hardly hear the music. We had done so much training at this point – the rehearsal process was truly like boot camp – and it was great to finally be in the sweat of it all. When I heard her singing to an audience for the first time: it was like: “Oh shit, she’s fucking performing now.” And it was a lot of fun working with an artist who had started in dance and who could do all these intricate moves with you.
Madonna was great to work with. I was having this conversation with someone the other day – they were saying, “I bet it was crazy, when she was being really intense in the rehearsals, making people feel bad.” But that’s not what she does, at all. She has [one] personality that she knows makes her money – a bit brash and snappy and in your face – and then she has who she [really] is: just a chill, regular person. It was also a special time because she was single, didn’t have any children, and hadn’t really come against any extreme pushback, so she was very free. It was great to be a part of that.
She started as a street artist in lots of ways – a Lower East Side New Yorker kind of chick – and she likes to pull from where she came from.
When I was booked, I had nothing to do with voguing: I was classically trained – the underground art world was not my thing. At the time, voguing was very exclusive to that [New York black and Latino LGBT] community. Now you have all kinds of people voguing and I think that’s a great thing.
She was able to dive into something that had a strong pulse and felt it was important to get the word out to the consciousness of young gay dancers – it was about helping these people thrive and feel good and powerful.
What’s really great about her as a performer is that she is there to sell a story, however far she has to go. There are artists now who are taking the baton – Lady Gaga is probably the closest to it. But Madonna continues to be special because she’s just balls-out as an artist. At the core of what she represents is the secret longing of every human being: we all have quiet thoughts, we all have hungry thoughts, but most of us have been conditioned to think it’s inappropriate to let this be known. So when you have an example of somebody who is living their life against all the constructs that are blasted through the world and the media, it’s intoxicating.
Madonna has always been a very generous person. There was a particular time in my life [in 1995, when Wilborn was going through a difficult time, Madonna let him live with her for several months] where she really showed me the human side of her – I’m not saying that’s the first time she showed this to me, but it was the degree of it. It was really amazing when she offered me that. After that our paths went in different directions. I auditioned for the Drowned World tour and didn’t get chosen. I started going after different things, she was doing different things. Life happened. What I would say to her now is: happy 60th birthday! And thank you. Thank you for allowing me to let all of my power be seen and expressed
• Matt Cain on Madonna: ‘She opened up gay culture to the mainstream’
