Standing in front of 140,000 fans at London’s Wembley Stadium, performing with the woman who is arguably among the most iconic and successful pop stars of the 20th century, should have been a pinnacle of Carlton Wilborn’s professional life. He was one of Madonna’s lead dancers for The Girlie Show and Blond Ambition, two of her biggest concert tours, and two of the biggest tours overall of the 1990s. Rolling Stone called Blond Ambition a “sexually provocative extravaganza” and “the best tour of 1990.”
Blond Ambition wasn’t just a tour, though. It was a spectacle that, after it was filmed, became the most watched TV special to date for HBO (with 4.3 million households viewing), and it spawned the 1991 documentary Truth or Dare, which became not just a mainstream success (it grossed $29 million, making it one of the highest-grossing documentaries ever) but a bona fide gay hit. Two of her male dancers kiss, the troupe attends an LGBT pride parade, and Madonna pays tribute to her friend Keith Haring, who had died of AIDS complications in 1990. It is a very gay film that was as huge culturally as the concert series. And Wilborn was there in the midst of it all, in the film, performing onstage.
Carlton and Madonna on stage (below)
He had it all, but there was something off. Something not quite right. Perhaps because he was keeping a secret. “I’d get these grand opportunities—and now I’m touring the world and now I’m at Wembley Stadium with Madonna and we’re doing these grand things—and I had this huge secret that nobody knew about,” he recalls. “I don’t feel it so much now, but there was a somewhat recent feeling of sadness about that time for me in reflection, in that, man I was really not able to ever sit in the glory that my life was having because there was this on-the-down-low truth going on that was [stopping me from] feeling amazing and being really excited about what I had.”
One of the highlights of Wilborn’s professional experiences came during the Girlie Show tour. “Madonna created an eight-minute number that was exclusively a highlighted moment for me,” he says. “She was not on the stage. It was a piece that was set completely around me. I was the leader of the thing, and I had eight minutes to entertain 120,000 people.” But like all moments during those years—after Wilborn discovered he’s HIV-positive but before he told anyone—it was tempered. “Because as excited as I was, it’s 10:30 at night and the sound is booming and the audience is screaming for us, and I’m also aware that it’s 10:30 at night and we’re in a city or a country where it’s cool outside and all I have on is briefs, and God forbid I should be cold or get a chill. I’m fucked.”