When Madonna and Vanilla Ice Used Funny Disguises to Avoid Being Recognized Together

Madonna has a history of odd pop cultural couplings, including her relationship with the King of Pop, Michael Jackson. She once dated Robert Van Winkle, also known as Vanilla Ice. At the peak of their careers, Madonna and Vanilla Ice spent a good eight months dating in the early 1990s.

Vanilla once came on Jenny Hutt's Just Jenny podcast, where he revealed that the two first met at one of his sold-out performances in New York City. The relationship came to an end several months later with the release of Madonna's explicit photo book, Sex, in the autumn of 1992, per The Grunge. "She put me in that book without my consent, without my knowledge, without anything. ... That book came out and I thought it was so slutty, I didn't want to be a part of it," Vanilla told Hutt.

But while the two were dating, they were at the top of their careers and couldn't risk being papped together. In an interview with Canadian television personality George Stroumboulopoulos, Vanilla opened up about their strategies to avoid being seen together.

He shared, per Jezebel, "Like, we would go to movies. We had disguises. I had a mustache and a hat with hair coming down, and she would go as an old lady. And we would walk in and the bodyguards would [be] like 20 feet behind. Ya know, kinda lookin’ just like we’re nobody. And just walk in and go and see our movie and just have a good, normal... we’d do dinner that way and nobody would ever recognize us. It was the greatest."

Even though Vanilla's musical tastes might not age well, he will always have the anecdotes of his Florida real estate flipping firm and his dress-up sessions with Madonna. It's not the world's worst legacy. In 1994, he talked about the highs and lows of their relationship in an interview, per NBC Washington. “She would call me at strange hours, ‘Are you in bed with another girl?’ At 6 in the morning, man, I’m like, ‘I’m [expletive] sleeping all alone. What the [expletive]? Why do you keep doing this?’” he recounted. “But is she a sexual animal? Nah, she’s like every normal girl, man. She’s very sexy, she’s hot, she’s romantic. She’s got a great body for her age [35].”

Aside from the Sex book debacle, Vanilla was also not at the same stage of the relationship that Madonna was in. The Queen of Pop and he broke up, according to Vanilla, partly because she wanted to commit to him more than she did to her former partner Sean Penn. "I was digging her," he said in Andrew Morton's book Madonna, per PEOPLE. "But there was a desperate neediness about her, an impatience to get married." He added of Madonna's torch for Penn, "I felt that she still loved him. In fact, I know she did because she told me."