Iconic celebrity couples from the 1990s – who is still together and who split up?


Vanilla Ice and Madonna had a whirlwind romance in the ’90s, but who knew the couple were almost engaged?

The 55-year-old rapper – real name Robert Matthew Van Winkle –made the revelation on the Just Jenny With Jenny Hutt podcast on February 1, saying he was shocked when the Material Girl proposed to him after just months of dating. 

“Things were going so crazy and fast, man,” the Ice Ice Baby singer recalled of their whirlwind relationship. “I was just like, ‘What?! I thought the guy was supposed to [get down on one knee].’ What do you mean? Wait a minute. This is too fast. I’m just getting started here, and I’m way too young for this!'”

“The more I think about it, the more crazy it was.”

The pair dated for eight months after they met backstage at one of his shows in New York in late 1991, with Madonna, now 64, aggressively sweet-talking the rapper. 

“She’s aggressive. She wanted me,” he previously said on an episode of the Dan Patrick Show. “She was much older, so I was like, ‘Whoa, what’s going on with this?’ She came into the dressing room right after the show. She grabbed me and we were having cocktails that night.” 

However, by 1992, Madonna’s infamous Sex book came out – and featured photos of the couple – Ice called it quits.

“It was disgusting and cheap. We were in a relationship yet it looked like she was screwing all these other people,” he told News of the World after the split.

“I thought she was taking pictures and running ’round naked because she was like that. Then when the book came out I was so embarrassed and ashamed. It was a porno.

“She threw me in like I was a product off a shelf and I didn’t appreciate it. That was it and I ended it. She said she didn’t have sex with these men but it looked like she was.”


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