Here's What Really Ended Madonna And Vanilla Ice's Relationship

Queen of Pop Madonna has made a name for herself writing dancey pop tunes that almost always deal with love, romance, sex, and all the fun (and disasters) therein. Perhaps art imitates life, as Madonna has dated plenty of fellow stars. There were her two marriages to film giants Sean Penn and Guy Ritchie, and she famously dated Warren Beatty, basketballer Dennis Rodman, and rapper Tupac Shakur. And to this day, her love affairs still make headlines, as evidenced by her breakup with backup dancer Ahlamalik Williams after three years. Madonna then sparked more romance rumors after being spotted getting close with model Andrew Darnell. The notable age gap in her relationships prompted her to comment to Harper's Bazaar in 2017, "I have lovers who are three decades younger than me. This makes people very uncomfortable. I feel like everything I do makes people feel really uncomfortable."

One of Madonna's first public romances where the age gap made waves was way back in the early '90s when she had a brief but notable affair with "Ice Ice Baby" rapper Vanilla Ice, per InStyle. Yes, the man who wanted us all to "stop, collaborate, and listen" was once the beau du jour of the Material Girl. For 30 years, the one-hit wonder and "Dancing On Ice" contestant has made their short-lived fling a talking point in almost all of his press interviews. And often, he includes some wild claims about why their tryst didn't last. 

Back in 1991, "Vogue" songstress Madonna was the most famous pop star in the world, and her provocative tour documentary, "Madonna: Truth or Dare," was about to change the face of rockumentaries forever. At the premiere, none other than rapper and pantsuit aficionado Vanilla Ice made an appearance on the red carpet. Although Madge and the rapper weren't seen together at the event, they later did a flirty and funny skit together when the "La Isla Bonita" singer accepted a Smash Hits award. It seems they were off to the races after that. 

According to Vanilla Ice, they had a gas trying to go out on movie dates unrecognized. On "George Stroumboulopoulos Tonight," he recalled, "I had a mustache and hat with hair coming down, and she would go as an old lady." He also called their fling a "normal relationship." But if there was a problem (yo!), he solved it by breaking up with Madonna when compromising photos of the two appeared in her notorious 1992 "Sex" book. 

"I was hurt to be an unwitting part of this slutty package," he told News of the World (via Digital Spy). "It was disgusting and cheap ... 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." His slut-shaming comments may have been fair game in the '90s, but these days he's singing a different tune.

After Madonna and Vanilla Ice called it quits, the rapper would harp on their age difference, telling News of the World (via Digital Spy), "She was older than me and a great lover. She's still the oldest person I've ever been with, so it was an experience." Later he told USA Today in 1994, "She's got a great body for her age" (via Access). If you're thinking those comments haven't aged well, luckily the "Cool as Ice" star has changed his tune. He told George Stroumboulopoulos during an appearance on the host's eponymous show that the "Ray of Light" singer was actually "a sweetheart." 

When confronted in 2011 by paparazzi for comment on Elton John's beef with Madonna over her beating him in the best original song category at the Golden Globes, the "Ice Ice Baby" rapper actually came to her defense, insisting that she deserved to win.  

Madonna, on the other hand, has made a point of poking fun at Vanilla Ice. Speaking with Us Weekly in 2015, the pop icon quipped, "If I were trapped on a desert island with either [ex-boyfriend] Vanilla Ice or Dennis Rodman, I would pick Dennis. He has a better sense of humor. Plus, he could always wear my clothes."