Vanilla Ice Dishes on Dating Madonna: “She Made Me Look Like the Biggest Fool on the Planet”

LOS ANGELES, CA – Vanilla Ice, the rapper who took the world by storm with his 1990 hit “Ice Ice Baby,” recently opened up about his whirlwind romance with the pop icon Madonna. During an interview with DJ Vlad, the 56-year-old rapper reminisced about the brief but memorable time he spent dating the “Material Girl” singer in the early ’90s. Here’s a deep dive into the steamy details and the dramatic fallout that ensued.

vanilla ice madonna

The Night It All Began

Flashback to 1991, New York City was buzzing with excitement as Vanilla Ice performed at Madison Square Garden, one of the most iconic venues in the world. But little did he know, his life was about to take a wild turn. As the lights dimmed and the crowd roared, a surprise guest made her way into the venue – none other than Madonna herself. According to a 1991 Los Angeles Times report, they actually met at the smaller, more intimate Beacon Theatre. Yet, regardless of the venue, the encounter was unforgettable.

Madonna, who was at the height of her fame with hits like “Vogue” and “Like a Prayer,” had just completed her blockbuster Blond Ambition Tour the previous year. At 32, she was a global superstar, and the fact that she chose to attend Vanilla Ice’s concert only added to the night’s allure.

In his interview, Vanilla Ice, born Robert Matthew Van Winkle, recounted the moment Madonna arrived backstage. “She came in [to the dressing room] and said ‘Hello,’” he recalls. “She was dancing the entire time, and she was right there in the front row, just a little bit to the left with her crew and her entourage. They were all dancing, heavy dancing, like sweating. I was looking at them like ‘Damn, Madonna’s dancing more than everybody in the crowd.’ And these are all teenagers.”

A “Normal” Celebrity Romance

After the show, Madonna and Vanilla Ice exchanged numbers, kicking off a romance that he describes as surprisingly “normal.” Despite their high-profile status, they managed to keep things low-key. Vanilla Ice described her as a “sweetheart” and a “legend,” though he remained tight-lipped about the intimate details out of respect for his current wife.

However, as the saying goes, all good things must come to an end. For Vanilla Ice and Madonna, the romance took a nosedive with the release of Madonna’s controversial 1992 coffee table book, Sex.

The Controversial Sex Book

Madonna’s Sex book was a boundary-pushing project released alongside her Erotica album. Filled with provocative and explicit photos, the book featured various celebrities, including rapper Big Daddy Kane, supermodel Naomi Campbell, and Vanilla Ice himself. The images shocked the world and caused a media frenzy, but for Vanilla Ice, it was a personal and professional betrayal.

“I didn’t know they were gonna do a sex book and have me in there, you know?” Vanilla Ice said, still visibly agitated by the memory. He labeled the book a “slutty package” and claimed he never gave permission for his inclusion. “She made me look like the biggest fool on the planet. So that was the end of it for us.”

When DJ Vlad pointed out that Vanilla Ice must have noticed the photographers, the rapper acknowledged the constant presence of cameras but maintained that he was blindsided by the book’s release. “When it came out, it was shocking and it ended our relationship. But who gives a shit, man? I’m happy. I got kids, [a] beautiful wife and, you know, love is real.”

Madonna’s Marriage Proposal

In a twist straight out of a Hollywood romance, Madonna even proposed to Vanilla Ice during their brief relationship. “Who proposes to a guy?” he mused. “I told her I’m way too young for you … The oldest girl I’ve ever dated in my whole life.” This revelation added another layer of intrigue to their relationship, which has since become a curious footnote in pop culture history.

Vanilla Ice isn’t the only one to claim Madonna’s unconventional proposals. NBA legend Dennis Rodman also revealed in a 2019 interview with The Breakfast Club that Madonna allegedly offered him $20 million to get her pregnant. The Queen of Pop certainly has her own ways of making headlines.

Moving On

Reflecting on his past with Madonna, Vanilla Ice dismisses their relationship as a fleeting chapter in the saga of his life. He hasn’t seen or heard from Madonna since the debacle with the Sex book. “If she called me on the phone, I wouldn’t answer it. Never,” he asserted.

Post-Madonna, Vanilla Ice’s personal life took a more traditional turn. He married Laura Giaritta in 1997, with whom he shares two daughters, Dusti Rain, 26, and KeeLee Breeze, 24. Though their marriage ended in a protracted divorce finalized in 2019, Vanilla Ice found love again. He welcomed another child in 2018, proudly sharing the news on his Twitter account.



Vanilla Ice’s brief romance with Madonna remains a tantalizing tale of celebrity passion and drama. From the electric energy of their first encounter to the shocking fallout over the Sex book, their story is a vivid reminder of the unpredictable nature of fame and relationships in the spotlight. As Vanilla Ice looks back on those days, he seems content with where life has taken him – away from the limelight’s chaos and into the steady rhythm of family and real love.


Exit mobile version