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Vanilla Ice reflects on the time ex-girlfriend Madonna proposed to him in the 1990s

Feb. 1, 2023
Vanilla Ice reflects on the time ex-girlfriend Madonna proposed to him in the 1990s

Vanilla Ice reminisced about the time Madonna proposed to him in the 1990s while appearing on the Just Jenny with Jenny Hutt podcast on Tuesday.

The American rapper, 55, dated the Queen of Pop, 64 — whose biopic was recently scrapped — for a brief time, and he recalled his surprise about her proposal.

'Things were going so crazy and fast, man. I was just like, "What?! I thought the guy was supposed to do that [propose]. 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!"' he said. 

'So, yeah. It was crazy. The more I think about it the more crazy it was,' the musician added.

The dynamic duo met in the early 90s when the Papa Don't Preach hitmaker attended one of his shows in New York City.

Vanilla Ice — born Robert Matthew Van Winkle — was in his early 20s at the time, while the Material Girl was in her early 30s.

And though he remembered seeing her 'dancing her a** off' in the crowd, the rapper added that it was 'intimidating' because of her star status.

'I remember she came back to the dressing room and said hello to me, and she kind of gave me the sexy eyes and I was like… ‘Well she's really too old for me, so I must be mistaken on that."'

However SBK Records co-founder Charles Koppelman, who's Jenny Hutt‘s father, informed the Texas native that Madonna was actually interested, and proceeded to set up the date between the two.

After the two began seeing each other the Ice Ice Baby hitmaker recalled things getting 'weird.' 

'It got weird. And I didn't know what was going on… My whole life is a snowglobe. You think Justin Bieber had it crazy? You have no idea what I had to go through, holy moly… My snowglobe was shaken up.'

And although he recalled the two had to wear disguises when they would go out in public, behind closed doors it was a 'normal relationship.'

'When you take away the [celebrity] factor… you have two people that have to deal with two people. It’s just basically her and I, and at that point, it wasn’t anything different than any other normal relationship.'

What broke the union apart was the release of Madonna's controversial table book, Sex in 1992, in which Vanilla Ice claims he was included without his permission.

'So, that book came out, and I thought it was so slutty. I didn’t want to be a part of it. I said, "How could you do that to me? And why did you do that to me?"'

'I could've sued her. I didn’t want to. I was like, "I don’t need that controversy. Let’s just let it go and you go your way and I go mine,"' he remembered. 

'And she called me all the time and she was not happy with it and upset and I’d have to hang up on her a few times, but that was it.'

Despite the not-so-friendly ending, the rapper admitted Madonna is 'a legend' and 'one of the greatest ever.' 

Last month Madonna attended the Miami Art Basel exhibition celebrating the 30th anniversary re-release of her Sex book.

Rive Droite re-issued 800 copies of her groundbreaking XXX tome - some of which will be signed and eventually auctioned off to benefit her Raising Malawi charity.

Back in 1992, Madonna earned the equivalent of $38.6M in today's dollars for the 132-page aluminum-covered book, which went on to sell 1.5M copies worldwide.

While controversial at the time, Sex is now well-regarded for its social and cultural impact and is considered a bold post-feminist, LGBT-beloved work.

Jean-Michel Basquiat (1982 - 1983)

Madonna briefly dated the late painter Jean-Michel Basquiat when both were rising stars in New York City. 

Sean Penn (1985 - 1989) 

The singer was famously married to actor Sean Penn, after the duo met on the set of her Material Girl music video. 

Their often tumultuous relationship came to an end in 1989, with reports citing Penn's unpredictable behavior as one of the major contributing causes.

John F. Kennedy Jr. (1997)

During a separation from Penn, Madonna reportedly dated the late John F. Kennedy Jr. for six months.

The romance with the political heir didn't last long, as his mother, Jackie Kennedy, was said to not approve of the controversial singer. Madonna also reportedly took issue with John's temper. 

Warren Beatty (1991) 

The singer dated movie star Warren Beatty after they co-starred in his comic book movie Dick Tracy, where she starred as singer Breathless Mahoney

The two ended up splitting due to their conflicting views of living in the public eye. 

Vanilla Ice (1992) 

Madonna dated Vanilla Ice for eight months before splitting in 1992. 

The Like A Virgin singer dated the Ice Ice Baby rapper when he was 23 and she was 32.

He reportedly broke up with the star after she published her infamous coffee table book called Sex, in which he was featured, saying he was 'hurt' to be part of it. 

Tupac Shakur (1994)

Madonna and the late rapper Tupac Shakur dated in the ’90s. The duo reportedly split up due to societal constraints.

Tupac told Madonna that he was uncomfortable with the image of dating a white woman because he 'would be letting down half of the people who made [him] what [he] thought [he] was' as he explained in a handwritten letter he wrote the pop star a year before he was fatally shot. 

Dennis Rodman (1994)

Following her romance with Tupac, the singer was briefly involved with former Chicago Bulls basketball star Dennis Rodman for two months.

Though only together for a short period of time, the athlete revealed Madonna wanted to have a child with him in his memoir, Bad As I Wanna Be.

Carlos Leon (1994 - 1997) 

Despite not being able to have a child with Rodman, Madonna went on to get pregnant with personal trainer Carlos Leon, whom she dated for three years. 

The two share a daughter, Lourdes Leon, 25, together and have maintained a good friendship.  

Guy Ritchie (2000 - 2008) 

One of Madonna's longest relationship is that with film director Guy Ritchie, whom she was married to for eight years.

The former couple reportedly met at the home of Trudie Styler (musician Sting‘s wife) in 1999 at a party.

They share son, Rocco, 22, and adopted son David Banda, 16, together. 

Jesus Luz (2008 - 2010) 

Shortly after her divorce was finalized, the star began dating 24-year-old Brazilian model Jesus Luz.

The former couple met at a W magazine photoshoot, but eventually split up due to not having many interests in common.

Brahim Zaibat (2010 - 2013)

Joining the list of younger models and dancers the star dated is Brahim Zaibat - a French dancer and choreographer - who was 24-years-old at the time.

He went on the MDNA world tour with her in 2012. The duo also showed up together to the 2013 Met Gala, where they made a fashionable pair in punk inspired outfits.

Ahlamalik Williams (2018 - 2022)

Madonna began dating her 28-year-old backup dancer, Ahlamalik Williams - who was almost 40 years her junior - in 2018. 

The pair called it quits after four years of dating in the spring of 2022. 

Andrew Darnell (2022 - present)

Madonna is currently rumored to be dating 23-year-old model Andrew Darnell.

The duo were first pictured kissing on the cover of Paper magazine in August, and were most recently spotted 'snuggling and cuddling' over Labor Day weekend at musician REMA’s concert in NYC.


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