What Ever Happened to Vanilla Ice After His One Hit?

Vanilla Ice is a one-hit-wonder who gained incredible fame with his smash hit “Ice Ice Baby.” He was welcomed into the world as Robert Matthew Van Winkle (no, his birth name is not Vanilla Ice). As the product of a broken home, Vanilla Ice didn’t always have it easy. He never even met his biological father, and whenever his stepfather changed jobs, Ice had to switch schools.

Vanilla Ice / Vanilla Ice and Madonna / Vanilla Ice / Vanilla Ice
Source: Getty Images

He coped with his feelings of loneliness by entertaining and performing. He didn’t do very well in high school and ultimately dropped out without graduating. The main thing that set the teenager apart from his peers was his tremendous musical talent.

Introducing Robert Matthew Van Winkle

In addition to his love for hip-hop, he was a breakdancer and was particularly known for the move “Ice,” which would later become his nickname. He would gather a group of performers called “the Vanilla Ice Posse” and performed with them on the streets and in the nightclubs. But he had another passion, motor racing. In fact, he won three straight titles at the National Grand Championship.

Vanilla Ice backstage at a club.
Photo by Paul Natkin/Getty Images

But he ultimately decided not to do it professionally after dealing with an injury. That’s when the multi-talented star dedicated all his focus to his music career. His debut album Hooked, later reissued as To the Extreme, featured the smash hit single, Ice Ice Baby which is Vanilla’s claim to fame.

He’s His Own Barber

Even at the peak of his extreme fame, Vanilla Ice didn’t trust anyone to get close to his trademark pompadour, which he dubbed “the beak.” The haircut includes shaved lines into the sides and a light stripe whooshing through the front. In order to maintain the look, Ice took a DIY approach.

Vanilla Ice performs on stage.
Photo by Walter Iooss Jr./Getty Images

“I sit where there’s a mirror behind me and hold another mirror in front of me,” he writes. “That way, I can see my whole head.” Ice was obsessed with his locks, and he would get on himself if it didn’t look flawless. “I don’t like being photographed unless my hair is perfect – that’s why you’ll see pictures of me in baseball caps a lot.”

Vanilla Ice Doesn’t Cry

“I don’t cry, and I don’t know why,” Ice revealed. Even when he broke his ankle as a teenager in a motorcycle accident, he didn’t shed a tear. He explained that the only time he ever felt a teary sensation was when he was awarded plaques for his platinum record.

Close-up portrait of Vanilla Ice.
Photo by Walter Iooss Jr./Getty Images

“My eyes got watery… it’s as close to crying as I’ve ever come,” the rapper admitted. I mean, it’s good to keep your emotions in check, but I think everyone cries, no matter who they are. But I could be wrong; maybe Vanilla Ice really doesn’t cry.

He Got Stabbed in the Butt

As Ice’s popularity skyrocketed, people doubted some of his claims that he was raised in the dangerous parts of Miami and Dallas, where he joined a gang after his stepfather moved the family there for a job opportunity.

Vanilla Ice shows off his knuckle tattoos which spell out “ wide open”.
Photo by Ian Gavan/Getty Images

A lot of people believe that he exaggerated his background to fit a certain image and appear more like a hardcore street urchin. Ice hates that he constantly needs to defend himself and is compelled to pull off his pants to show a scar on his butt that he got from a knife attack when he was 18 years old.

Street Fight Turned Ugly

According to him, he got into a street fight that took a turn for the worse when someone pulled out a knife and cut over his thigh and buttocks. Yikes! The injury required a long hospital stay after he lost four pints of blood. That sounds pretty scary.

Vanilla Ice poses while reaching out his arms and sticking out his tongue.
Photo by Scott Harrison/Getty Images

He wrote, “What I did was put this thing that looked like a Q-tip with alcohol on it down inside my leg to plug up the artery.” At least he didn’t cry, though! This story seems to check out, so people should back off. It can get annoying to feel like you’re always defending your past.

He Wore Outlandish Outfits to School

As he was growing up, Ice bounced around from school to school and admitted that he didn’t have much interest in formal education and wasn’t thrilled to be the new kid all the time. In order to distract himself from that sense of isolation, he started showing up in insane outfits, including mismatched shoes.

Vanilla Ice is wearing knee-high socks, a skirt, a t-shirt, and a hat in his high school yearbook.
Source: Pinterest

“I’d wear a boot on one foot and a tennis shoe on the other,” he said, “wear blue jeans with one leg long, the other leg cut off, stuff like that.” I think most of us mismatch our socks, but shoes are a whole other story. But I respect people who have the guts to dress so outlandishly in public.

If He Had a Problem, He Solved It Himself

Ice maintains that he was never one who felt comfortable sharing his feelings. His mother explained that when Ice was only eight, she tried to put him in therapy to help with his troublemaking ways at school. But Ice refused to talk. Some people just aren’t very comfortable with their feelings.

A photo of Ice as a toddler eating a donut.
Source: Pinterest

“I never needed to talk to anyone to solve my problems,” he writes. “A lot of people need someone to talk to, but I’ve never been able to open up and do that. Never could, never will. That’s just the way I am. And that’s just exactly where the ‘Ice, Ice Baby’ hook came from – ‘if there was a problem, yo, I’ll solve it.”

Sometimes He Used Dirty Words

Participating in rap battles growing up, Ice would sometimes deploy some profanity. It wasn’t something he necessarily wanted to do, but his competitors were, and Ice felt like he needed to keep up if he wanted to make this a career.

Ice is doing pushups on stage during a performance.
Photo by John Atashian/Getty Images

“The thing is, I wouldn’t do it unless some other rapper started cursing and dissin’ me, and the crowd started liking it,” he writes. “’Cause if the crowd starts liking the cursing part, that means to win, you’re going to have to curse back at them.” In his book, Ice added that the reason the raps on the records were clean was that “I don’t need to put in dirty words to express myself.”

First, He Was Vanilla M.C.

Ice started off performing at a dance club in Dallas called City Lights, owned by future manager Tommy Quon. Since “Robert Van Winkle” didn’t quite have an appealing ring to it, Ice decided to go by his teenage nickname that was given to him when he was rapping and beatboxing in the neighborhood – “Vanilla M.C.”

Ice walking in the streets.
Photo by Robin Platzer/IMAGES/Getty Images

But Quon pointed out that there were already a lot of “MCs” in the music industry, such as M.C. Hammer and Young M.C. “You know, your raps, your rhythms are really smooth, smooth as ice, in fact,” Quin said. Explaining that “it sounded okay to me,” Vanilla M.C. officially became the Vanilla Ice we all know now.

He Likes Women for Their Looks

Ice isn’t one to sanitize his image for the masses. In fact, he unabashedly admitted that his main concern when dealing with women is whether or not he finds them good-looking. “My first impression of a girl, whether I’m going to be drawn to her not, is based on her looks. I know it’s not fair, but then I see what her personality is like.” At least he is aware of how shallow he is…

Vanilla Ice poses with a large group of women at a club.
Source: Twitter

Once he finds a woman who can stimulate him intellectually while still “dressing super-sexy,” Ice is a happy camper. He likes taking them to nice restaurants – not too lavish, though: “I like candlelit romantic restaurants, but not those where the menu is so fancy that I don’t know what I’m ordering.”

He Almost Appeared in A Nightmare on Elm Street

After the success of To the Extreme, Ice’s career could have gone in a number of different directions. He made a cameo appearance in a Teenage Mutant Ninja Turtles sequel and then had a starring role in 1991’s Cool as Ice.

Ice performs on stage with the Teenage Mutant Ninja Turtles.
Photo by Matthew Eisman/Getty Images

In between those two projects, Ice was offered a small guest appearance in A Nightmare on Elm Street sequel, to be murdered by Freddy Kruger, “but I didn’t have room in my schedule to take time off for it.” Although we associate Vanilla Ice as a musician, he does have some acting chops.

A Satanist Stalked Him

Another random and strange fact about Vanilla Ice is that he was stalked by a Satanist. In the 1990s, at the height of Ice mania, the rapper revealed to Rolling Stone that he was being followed by a woman who was trying to convert him to Satanism.

Ice holds up his hand to the camera.
Photo by Michel Linssen/Redferns/Getty Images

Ice first encountered the woman at Wembley Stadium, where she flashed him in a trench coat. That should have been the first red flag. That same woman later followed him all the way to Japan and slid a book under his hotel door, a Satanic Bible with a personal message to Ice to join the flock. Why was she specifically after Ice? Because his birthday is on Halloween.

Did He Steal the Melody From “Under Pressure”?

He absolutely did, although he tried to deny it at first. There is actually a lost interview (that isn’t on YouTube and nearly impossible to find on the internet) where Vanilla tries to explain that the songs aren’t exactly the same because he added a note. He even attempts to sing parts of both songs to prove his case – but the songs even sounded identical when he sang them.

David Bowie talks to Freddie Mercury.
Source: Pinterest

Freddie Mercury and David Bowie ultimately sued Vanilla Ice. The case never made it to court – which is probably a good thing. Vanilla ended up settling for an undisclosed amount, and songwriting credits on Ice Ice Baby went to Mercury and Bowie.

Did Kids Notice He Rapped About Guns and Cocaine?

As someone who knew every word to Ice Ice Baby when I was in middle school, I think I can speak for all kids out there when I say… no! We were just rapping along, and our naïve minds didn’t understand that we were making references to guns and cocaine the whole time.

Vanilla Ice is performing at club CBGB.
Photo by Bill Tompkins/Getty Images

“Shay with a gauge and Vanilla with a nine / ready for the chumps on the wall / the chumps acting ill because they’re full of eight balls” didn’t really mean anything to us. I was just proud I memorized all the words, and paid no attention to what I was actually saying. But maybe some kids were less innocent than I was and understood.

Why Does He Say “D-Shay” Instead of “DJ?”

In one line, the lyrics go, “check out the hook which D-Shay revolves around it.” So, why does he say “D-Shay” instead of DJ? Apparently, it’s a reference to one of his friends D-Shay who happened to be a DJ early in his career. D-Shay gets plenty of shoutouts during the show, like where he sings “Shay with the gauge” or “Shay plays the fade.”

Vanilla Ice performs on stage.
Photo by Robert Lachman/Los Angeles Times/Getty Images

However, it stands out more in that particular line because you expect him to say “DJ” like in the previous verses. The true Vanilla Ice fans know when to switch from “DJ revolves it” to “D-Shay revolves it” while rapping along.

What Ever Happened to D-Shay?

Right before Ice Ice Baby became a big hit, one of the co-writers of the song, Vanilla Ice’s DJ friend named Earthquake, got in a physical altercation with D-Shay. Apparently, everyone, including Vanilla Ice, took Earthquake’s side and stopped talking with D-Shay.

DJ Curly and D-shay pose together.
DJ Curly, D-shay. Source: Tumblr

It’s sad that they no longer talk, but the shoutout didn’t go anywhere. It will essentially keep D-Shay relevant forever. I tried to see what D-Shay is up to now, but it looks like he is laying low. I couldn’t really find anything about him in recent years.

Why Did Suge Knight Want to Kill Him?

Suge Knight dipped his toes in the Ice Ice Baby pot, although it’s still unclear how exactly. Legend has it, one of his employees claimed he had a hand in writing it, so Suge did the only rational thing – he took Vanilla Ice onto a hotel balcony and threatened to throw him off if Vanilla didn’t cough up some cash.

Suge Knight at the Shore Club.
Photo by Johnny Nunez/WireImage/Getty Images

Vanilla ended up forking over a huge chunk of money to Suge. Again, it’s not clear why. But it sounds like some kind of mob protection racket to me. Vanilla has since claimed in multiple interviews that he is fine, and the reason he gave Suge millions of dollars – which he used it to launch Death Row Records. That means Vanilla is partly responsible for Snoop and Tupac going mainstream.

The Video Was Not Filmed in Miami

If you grew up in Miami, you might have noticed something out of place in the music video. As a Florida native myself, I was disappointed to find out that the video wasn’t actually filmed there, like, not even one scene.

Ice is dancing in the music video.
Source: YouTube

In fact, the entire video was shot 1,300 miles away in Dallas and had a budget of $8,000. After watching the video, I can’t help but wonder where all that money went. It features some of the worst blue screen removals to ever go public, and it makes a local weather report look like 300. Just rewatch it and see for yourself.

A Monumental Moment in Hip-Hop

It’s hard to believe decades later, but Ice Ice Baby made history when it was the first-ever rap song to make it to number one on the Billboard charts. Ice Ice Baby gets credit for making rap more mainstream than ever.

Vanilla Ice is showing off his new cd.
Photo by M. Caulfield/WireImage/Getty Images

But here is a little bit of trivia that people generally forget. While it is certainly the first number one hip hop song, it was the third one that included rapping – or sustained rhythmic talking… however you want to put it.

All Three Had White People Doing the Rapping

As the third Billboard hit to feature rapping, it came right behind Blondie’s Rapture and Pet Shop Boys’ West End Girls. Another interesting fact about these billboard number one hits is that all three featured white people doing the rapping.

Debbie Harry of Blondie / Chris Lowe and Neil Tennant of The Pet Shop Boys.
Photo by Brian Cooke, Redferns, Getty Images / Lester Cohen, Getty Images

Which begs the question, what’s the first hip-hop song featuring black people rapping? It depends on how you define hip-hop. But it’s either C + C Music Factory Gonna Make You Sweat (Everybody Dance Now) from 1991 or Kris Kross’s Jump in 1992. Right Said Fred squeezed in between with I’m Too Sexy for yet another white rapping number one hit.

Did He Borrow It From a Black Fraternity? Or Vice Versa?

The Alpha Phi Alpha fraternity is known for their famous chant that goes “Ice ice baby, too cold, too cold.” It isn’t exactly confirmed whether Vanilla Ice took the phrase from the Alphas or the other way around. I mean, most people would suspect that the fraternity probably took the famous line.

Members of the Alpha Phi Alpha fraternity pose for a photo.
Source: Twitter

However, Vanilla Ice (and that song in particular) does have a history of plagiarism. My nerdy mind immediately thinks this is a total “Brrr; it’s cold in here, there must be some clovers/toros in the atmosphere” moment.

Before He Was a Rapper, He Was a Break Dancer

At the tender age of 13 years old, Vanilla Ice learned to break dance and loved it. His new hobby landed him in a break dancers’ group; as the only Caucasian member, he was dubbed with the nickname “Vanilla.” Although he wasn’t a fan of the name, it kind of just stuck after that.

Ice is taking part in a breakdance battle.
Source: YouTube

It didn’t take long for his impressive dance moves to catch the attention of many. But the rhymes soon followed, and a career in show biz looked like an option. But if he wasn’t a rapper, Vanilla Ice just might be entertaining us as a dancer.

Meeting His Manager Was a Lucky Break

Before he became a household name, Vanilla Ice spent a lot of his time hanging out in City Lights, a local Dallas nightclub where he would often perform. Being a more specific demographic, Vanilla Ice really stood out at the venue.

Vanilla Ice is performing at a club.
Photo by Bill Tompkins/Getty Images

Along with his fast-moving dance feet and his ability to put quick rhymes together, the club owner, Tommy Quon, noticed something special about the performer. It didn’t take long for Quon to become his very first manager and he did wonders for Ice’s career. It really was fate that these two found each other.

Ice Ice Baby Came From His First Album

In 1989, Vanilla Ice’s first album, Hooked, was released. The vast majority of mainstream listeners weren’t even aware of the album, but that was about to change. The song that was included on that album was Ice Ice Baby, and it featured a hook from the David Bowie and Queen’s smash-hit “Under Pressure.”

Vanilla Ice attends the American Music Awards.
Photo by Ron Galella, Ltd/Ron Galella Collection/Getty Images

Once the song was played on a Georgia radio station, people became intrigued. Who is this unknown, talented artist with the catchy lyrics? It didn’t take long for the entire world to find out. It was almost like overnight stardom for the rapper.

He Made a Cameo in Teenage Mutant Ninja Turtles II: Secret of the Ooze

If you’re a nineties kid like me, you remember when the Teenage Mutant Ninja Turtles were the big thing. The franchise was a massive hit with kids in America and is still considered a favorite of the last thirty years. If you watched the second film, you probably noticed a cameo from a famous rap star.

Ice poses with the Teenage Mutant Ninja Turtles.
Source: Twitter

At this point, Vanilla Ice was dominating the music scene. Just two years after Ice Ice Baby was released, it looked like the rapper was transitioning into films. Although it was a small role, it was certainly a memorable one.

He Released a Memoir

With incredibly popular songs like “Play That Funky Music” taking over the music charts and a film credit in a successful movie, Vanilla Ice proved he is more than just a double threat. He took his talents and became an author. We already know he is a skilled writer, so why not become an author?

A copy of Ice’s memoir.
Source: Pinterest

In 1991, Vanilla Ice released his official biography entitled Ice by Ice. But some of the claims the rapper made in his book (and interviewed) raised some eyebrows. Fact-checking press wondered if he was telling the truth. That’s when Vanilla Ice realized the serious allegations that come with stardom. Reaching the top comes with a price.

His Credibility Was Questioned

His memoir included some not-so-certain tidbits and some interviews that don’t exactly match up with all the facts, and many folks suddenly questioned Vanilla Ice’s credibility. He put the blame on his manager and continued to make excuses about why his memories weren’t exactly what fact-checkers were able to dig up.

Vanilla Ice performs for fans at a football game.
Photo by Scott Halleran/Getty Images

There are some mistakes that even the greatest PR representatives cannot fix. He learned the hard way that once credibility is gone, it is much harder to be trusted and get back in the adoring public’s good graces.

His First Feature Film Wasn’t the Hit He Expected

Many people started wondering if Vanilla Ice was too overrated. In the early ‘90s music scene, groups were getting turned down because of their boundary-pushing lyrics. Sadly, it was no big surprise that movie number two wasn’t as big of a hit for Ice.

Ice and Kirstin Minter in a still from Cold as Ice.
Source: Pinterest

In 1991, he took on the lead role in Cool as Ice, but it ended up being a commercial flop. The film earned less than one million dollars at the box office. Ice was at the start of his fame and wasn’t ready for it to fade. Would he be a one-hit-wonder?

He Had a Thing With Madonna

Ice publicly revealed that he was drawn to beautiful women. So, of course, it comes as absolutely no surprise that he got with the Material Girl herself. Madonna was one of the biggest stars in the world in the early ‘90s, and her dating life was no secret.

Vanilla Ice and Madonna stare into each other's eyes.
Source: Moviestillsdb.com/Copyright: Warner Books

She and Vanilla began dating and were together for about eight months. They were seemingly happy together until Vanilla ended things with her. He said that the reason behind their relationship ending was the release of her controversial book.

Vanilla Ice Was in Madonna’s Book “Sex”

Just to put this into context, Vanilla didn’t split with Madonna because her book was met with controversy; it was the actual content of Madonna’s coffee table book titled Sex that he had a problem with. The book was released in 1992 and shocked the world.

Madonna bites on Ice’s necklace.
Source: Moviestillsdb.com/Copyright: Warner Books

The book included sexually suggestive and even pornographic images of several sexual acts. Featured in the book were celebrities including Isabella Rossellini, model Naomi Campbell, rapper Bug Daddy Kane, and rapper and then-boyfriend Vanilla Ice.

Only He Could Touch “The Beak”

One of the many things Vanilla Ice is known for is his haircut. His pompadour with shaved lines was called The Beak. Ice was so worried about always having his hair look precise, so he decided to become his own barber and taught himself how to groom it.

A photo of Vanilla Ice.
Photo by Ron Galella, Ltd/Ron Galella Collection/Getty Images

This guy was so obsessed with his hair that he wouldn’t go out in public with less than perfect. A bad hair day meant wearing a hat. This is why he was often pictured in baseball caps. There are many 1990s trends we would love to see come back, but this is definitely not one of them.

Hard to Swallow

In 1998, Republic Records released the album Hard to Swallow, and it was recorded after the rapper’s four-year music hiatus. It was a heavy metal/ hip hop mix, and it attracted a brand-new fan base and gained much media attention.

Vanilla Ice performs on stage.
Photo by C Brandon/Redferns/Getty Images

However, reviews of his metal music attempts were met quite negatively. He is multi-talented with acting, dancing, and author credits under his belt. But when it comes to his main passion of music, he should stick to what he does best – hip hop.

His Passion for Home Renovations

When he was still a teenager, the young Vanilla Ice started flipping houses, a real estate business venture when someone buys a cheap house, renovates it, and then sells the new and beautiful home at a higher value. If you know what you’re doing, this could be a very profitable career.

Ice poses outside his home.
Source: The New York Times

Shortly after, he began getting into remodeling projects; this included his own Miami Beach mansion. In 2010, his passion for home renovations turned into a television show called The Vanilla Ice Project. Some people really can do it all.

Vanilla’s Personal life

Vanilla Ice’s most public relationship was with Madonna. But the Hollywood It Couple called it quits less than a year after they started dating. In 1997, Vanilla Ice tied the knot with Laura Giaritta, and they have two beautiful daughters together, Dusti Rain and KeeLee Breeze.

Vanilla Ice and his wife Laura Van Winkle arrive at an event.
Photo by Ethan Miller/Getty Images

Ice describes himself as a “Juggalo” and he enjoys Psychopathic Records hip hop groups. He is also a vegetarian, which was only supposed to last three months but continued after he noticed positive changes in his body. In 2016, his wife filed for divorce, citing that their relationship was “irretrievably broken.” He had a third child in 2018 with his new wife.

Just an Ordinary Guy

The infamous rapper transformed himself into a lighting salesman. Yes, you heard that right. I guess when a rap career starts to fade, you have to find a way to shine again. Since he had so much talent, it’s interesting that he chose this path.

Vanilla Ice performs on stage wearing crazy clothes
Photo by Jim Steinfeldt/Michael Ochs Archives/Getty Images

Mr. Vanilla Ice is currently working at Capital Lighting in Florida. He also designed a line on chandeliers which is called “Vanilla Ice Lighting.” It’s a good way to capitalize on his name, even if he doesn’t want to turn the lights of his rap career back on.