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Rapper Vanilla Ice (born Robert Matthew Van Winkle) made a gigantic splash with an album titled To The Extreme (1990), which sold an astounding 11 million copies. It featured the chart-topping single, “Ice Ice Baby,” which some observers believe propelled hip-hop music into the cultural mainstream.

With his chiseled good looks and abundant vocal skill, Ice had star quality that was potent—but the rapper ran into problems on the business side of his career. He inked a contract with SBK Records that, in retrospect, seemed to ultimately hinder his success.

SBK allegedly wanted Ice to adopt a different look. They also reportedly concocted biographical information that was supposedly used without him being aware of it or consenting to it.

The upshot was that his popularity with fans nosedived. The Vanilla Ice they loved and whose albums they bought as fast as they could had morphed into someone who did not appeal to them the same way. The magic was gone. That issue, coupled with his reported drug abuse, sent his career into a freefall.

What is Vanilla Ice doing now? Has he recovered from the earlier missteps in his career, ditched his reported drug use, and gotten back to what made him a music industry phenomenon? Here’s what we learned.

His Musical Career Faltered In The 2010s

The 2010s were not a good decade for Vanilla Ice compared with the years of his earlier fame. After his unfortunate business deal, the rapper spent much of his time trying to rediscover a formula for success.

Not all of Vanilla Ice’s woes came from his recording label, however. Drugs undermined his career as early as the 1990s.

You know that something is seriously amiss when an article begins with the sentence, “Mentioning the name Vanilla Ice usually elicits looks of disgust, mistrust, and runaway cheeseball feelings,” as an October 1998 story in Miami Music did.

The article alluded to Ice’s reported drug use during that period, including an alleged heroin overdose. He got so many tattoos when he was seemingly under the influence that he said he lost track. “I didn’t even realize how many I was getting…” he admitted.

His indulgence in harmful substances sounds like it barreled alarmingly out of control.

“I was puking and sh*tting on myself, and man it was ugly,” Ice acknowledged. “People were throwing cold water on me, and when I woke up, I thanked God I was still alive and promised Him I’d turn myself around. Ever since then He’s been blessin’ me.”

He released some independent albums in the 2000s and early 2010s, but they seemed like shots in the dark so he could regain his professional footing and were largely drubbed by critics. Vanilla Ice’s last studio album, WTF, was released in 2011.

He performed at the Houston Texans’ halftime show on September 15, 2013. The NFL team had a dreadful skid after that, losing 14 games. Some players even speculated that Ice’s appearance had jinxed them (per Fox Sports).

He Stepped Back from Music To Focus On Motocross And Jet Skiing

After a few difficult years both personally and professionally, Vanilla Ice took a break from the music industry and went back to his other loves: motocross and jet skiing. It was a career and lifestyle shift that Sports Illustrated claimed brought the troubled rapper “peace and fulfillment.”

“I don’t need artificial highs anymore,” he said. I’m sober.” Vanilla Ice confirmed that he had cleaned up his act a lot since his days of using heroin. He said that he only smoked marijuana occasionally and sometimes had a few swigs of the herbal liqueur Jägermeister.

“One of the most ridiculed musical performers of all time,” who once got lumped into a category of passe performers along with Tiny Tim and Milli Vanilli, was at last treading a new and healthier path.

He even reportedly scuttled most of the vestiges of his old rapper image. He was a motocross maniac who couldn’t get enough of it, a passionate pro who “lives for motocross.”

“This is the ultimate rush,” Ice declared. “It’s a great way to shut your mind off to the real world and just ride and feel the explosiveness.”

His prowess for motorbike racing emerged when he was a teenager winning trophies right and left and establishing his reputation. But Vanilla Ice’s demons got the best of him. Becoming ultra-famous and in demand because of his music swept him away. It’s heady stuff for a young man and he understandably fell victim to its allure.

“You’re a kid, and everybody wants you,” he explained. “The drugs, the women, the money—everything was right there in front of me. It affected me. It would affect anyone.”

There were other consequential missteps. Ice claimed that in 1990, his manager, Tommy Quon, reportedly disseminated biographical information about him that greatly exaggerated his accomplishments in motocross racing and contained false statements about his background.

Quon claimed that the information originated with Ice himself, an assertion the rapper denied. Regardless of the source, the damage was done.

After a failed suicide attempt on July 4, 1994, Vanilla Ice turned to jet skiing to pull himself out of the doldrums—and it seemed to work. According to Sports Illustrated, “By the summer of ’95 Van Winkle was the world’s No. 6-ranked sit-down Jet Ski racer, competing nearly every weekend and earning Kawasaki sponsorship.”

In 1996, he extended his reach even further, opening 2 The Xtreme in Miami Beach, a store that specialized in alternative-sports equipment and gear. Motocross intrigued Vanilla Ice again, so he tried out for ESPN’s X Games in the motocross freestyle division in 2002. He didn’t make it, edged out by younger, fiercer daredevils.

He Forged A Second Career In Reality TV

Maybe reality TV appealed to Vanilla Ice’s flamboyant, dramatic side. Perhaps he just wanted to try something different. Whatever the impetus, he staked his claim in the reality TV world by battling Todd Bridges on Celebrity Boxing under the handle “Bi-Polar” in March 2002 on Fox.


That matchup didn’t work out the way he hoped, however. According to Sports Illustrated, Ice was a bit cavalier about the whole thing. “I thought it’d be easy money, just a show,” he said. “I didn’t think I’d have to train. They told me it was an exhibition.”

On top of that, he acknowledged going “out on the town” with Bridges the night prior to their contest and smoking a joint. Not surprisingly, Ice quickly went down to defeat in three rounds.

His stint on TV had not ended, though. The following year, he was on three episodes of Celebrity Bull Riding Challenge, five episodes of Hollywood Squares, and eight episodes of The Farm. In early 2004, he turned up on The Surreal Life.

Ice got his own TV gig that tapped into his expertise in real estate flipping and home improvement on the DIY Network, debuting in 2010. This time, he was successful.

The Vanilla Ice Project aired for nine seasons and garnered accolades like the Hermes Platinum Press Award, the Telly Award, and the Factual Entertainment Award. He also had a website, Vanilla Ice Real Estate, that offered real estate tips to the public.

He showed off his skill as a hoofer on season 23 of Dancing with the Stars. Even though he was eliminated on October 4, 2016, Vanilla Ice expressed gratitude for his opportunity to be on the show. “Dancing makes you happy and it’s just a happy experience,” he said (per ABC). “I’m honored to be here.”

He’s Done Some Acting

With his flair for theatricality and showmanship, Vanilla Ice seemed like a natural for acting. He tested out his aptitude for being a thespian on The New Guy in 2003 when he had a cameo as a music store employee.

Ice appeared as a fictionalized version of himself in the film That’s My Boy (2012) alongside stars such as Adam Sandler, Andy Samberg, Susan Sarandon, and James Caan.

Although it may seem like a big stretch, Vanilla Ice also played The Adventures of Tom Sawyer author Mark Twain in a Western comedy, The Ridiculous 6 (2015), with Adam Sandler, Nick Nolte, and David Spade.

He did another acting turn as himself in The Wrong Missy (2020). In 2022, he narrated a 30-minute film called Booking Sounds 2.

He Was Charged With Grand Theft In 2015

In 2015, CNBC reported that Vanilla Ice was arrested and charged with reportedly stealing items from a foreclosed home in Lantana, Florida, including bicycles, furniture, and a pool heater. According to NBC News, Vanilla Ice called his arrest “a misunderstanding” and “blown out of proportion.”

He claimed that the items in question got abandoned on a curb and “he thought they were trash.”

Prosecutors reportedly said that within one year, they would drop the charges as long as he complied with two conditions: paying $1,333.39 to the homeowner’s estate and putting in “100 hours of community service with Habitat for Humanity in Palm Beach County.”

His Wife Filed For Divorce In 2016

He found himself dealing with problems on the home front as well. His wife, Laura, whom he wed in 1997, filed for divorce in 2016. They had been living apart since 2011 and shared two children together.

“I gave myself a birthday present,” Laura said, according to the Miami Herald. “I wanted to file for divorce for a long time but I was scared to do it, so I figured I’d do it on my birthday.”

The marital matter got contentious when Vanilla Ice countersued, asking for equal custody of the children and refusing to pay alimony, which his wife wanted. If his wife put up a legal fight, Ice reportedly expected her to take care of his attorney’s fees as well.

He stayed tight-lipped about his marriage meltdown. He said, “That’s a private family matter, and it’s no one’s business.”The divorce between the warring Van Winkles was finally settled in 2019.

He took to Twitter to announce the birth of his baby in 2018, captioning a sweet pic of the child, “My little #IceIceBaby.”

He’s Dipped His Toes Into Entrepreneurship

Vanilla Ice has certainly been busy branching out. He has had his hands full with new ventures plus concert appearances.

In 2013, he started a pricey line of interior lighting fixtures that built upon his passion for real estate and home renovation.

He linked up with the Joyburst brand for a ’90s-inflected healthy energy drink called Vanilla Ice. He told Rolling Stone that it is “fun and delicious.”

Speaking of tasty beverages, Ice founded a tequila company called Naked Diablo Tequila in December 2022. He posted on Instagram, “Say hello to my new tequila company. Make a Diablo. This is the game changer when it comes to tequila.”

According to his own website, Ice will portray a character named Hielo in a video game called Crime Boss: Rockay City.

Ice has also been performing at private events and with the I Love The ‘90s tour in the United States and Canada along with other throwback acts like All-4-One.

Vanilla Ice experienced dazzling success in his musical career until it cratered. He has done a remarkable reset of his brand since then, putting all of his interests and aptitudes to use in business, competitive sports, television, and films.

Ice is like a prize fighter who stubbornly keeps getting up off the mat and just won’t be counted out. This resilient celebrity whose heyday took place in an earlier era definitely can’t be written off just yet!