The (Mostly) True Story of Vanilla Ice, Hip-Hop, and the American Dream

I think I know enough of hate
To say that for destruction ice
Is also great
And would suffice

—Robert Frost, “Fire and Ice”

“Robby Van Winkle and Vanilla Ice are the American dream come true.” —Vanilla Ice, Ice by Ice

I. Something Grabs a Hold of Me Tightly

Vanilla Ice was discovered on Martin Luther King Jr. Boulevard. It was the winter of 1987-88 in South Dallas, or maybe it was the following summer. All exact dates have dissolved into a haze of liquor, hair spray, and the tinnitus caused by long-gone 808 claps. The only thing anyone can agree on is that at the height of hip-hop’s first Golden Age, all the action in the Triple D went down at a club called City Lights.

The property had already weathered several boom-and-bust cycles. Originally a segregated postwar movie palace christened the Forest Theater, it was alternately transformed into a jazz cellar, a recording studio, and the stage for legendary seances by B.B. King, Wilson Pickett, and Prince. By the end of Reagan’s second term, a local entrepreneur named Tommy Quon had resurrected it as the hip-hop epicenter of North Texas. From Thursday night until the break of dawn Sunday morning, the dance floor rumbled with a thousand rowdy but chic revelers. They freaked and hit pop locks, the Roger Rabbit, and the wop. The walls shook from Whodini, LL Cool J, Too Short, N.W.A, and the DFW’s own Fila Fresh Crew. Late at night, when you could feel the bass deep in your sternum, the spot would erupt to the seismic shake of Nemesis’s regional anthem “Oak Cliff.”

The ballers, hustlers, and dope dealers of South Dallas coexisted in uneasy communion. B-boys and D-boys intermingled with models and around-the-way girls. No evidence exists that Roy Tarpley was ever in attendance, but I’d bet on it. This was the heart of South Dallas, the trenches. Tussles were frequent, and being Texas, half the club came strapped. It was no place for the meek, but without risk, there is no reward. In the DJ booth was the surgical turntablist Floyd “Earthquake” Brown, who spotted something out of the ordinary one Saturday evening.

“I noticed this white guy dancing in the crowd,” Brown says. “City Lights was all Black, so at first I was like, ‘What does he think he’s doing?’ He could dance his ass off, and we’d never seen a white guy do that. The women was loving it and getting all up on him like, ‘Oooh, look at him.’ And he was like, ‘I’m not finna stop. I’m gonna make y’all love me.’”

In about two years, in September 1990, the anonymous white dancer in the crowd would drop To the Extreme, which would sell 15 million copies worldwide, faster than any album since Purple Rain six years earlier. Its inescapable lead single, “Ice Ice Baby,” became the first rap song to top the Billboard Hot 100 and accelerated the genre’s crossover into the American mainstream. There were Vanilla Ice dolls, a ghostwritten autobiography, a Scholastic book with MC Hammer, rock ’n’ roll comics, and a board game that came with a toy boom box; a Vanilla Ice movie and cameos in both Madonna’s Sex book and the Teenage Mutant Ninja Turtles sequel. The first white solo rapper to become a pop star would have one of the most dizzying ascents and precipitous downfalls in music history. At 23, he was briefly the biggest rapper in the world and the public enemy of hip-hop purists—the subject of (still ongoing) debates about appropriation and authenticity. But before any of that could transpire, he had to win over the doubters in South Dallas.

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The story of Vanilla Ice has long been shrouded in a fog of shoddy reporting, breathless tall tales, and harmless self-deception. A white rap Rashomon, if the bandit battled Bebop and Rocksteady. Everyone’s narrative is slightly askew, which adds to the charm. You would just print the legend if you could figure out exactly what it is.

Here are the basics: Vanilla Ice was born on Halloween in 1967, most likely in Dallas, though the first chapter (“Ice Formations”) from his quickie Avon Books memoir, Ice by Ice, claims he entered the world in a Miami suburb. His biological father was never in the picture. The unfortunate last name, Van Winkle, was bequeathed by the man his mother was married to at the time of birth. By the time the future Ice was 4, the elder Van Winkle had departed, leaving Ice’s single mom, a piano teacher, to raise him and his older half-brother. For the next dozen years, the family shuttled between diverse neighborhoods in Dallas and Dade County, where his new stepfather, Ecuadorian immigrant Byron Mino, worked at a Chevrolet dealership.

After fame hit, Ice was attacked for claiming Miami as his hometown. But that was only slightly different from the approach taken by fellow Dallas native the D.O.C., who wore Raiders hats while signed to Ruthless Records. In late-’80s rap, modern-day capitals like Houston and Atlanta were considered provincial backwaters. Claiming Dallas was a commercially fatal proposition. “Respected” rap came from New York and maybe Philly. Few took L.A. seriously until The Source put N.W.A on the cover in 1989, and even then, they shared the honor with Oakland’s Too Short, largely considered a profane novelty east of Kansas City. The lone exception was Miami, home of the banned-in-the-USA Uncle Luke and the bass sound that owned the Southeast until Outkast debuted.

“I lived in Miami and wrote ‘Ice Ice Baby’ about it. I didn’t think about where I was from at the time. That only became a thing after I was famous,” Ice tells me. “I was like, ‘Where I’m from? Who fucking cares where I’m from?’ I was embarrassed to tell people I was from Farmers Branch [an inner-ring suburb of Dallas]. I didn’t tell them I was from Miami. I didn’t tell them I was from anywhere. I was just like, ‘Listen, I’m from around the corner, man. I’m from around the fucking way.’ I actually tried to detour people.”

Photo by Acey Harper/The LIFE Images Collection via Getty Images/Getty Images

Ice and I speak during a two-and-a-half-hour Zoom call in September. He dials in from the private theater inside his massive Florida rococo mansion, near Palm Beach. The estate contains 24-karat chandeliers, a lounge with platinum plaques, and a life-size Raphael from the Ninja Turtles; there are gilded ceilings, a quarter-million dollars’ worth of marble, and a custom-made pool designed to channel the turquoise waters of the Bahamas. It is exactly the house that you’d expect Vanilla Ice to have. He shrewdly invested his “Ice Ice Baby” money, parlayed it into a fortune flipping real estate, and capitalized on that via The Vanilla Ice Project, a reality show that has aired for nine seasons on the DIY Network and turned him into hip-hop’s Bob Vila.

When you talk to Vanilla Ice, you quickly realize that it was more than just privilege and luck that led him to stardom. He’s a master storyteller: charismatic, generous, and perceptive. The work ethic, self-belief, and sense of humor that allowed him to survive the withering backlash were there from the start. There is also the endearing charm of a lifelong hip-hop and funk obsessive. His eyes light up at the mention of onetime labelmate Willie D of the Geto Boys, and he starts reflexively rapping the hook to the flagrantly obscene “Bald Headed Hoes.” Ice rhapsodizes about the genius of L.A. electro-rap pharaoh the Egyptian Lover and describes his first concert, Roger Troutman at City Lights, with apostolic fervor. But his epiphany arrived in 1984, when Breakin’ converted him to the fluorescent gospel of the four elements.

“I can’t tell you how many sleepless nights I’d stay up and mimic the moves from Breakin’ and Beat Street,” Ice says. “Watching them dance with the broom, the fishing line, doing the robot, and then throwing in my own moves. My mentality was always, ‘No matter what it is, you have to prove yourself.’”

Forming a crew, the kid nicknamed Vanilla made $40 a day breakdancing, beatboxing, and freestyling over Mantronix beats at local malls, a form of hip-hop busking that seemed exotic to well-heeled Dallasites buying loafers at Neiman Marcus.

“I had my big ghetto blaster sitting there and a microphone connected to it. It was all distorted because I had it cranked to 10, and I’m like, ‘This is my dancer E-Rock. Give it up, he’s going to do the windmill. Bam!’ Then he’d bust it out,” Ice says. “Eventually, I started to rap like, ‘Aye, you heard me write a rhyme / You heard me bust a beat / Now check this out / Because I’ma move my feet.’ Next thing you know, I didn’t want to put that microphone down.”

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Hip-hop is now the nucleus of modern pop culture and everything is accessible via Google, so it’s difficult to remember when it was an underground subculture accessible only via hard-to-find 12-inches, “How do you do fellow kids” trend reports, and a handful of rapsploitation films. Until Yo! MTV Raps premiered in 1988, it was rarely seen on TV; urban radio station programmers largely dismissed it as an unmusical fad.

In Dallas, a nascent hip-hop culture began to flourish in the late ’80s. Everything revolved around the DJ, and the Mount Rushmore of the old school were DJ Ushy Epon (“Mr. Funk ’n’ Roll”), Earthquake, DJ Rock of the Fila Fresh Crew, and DJ Snake, the producer who weaponized Nemesis. By the time Vanilla Ice first electric-boogaloo’d into City Lights, heads in the Metroplex were already locked into the city’s first all hip-hop show, The All Hardy Def Party on KNON-FM. The West Dallas Rockets had begun to build their legend as the South’s version of the Rock Steady Crew. The conditions seemed ripe for the city to become the mecca of Texas hip-hop.

At least that was Tommy Quon’s plan. Raised in the Mississippi Delta around blues and soul musicians, the son of Chinese immigrants naturally segued into the world of club ownership, music management, and eventually, the Ultrax label—his attempt to tap into the vibrant Dallas scene. Quon began holding talent competitions to boost business at the club on slow nights. Rock bands, comedians, singers, rappers, and dancers turned out, lured not just by the free gear that went to the winner, but also the grander promise of being spotted by talent scouts and A&Rs—a huge deal in the pre-digital world.

By this point, “Vanilla” had built a rep around Dallas. He’d won regional motocross contests, battled at parties, and become certified on Forest Lane in South Dallas, a place where guys named Robbie Van Winkle did not historically tread. He’d even had a near-death experience after being stabbed five times, causing him to lose four pints of blood and spend several days hospitalized. The attack occurred in relatively safe Richardson, Texas, where Ice went in search of retaliation after someone had jumped his friend. A few years later, he famously pulled down his pants on Rick Dees to reveal the battle scars. In an interview with The Washington Post, Ice alleged that the assailant was a member of a “devil-worshipping posse.” But some of the stories may have appeared slightly … embroidered: At the height of Icemania, he was served with an outstanding warrant for failing to pay fines related to an incident in 1988 in which he “maced a kid in the eyes and beat him over the head in a parking lot.”

“If there was a knock-down, drag-out fight, Ice was right there, ready to go,” Earthquake says. “He wasn’t perpetrating anything.”

Ice was a high school dropout abandoned by his real father, and whose mother was married several times. He grew up lower middle class and toiled away at menial jobs while chasing his dreams—the lone white boy battling in an almost entirely Black environment. The plot of 8 Mile was Vanilla Ice’s story first.

“I had no crystal ball about the future,” Ice recalls. “I just knew that there was an energy around me, and I was going to do something with this. I knew it. There were too many people who liked what I was doing.”

Enter the biopic moment. Too young to legally be in City Lights, the 20-year-old was dared by his friend Squirrel to enter the club’s talent contest. Despite his avowed bad streak, the young Ice loved poetry and says he never drank or did drugs—at least until Squirrel got him wasted on a concoction called the Runny Nose. The liquid courage was all it took. Naturally, it wasn’t like everyone was about to widely embrace him, which means that he had to overcome enough skepticism for a thousand player hater’s balls.

In Ice’s recollection, Earthquake was having none of it. The Vanilla Ice book purports that they nearly came to blows after Ice served him with some freestyle rhymes. The crowd gawked in disbelief. Snickers and laughter rang out; then he went in.

“At first, it was very quiet; you could hear a pin drop. ‘Oh God, what’s this dude going to do?’” Ice says. “I had a little set, and didn’t need much. I could beatbox like a motherfucker, rhyme, and dance.”

He kicked a few bars and segued into a beatbox routine: the Freddy Krueger, the Popeye, and the Sanford and Son, which he described as a drum sound underwater. The crowd started chanting, “Go white boy!” Then he told Earthquake to spin Rodney O and Joe Cooley’s “Yeah Boy,” and busted out a series of dance moves that weren’t replicated by another white person in Dallas until the night that this photo of Steve Nash and Dirk Nowitzki was taken.

“From then on out, all they wanted was more,” Ice says. “I remember this guy laughing his ass off, shocked and entertained that this white boy could do this. Others were like, ‘Damn, I can’t do that. That dude’s killing it.’”

After the show, A&Rs from several major labels handed Ice their business cards. Another audience member was John Bush, the manager of City Lights, who saw something special in the kid from Farmers Branch. Bush eventually became Ice’s road manager and brought him to Quon. Within days, Ice signed a management deal with Quon and became the City Lights resident act, performing nightly five-to-10-minute routines for the packed crowds.

“Ice captivated everybody in the room,” Bush said several years later. “He owned that stage.”

II. I’m on a Roll; It’s Time to Go Solo

With hip-hop growing exponentially, the club had Ice opening up for the hottest acts coming through Dallas: 2 Live Crew, Rob Base, and MC Hammer. In a year, Hammer would have the no. 1 album in the country and invite Ice on the sold-out Please Hammer Don’t Hurt ’Em arena tour. When they first met, though, he was freshly signed to Capitol and yet to release the life-altering “U Can’t Touch This.”

The Oakland rapper was wowed by his future tour mate:

“I was shocked [to see] a white kid who was, no. 1, rapping, and no. 2, dancing,” Hammer said in Ice’s VH1 Behind the Music. “He was playing for a 100 percent Black club, the only white kid in [there]. But that didn’t deter him. He wasn’t trying to emulate dance moves, he was dancing.”

Before signing to a major label, Ice says that he was the “opening act for the opening act for the opener” on the 1989 Public Enemy, Ice-T, N.W.A, and EPMD tour. Backstage, Ice-T told him he was going to make it. In a bizarro “what-if” scenario, Chuck D was so impressed that he attempted to sign him too.

Photo by Walter Iooss Jr./Getty Images

“Ice-T was finishing up with his sound check and was like, ‘What’s this white boy doing out here? Wait, this motherfucker can dance,’” Vanilla Ice remembers. “The next night on tour, Ice-T told Chuck D, ‘Listen, come check out this white boy. You’re going to freak out. This kid can dance.’ It was the dancing that really caught their attention. Even though I was rapping, I don’t think they really heard what I was rapping about. They saw the whole entertainment thing of me onstage and the crowd response—because the crowd loved it.”

At that point, Ice had never seen a white audience. That wouldn’t come until he was already an established mainstream phenomenon. Apart from the Beastie Boys and maybe 3rd Bass, no white rappers had ever performed in front of anything bigger than a keg party—and this one was dancing like he’d personally learned the cabbage patch from the Gucci Crew.

Earthquake remembers when Public Enemy first saw Ice: “Chuck D looked at me and goes, ‘I can make a lot of money off that white boy.’ That’s when it all hit me. Did Chuck D just say what I think he just said?”

The hip-hop world was relatively small back then. Anyone seriously trying to make it invariably crossed paths with everyone else on the circuit. Ice remembers dodging bullets with a pre–“Baby Got Back” Sir Mix-A-Lot after a South Dallas show. The shooter was barefoot, clutching a musket, blasting out the back window of a car. Houston was only a few hours away, so Ice frequently trekked down to rap battles at warehouses in the Fifth Ward, where he befriended Willie D and Rap-A-Lot founder J. Prince.

But until Ice could record a hit, local notoriety could take him only so far. Quon—who declined multiple requests for an interview—had a plan to remedy that, and only had to turn to the DJ booth at City Lights. The East Dallas Earthquake got his start toting records for the groundbreaking Ushy, and quickly graduated to spinning at block parties and long-vanished clubs—as well as making beats for a pre-N.W.A D.O.C. After becoming the resident DJ at City Lights, he signed a management deal with Quon and formed a rap duo with Mario “MC Smooth” Johnson. According to Earthquake, Quon asked whether he and Johnson would help create songs for Vanilla, now rebranded as Vanilla Ice for marketing purposes.

“Mario was like, ‘It ain’t happening. I’m not doing that,’” Earthquake recalls. “‘I was like, ‘[Quon] is putting a lot of money behind [Ice]. I’ll do the music, you write.’ He refused.”

When he made “Ice Ice Baby,” Earthquake was homeless and couch surfing. The introduction of the SP-1200 and the Akai MPC had recently allowed for a quantum leap in sampling. No longer were producers restricted to snatching a guitar squeal or a kick drum—they could loop entire songs. Suddenly, record collections became fossil fuel, and Earthquake immediately turned to the most obvious riff imaginable for a white rapper, Wild Cherry’s “Play That Funky Music.” Unbeknownst to him, it had already been sampled the year before by a group called B.M.O.C., two other white rappers who released a little-heard, Nile Rodgers–produced single on Sire Records.

Trawling through a garage full of dusty records, Earthquake stumbled onto Queen’s Greatest Hits. Nicking “Under Pressure,” Earthquake messed around with the loop for a few weeks before finally laying down drums. The hook was his too—“Ice Ice baby, too cold, too cold”—an interpolation of the Alpha Phi Alpha chant from Spike Lee’s 1988 film School Daze. According to Earthquake, Ice went crazy the first time he heard the beat and hook in its skeletal form, and asked the producer to dub him a tape to ride around with. Earthquake countered that Ice needed to finish the song first. Ice refused. Indignant, Earthquake demanded that Quon erase the beats for “Ice Ice Baby” and “Play That Funky Music.” Earthquake says that a month later he heard the full version of “Ice Ice Baby” on the radio and confronted Quon, to which the manager threw his hands up, apologized, and promised to take care of the enraged producer.

Ice’s memory is slightly different. He claims that he initially wrote the lyrics circa 1988. After moving out on his own, the 20-year-old was broke and back living with his mom. Inspired by a recent weekend trip to Miami, Ice says he wrote it in a half-hour between 12:30 and 1 a.m. Earthquake had sent him a bunch of instrumentals, but he never actually let Earthquake know that he planned on writing to them.

It was the age of fibula-snapping bass, 5.0 Mustangs with the backseats ripped out and replaced by a thundering arsenal of 15-inch Cerwin Vega speakers and dual-voice coil subwoofers. Ice had a 1,000-watt Rockford Fosgate sub stashed in the trunk that made the license plate rattle. Studio time was prohibitively expensive, so he says he started making homemade lo-fi cassettes to sell on Forest Lane, which included a proto version of “Ice Ice Baby” and the never officially released “My Car Goes Boom.” Quon finessed a few free late-night hours in a spot primarily known for car jingles.

“People started liking it, even old people and white people who had never considered listening to rap music,” Ice says. “They’d be like, ‘I know that “Under Pressure,” I used to listen to Queen.’”

From the Bay Area, Quon flew in Vallejo’s Khayree, soon to become a West Coast legend for his production work with Mac Dre, Mac Mall, and Young Lay. The same year that he dropped “Too Hard for the Fuckin’ Radio,” Khayree gave Ice “Hooked” and “It’s a Party.” But no labels wanted to sign a solo white rapper, especially not one from Dallas. After several months of persistence, Quon and Ice procured a deal to release his album, also titled Hooked, on Atlanta’s Ichiban Records, which had quietly released some of the best underground rap records of the era, including ones by Willie D, MC Breed, and Atlanta bass progenitor Kilo Ali.

It’s bizarre to consider that barely a year before becoming a cultural piñata, Ice was a certified South Dallas club phenomenon with the cosign of Chuck D and Ice-T, rhyming over beats from Mac Dre’s producer on one of the most respected independent hip-hop labels. But this was a distinctly different image of Vanilla Ice from the one about to become ludicrously famous, the one rocking shiny suits and parachute pants. Released in late 1989, the cover of Hooked finds Ice crouched on chunks of fake ice, throwing up the set in white jeans, a beeper, and a pink crew neck sweater—predating Killa Cam’s wardrobe by a good dozen years. Behind him, a naked blond throws her head back seductively. He looks like a cocaine-trafficking rapper who Crockett and Tubbs are trying to catch.

“He had a charisma that you don’t see very often,” says John Abbey, the founder of Ichiban, who also helped A&R Hooked. “He was very confident, extremely polite, and had an angle that you didn’t see anyone else doing. It was that simple.”

Except that initially it failed. For four months, the first single, “Play That Funky Music,” was moribund. Without social media to make a song go viral, if radio ignored your first salvo, it often meant your career was over. So Ice, a DJ, and three backup dancers packed into a small van to play a series of promo shows across the South at record stores and sweatbox dives. But it was serendipity that ultimately saved him from the chopping block: A DJ named Darrell Jaye in Columbus, Georgia, flipped over the 12-inch to discover “Ice Ice Baby.” The request lines immediately blew up. Dallas radio ignored it, but it caught fire across the region when Dave Morales in Jackson, Mississippi, threw his full weight behind it.

“We didn’t have a video, so when people heard the song, everyone figured he was Black,” Earthquake says. “Almost no one knew he wasn’t until the video came out. The first million copies must’ve been sold to Black people.”

A million is an overstatement, but Ice says that they sold 48,000 copies on Ichiban in two months, making them an underground success before he ever wore his first pair of harem pants. Yet the madness didn’t really begin until Quon footed the $8,000 budget for the now-immortal video—in which Dallas’s Deep Ellum historic neighborhood stood in for Miami, undoubtedly helping it earn regular rotation on the Box, the Florida-centric video request channel. BET’s Rap City lent early support too.

Offers rushed in from Atlantic Records and Def Jam. But Ice says that as soon as he was about to sign with the latter, a $1.5 million payday arrived from SBK Records, the nascent EMI subsidiary newly flush with Wilson Phillips and Technotronic money. The deal reportedly came about after a young A&R executive, Monte Lipman, discovered “Ice Ice Baby” on a visit to the Jackson radio station and then played it for SBK CEO Charles Koppelman over the phone. Koppelman was so certain that it would be a worldwide smash that he tendered the seven-figure advance before even meeting the rapper.

“Chuck D and Hank Shocklee had told Def Jam about me and I’d landed in New York City ready to sign with them,” Ice says. “Then I got a phone call from [Quon]. He says, ‘Don’t sign with Def Jam.’ I said, ‘Fuck that, I’m signing. This is my dream, this is the greatest thing ever.’ Because they were ready to buy my contract from Ichiban. He said, ‘Don’t sign. I’m on my way to New York and I’ll give you millions and millions of reasons why you shouldn’t sign.’ I was like, ‘OK, I’m going to hold off.’ I understood that one.”

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“All right stop, collaborate, and listen.” It’s one of the most ingratiatingly bizarre opening lines of all time. I wouldn’t necessarily rate “Ice Ice Baby” alongside rarefied icebreakers like “I break bread, ribs, and hundred-dollar bills” or even “The government tried to ban me from the dark web,” but it remains as seared into memory as my first phone number. Nothing about it really makes sense. Are you being invited to collaborate with the VIP Posse? Are these the instructions to a junior high group science project? Pay no mind. Step into the cinematic free-for-all of “Ice Ice Baby,” a flamboyant exercise in flamingo-pink color schemes and Lamborghini dreams.

Ice cruises A1A in South Beach looking like a Miami Hurricanes fixer, moussed hair blowing in the wind, steady as a rampart. His cheekbones are scythe sharp and James Dean sunken, but the zigzag lines razored into his hair are strictly Dallas. In the next shot, he and the crew hit a synchronized running man in a warehouse, dressed like the world’s most dangerous valet attendants. A sultry woman wearing a little more than a bikini takes a break from eating an ice cream cone to spray-paint “Ice” in lavender.

Laugh at what it became, but “Ice Ice Baby” remains a perfect debut rap single. It’s an ingenious exercise of self-branding almost up there with Method Man calling his first single “Method Man.” Half the battle is getting people to remember you. Vanilla Ice has only one song that your average music fan can name, but nearly every music fan can name that one song. That is power. That is waxing chumps like a candle. The hook might as well be a subliminal brainwashing koan. Earthquake’s voice whispering “Ice Ice Baby … Vanilla Ice Ice Baby … Too cold” and hitting the boombox in the back of your hippocampus.

He’s certainly no Guru, but the lyrics are nonsensical and memorable in the same way that “lemonade was a popular drink and it still is” is. Ice is back with a new invention, but this is his first major song. He’s flowing like a harpoon, glowing in the dark, going crazy when he hears a cymbal. There are a sideways diss at Kid N’ Play, rhymes sold by the gram, and a 12-bar mini-story rap about clutching a 9 millimeter on Collins Avenue, getting into a shootout with dope dealers, and trying to escape through the clotted traffic. The cops pass him and his friend D-Shay by to confront the dope fiends. Of course they do. Ice looks like Ice. This is part of the problem. But then the bass line from Queen’s John Deacon and David Bowie does its “ding-ding-ding diddle ing-ding,” the sleigh bells shake, and all is temporarily forgiven.

At 8 years old, I considered “Ice Ice Baby” one of the best rap songs ever made. To be fair, it had ferocious competition from “Bust a Move,” “U Can’t Touch This,” “The Humpty Dance,” “Pump Up the Jam,” “Groove Is in the Heart,” and “Parents Just Don’t Understand.” This was third grade; I was far too young and absent an older sibling to be into Public Enemy and N.W.A. There was no understanding of what was pop and what was considered “real hip-hop.” I vaguely intuited that Shock G and Humpty Hump might be the same person after all, but I had no clue what either of them were doing in the Burger King bathroom.

There is a tendency to disregard music loved in childhood as profoundly uncool—at least prior to TikTok, where now even nominally cool things exist in an amniotic state of theatrical sadness. But the ideal judge of a song’s quality is actually that blank-slate condition. There are no expectations, biases, or anything deeper than the dim awareness of “I like this.” I’d never heard of Queen or David Bowie. Had someone patiently explained that, well, actually, the “Under Pressure” loop is rather obvious, and Ice’s flow is rudimentary and stilted compared to stylistically inventive MCs like Big Daddy Kane, Rakim, and Kool G Rap, my eyes would’ve glazed over. How were you supposed to lip-synch to them?

I wasn’t the only one. In 2018, Nipsey Hussle was asked about “Ice Ice Baby” and answered, “I can’t lie to you. I liked that song when I was little. I can’t hate on Vanilla Ice. How you going to hate on ‘Ice Ice Baby’? That’s a classic.” And Houston rapper Riff Raff, once the subject of a Hot 97 debate about whether he was the “next Vanilla Ice,” has repeatedly expressed his admiration for his fellow Texan: “Vanilla Ice is cool as shit. … Why would you talk down to someone who sold 11 million copies of their first album?”

The wave kept cresting. The most influential hip-hop station on the West Coast, the Bay Area’s KMEL, played “Ice Ice Baby” almost every hour. Every other station soon followed, save for Dallas’s KNON-FM, which scorned him. In a rush to capitalize on the hysteria, SBK repackaged Hooked with a new name, To the Extreme, adding three new cuts and some interludes. By releasing “Ice Ice Baby” on 7-inch, 12-inch, cassingle, and CD single, the label cannily maximized its sales potential. In October 1990, both single and album cracked the top 10. At the top of the next month, “Ice Ice Baby” became the first rap song to reach no. 1 on the Billboard Hot 100. Only a week later, To the Extreme supplanted MC Hammer’s Please Hammer Don’t Hurt ’Em at the top of the album charts. In response, SBK reportedly stopped pressing up the single to force consumers to buy the full-length. The gambit worked: To the Extreme spent the next four months at no. 1.

Koppelman, the archetypal old-school, cigar-chomping mogul, estimated that Ice created $100 million worth of business in four months, claiming that “Vanilla Ice isn’t merely a musical phenomenon or a rap phenomenon, he’s an economic phenomenon.”

III. Will It Ever Stop? Yo, I Don’t Know

A newspaper article triggered the eventual crash. Ice had only one week to savor his reign as the world’s most popular artist. This time, the knives didn’t come from a devil-worshiping posse, but a November front-page story in the Dallas Morning News that alleged significant falsehoods in his press biography. Ice’s one-sheet claimed that he was a Team Honda national motocross champion with thousands of trophies, and had attended Palmetto High School alongside Luther Campbell of 2 Live Crew. His Dallas origins were completely omitted. The wider coverage seized on even minor discrepancies like his mother teaching music at a small college and not a major university. Most damningly, they uncovered his government name, Robert Van Winkle.

In retrospect, the scandal was laughably trifling. At the time, Ice admitted to “bending the truth,” but swore that he was briefly enrolled at Palmetto High, one of many schools that he barely attended. He was a Texas motocross champion, but on a smaller regional circuit. For all the derision he received for attending middle-class R.L. Turner High in suburban Dallas, there was barely any digging into his Southside roots. It was an elaborate game of gotcha. Bob Dylan pulled the same move, even writing in his autobiography that he figured that the press was something “you lied to,” but he was Bob Dylan so people considered it part of the enigma. But as Ice rocketed to stardom, the Milli Vanilli lip-synching scandal unfolded in the background. It was a time of intense press scrutiny and obsession with authenticity, magnified by Ice being the first solo white rap star in a Black art form.

To Ice, there were never any lies, per se. He maintains the press bio was concocted without his permission; the rest were purposeful omissions to protect his family’s identity.

“When the press showed up at my door, I got scared,” Ice says. “You’ve got to understand, here’s a kid who had seen people get murdered at 16 years old, shot right in front of me, with bullet holes in their face, and I vomited. I saw shit I shouldn’t see. I’m not going to go out like, ‘Here’s my name, here’s my address. Come on over and kill me.’ Fame scares the fuck out of somebody. When you’ve seen what I’ve seen in the streets, you always elude people. You have to stay safe and protected.”

The media lampooned his claim that he came from “the streets,” but Ice countered with the Rakim line that it ain’t where you’re from, it’s where you’re at. Moreover, becoming a rapper in the mid-to-late ’80s was nothing like it is today.

“When I said that I was from the streets, I meant that that was where I learned to rap,” Ice says. “It wasn’t anywhere else that anybody could learn it. We didn’t have the fucking internet. We didn’t even have computers.”

The narrative had irrevocably shifted. Rather than focus on the details of his rise, every newspaper and magazine picked apart the inaccuracies. The controversies mounted after he dropped off Hammer’s tour, not long after To the Extreme bumped the Oakland minister from the top spot. Ice joked that finally someone had “touched [Hammer].” It didn’t help that the SBK marketing team copied the latter’s runaway success and festooned their young superstar in Hammer pants, sequined jumpsuits, and military suits. As jingoism ran high during the Gulf War, they costumed Ice in an American flag motif. It was very corny. He says that toward the end of his stint on the tour, his merch began outselling Hammer and a friendly rivalry broke out, which briefly turned acrimonious as the media baited them into taking shots at each other.

Then there was the “Under Pressure” sample. According to Earthquake, Queen, David Bowie, and their publishers took 85 percent of the royalties. Clueless journalists lambasted Ice for stealing the riff rather than practicing hip-hop tradition. To be fair, Ice did himself no favors when he gave interviews admitting to the sample, but goofily splitting hairs between the “ding ding ding” of the two songs’ bass lines.

To hip-hop devotees, the brazen sample flip was the first of several acts of war. The genre started with outright heists of Chic’s “Good Times” and Liquid Liquid’s “The Cavern,” but Ice dropped right as the Bomb Squad, Prince Paul, and the Dust Brothers were creating psychedelic sample mosaics that felt like the next advancement of Phil Spector’s Wall of Sound. By 1997, Puffy and Mase would rip off “Let’s Dance” with a video of them getting jiggy in the middle of the Sahara with what appeared to be an Algerian militia. It elicited a modest furor, but the mad rappers were slowly silenced. What Ice was crucified for practically eventually became a hip-hop rite of passage.

Back in late 1990, the 23-year-old became the pale face of hip-hop apostasy, attracting oblivious Karens and Brads at a startling clip.

“I was mentioning eight balls of cocaine, 9-millimeter guns, a 12-gauge shotgun, and prostitutes. You can’t paint this picture to a 9-year-old. So how did they clean it up? Use the image, let ’em focus on the beat and the dancing—it worked,” Ice says. “I wasn’t targeted to be a role model; I was never put out as an artificial boy-band thing to fit this new audience that I was catering to now. All of a sudden, it went from Black clubs that I thought I’d been in and would be in forever to stadiums with white people.”

Robert Christgau, then the reigning dean of critics, eviscerated him for being somehow “blander than Hammer.” The barrage of criticism felt intentionally ruthless; To the Extreme might be far from a classic, but “Ice Is Workin’ It” is a surprisingly muscular display of lyrical bluster, à la LL Cool J. The pair of Khayree songs are funky party tracks that admirably convey why KMEL booked Vanilla Ice to headline its New Year’s Eve 1991 concert. There are certainly embarrassing moments, like the sappy ballad “I Love You” or “Rasta Man,” which seems like the covert blueprint for Lonely Island’s “Ras Trent.” But even absent “Ice Ice Baby,” it’s essentially a replacement-level 1990 rap album, no worse than anything Kwamé put out.

The Source, the bible of hip-hop, ran a one-page diatribe by Dan Charnas with the headline “Vanilla Ice: Our Worst Nightmare?” He envisioned the “nightmare become reality” where the American mass media pigeonholes hip-hop as the totality of Hammer, Ice, and Young MC, where true innovators would get whitewashed by derivative pop opportunists. Nonetheless, Charnas incisively noted that Ice was similar to what MC Serch of 3rd Bass might’ve been like had he grown up in the South.

“I remembered watching [Hammer’s] ‘U Can’t Touch This’ video and being really angry. What is this shit? It’s horrible. He was definitely a good dancer, but this is the worst song I’ve ever heard. The Rick James sample was so obvious,” says Jonathan Shecter, the cofounder of The Source and its editor-in-chief from 1988 to 1996. “We’d already started writing negative things about Hammer, then out of nowhere came ‘Ice Ice Baby,’ this even more offensive song. The sample was even more obvious, and I didn’t like his rapping either. It became the biggest song in the world and now we had another enemy. Now, all of our anger was directed at him.”

Ironically, Shecter had been one-half of B.M.O.C., the duo of white rappers who first sampled “Play That Funky Music.” The entire staff of his publication—Black, white, Latino, and Asian—all shared a mutual loathing of Hammer and Ice. Only later did Schecter reconcile the vampiric nature of the music industry. No matter how many indignant essays were written, record executives would continue their desperate search for an MC Hammer or Vanilla Ice of their own.

Every label tried to sign a white rapper. In a reminder that life is totally arbitrary and we are all susceptible to confirmation bias, Public Enemy and the Bomb Squad put on a group of white kids called Young Black Teenagers. Competent but unoriginal, YBT rapped about Kelly from Married With Children and cringingly titled a song “Daddy Kalled Me Niga Cause I Likeded to Rhyme.” This interview may as well be the foundational text for Rachel Dolezal, but because of their connections, they received a pass. Eazy E tried and failed twice with Tairrie B and Blood of Abraham. Jive hoped that Kid Rock would give them an “Ice Ice Baby,” but instead his Grits Sandwiches for Breakfast bricked despite production from Too Short and D-Nice of Boogie Down Productions. The only “success” was Marky Mark in 1991, who racked up a no. 1 record for a hip-house track produced by a member of New Kids on the Block while somehow receiving a fraction of the censure as Ice.

“My image would’ve been different if I’d signed to Def Jam, but it’s hard to speculate how the record sales would have been impacted,” Ice says. “A lot of people probably could see me being more respected with a crew like Public Enemy, instead of being all alone and being put into the pop world. It probably would have happened on its own anyway though. ‘Ice Ice Baby’ was magical; it had fairy dust all over it.”

For all the nuclear attacks, hip-hop would’ve gone mainstream with or without Vanilla Ice. In many respects, Kid N’ Play established a template for Hammer and Ice’s brand of poppy dance rap, but because they were from the Bronx and Queens, purists (accurately) recognized them as the latest evolution of the four elements—kid-friendly but still reverent of tradition. The same month that To the Extreme dropped, NBC premiered The Fresh Prince of Bel-Air and Kid N’ Play, a Saturday-morning program that turned the latter into literal cartoons. Yet when artists from the Bay and Dallas/Miami did it, their commercialization was considered hip-hop’s death knell.

In reality, the genre had been steadily crossing over since 1986, when Run-DMC covered Aerosmith’s “Walk This Way” and the Beastie Boys tapped into a fraternity crowd that needed white rappers talking about beer, burgers, and girls to make them care. In 1989, the Grammys introduced the Best Rap Performance category, giving the first award to DJ Jazzy Jeff and the Fresh Prince. In that same year, Young MC, Tone Loc, and Biz Markie all cracked the upper reaches of the Billboard Hot 100. Just before Hammer and Ice’s 1990 takeover, Bell Biv DeVoe and Salt-N-Pepa became pop-rap sensations. Ice certainly wasn’t the first nor would he be the last; he just happened to be the largest target.

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You could almost see the gears turning in Keenen Ivory Wayans’s head. In January 1991, the In Living Color creator was tasked with introducing Vanilla Ice’s performance of “Ice Ice Baby” at the American Music Awards. Dressed like Captain America meets Aladdin, Ice eventually won the award for Favorite New Pop/Rock Artist. Flanked by Quon and the VIP Posse, Ice gave an abbreviated but memorable speech that concluded with his saying “to the people who try to hold me down and talk bad about me, kiss my white butt.”

“I was getting hate everywhere. I was like, ‘I’m going to show y’all. Here it is, in your face. Eat a dick. Fuck you,’” Ice says. “It was wrong and I regret it; I was stupid, young, and dumb. Shit hit me from left, it hit me from right, from above and from under. I wasn’t coached on what to say. In hindsight, I should’ve just thanked my mom.”

It’s hard to blame him much. He was 23 and secure in the belief that every artist has when they’re on top of the world: This will continue forever. Despite the searing criticism, things still looked rosy. He had just filmed the iconic “Ninja Rap” scene from Teenage Mutant Ninja Turtles 2: Secret of the Ooze and Madonna had popped into his dressing room at Madison Square Garden to give him her phone number. They became a couple after he visited her in Indiana on the set of A League of Their Own, culminating in his appearance in her Sex book.

Photo by Bill Nation/Sygma via Getty Images

No one could’ve defended against what came next. On Sunday, February 10, 1991, just 12 days after Wayans watched Ice perform at the AMA’s, Jim Carrey parodied him on In Living Color. “White White Baby” is a massacre. It’s not technically a diss song, but if it were, it’d be up there with “Who Shot Ya,” “The Bridge Is Over,” “Hit ’Em Up,” and “Takeover”/“Ether.” It’s difficult to convey the magnitude of the Fox sketch show in 1991. It had been on the air for only 10 months, but it had become the hip-hop generation’s analogue to Saturday Night Live in the late ’70s. We now recognize Carrey as a brilliant satirist, imitator, and actor who was on the verge of becoming Hollywood’s most bankable comic. But at the time, all anyone knew was that Fire Marshal Bill had just set Vanilla Ice up in flames.

If the previous fusillades were often academic and easily dismissed, “White White Baby” was the shit that made your soul burn slow. Carrey pulls off the look perfectly: the cuts in his scalp, the dazzling preposterousness of the emperor’s new pajamas, the all-Black backing dancers with the “marketable” face up front. Had it been anyone else other than the future Ace Ventura, Ice might’ve been spared, but Carrey was already a master. The gesticulations and flailing dance moves were amplified just enough to make you question why you liked Ice in the first place. It was both slapstick and skull-crushing: As he rapped “Let’s kick it,” Carrey sent a single shoe into the rafters and chased after it like an outfielder losing a fly ball in the sun. His Ice is an empty mannequin, a brainless puppet foisted into the spotlight solely because of his skin color—rap’s Manchurian candidate, backed by the dark machinations of industry to exploit a rich cultural tradition.

With all savage parody, there is enough truth for it to stick. With all good comedy, it’s fucking absurd. Carrey does a Three Stooges routine while pumping his arms and skittering backward on one leg. He pelvic-thrusts, turkey-necks, sticks his tongue out, and does the “I’m a little teapot short and stout.” The dancers do a call-and-response mocking his real name, and Carrey says nothing rhymes with Van Winkle.

With pitch-perfect mannerism and vocal tone, Carrey spits, “I’m white and I’m capitalizing / On a trend that’s currently rising.”

Before ultimately leaving in disgust, the dancers chant: “When you gonna stop?”

“Maybe never,” Carrey responds. “I become richer with every endeavor. … I’m living large and my bank is stupid / Because I just listen to real rap and dupe it.”

Ice was arraigned as the latest in a long line of white appropriators, from Bix Beiderbecke to Elvis to Led Zeppelin. If he’d received private support from some of rap’s most respected figures, he was an unguarded mark in the public eye. Dallas wasn’t about to defend him because he didn’t represent it, and even if it had, unless Michael Irvin stepped forward to say that he’d seen Ice kill brains like poisonous mushrooms, no one would’ve cared. Nearly a decade later, the Interscope brain trust knew to pair Eminem with Dre to ensure his street credibility and avoid another Vanilla Ice meltdown. But Ice had emerged at the apex of the conscious rap era, unaffiliated and dressed like an opulent Nordic dictator. It was open season.

The fait accompli occurred just two days later. Invited on The Arsenio Hall Show, Ice walked blithely into the lion’s den. This was peak Arsenio, where the Dog Pound was howling and the best rappers and entertainers appeared nightly. The same year that they turned over the program to Prince one night for the best hour of music television ever aired. Someone should’ve warned Ice.

It remains a brutal interview to watch. You can practically see Ice’s career leave his body. There is none of the jocular banter of late-night programs. From the start, Hall is antagonistic and aiming for the jugular. Dressed in a bedazzled green-and-white proto Power Ranger suit, Ice is immediately greeted by Flava Flav. A scowling Hall hammers him on the American Music Awards gaffe, his “white rapper revenge oppression,” the mistruths in his biography.

Ice’s rebuttals are reasonable, but he’s defensive and rattled. It doesn’t help much that his hair is sculpted and blow dried, the cuts in his eyebrow delicately shaved. Had Ice shown up looking like he had on the cover of Hooked, it might’ve gone differently, but he was too deep into his public persona.

For all his missteps, Ice never wavered from acknowledging his creative debt to a Black art form. He gave a lot of foolish quotes at the time, but his commitment to the culture was deep and genuine, even if it got lost in the mass-market translation. As ridiculous as his Ice by Ice book was, he shouted out his love of Rakim, the Geto Boys, Big Daddy Kane, N.W.A, and Audio Two—singling them out as brilliant artists who deserved more love from the mainstream music world.

But Arsenio wouldn’t concede an inch. He’d later explain that he’d felt like he’d been used and misled by biographical information that Ice’s team had given him. He was “pissed.” When Ice tried to point out his friendship with Flava Flav, Arsenio spat back, “Is that why you brought him out, to show that you have a Black supporter?”

There was no point to explaining the City Lights years or the fact that Chuck D had tried to sign him. After all, this is what mass culture does: It flattens and removes the arcane but relevant details. The people want the shiny suit until they don’t want it anymore. Then there’s always a next model to replace it.

As his world was collapsing, Ice says that a young 2Pac was one of the people who gave him the strength to keep enduring. This was a young Pac, fresh off “Same Song” with Digital Underground and about to begin recording his debut, 2Pacalypse Now.

“We’d played some early shows together with Digital Underground and let me tell you, 2Pac was one of the biggest Vanilla Ice supporters you ever met,” Ice says. “He gave me great advice: Keep your head up, don’t let no haters fucking keep you down, keep doing your thing, and don’t focus them people ain’t paying for your bills. You know who is? The ones that’re buying it. Focus on them.”

According to lore and VH1, 2Pac’s future label boss, Suge Knight, paid a visit to Ice’s room at the Bel Age Hotel the same night as the Arsenio Hall taping. The story famously holds that the former University of Nevada defensive end dangled Ice from a balcony in order to secure songwriting points off “Ice Ice Baby.” In Knight’s version, Ice had stolen the lyrics from Mario Johnson, Earthquake’s former collaborator. In Ice’s version, Knight extorted him into signing away millions of royalty dollars, which became part of the seed money for Death Row.

As with all things pertaining to Vanilla Ice, the absolute truth is impossible to ascertain, but the stories are relentlessly entertaining. In Earthquake’s reminiscence, Knight approached Quon on the set of Arsenio demanding money from “Ice Ice Baby,” but the manager demurred. Later that evening, Knight and his hulking bodyguards found their way into Ice’s suite for an impromptu business meeting.

“Every time Mario [Johnson] said something, Ice would interrupt him and call him a liar,” Earthquake says. “Suge said, ‘Ice, when you had the floor, no one interrupted you.’ Ice interrupted two more times. After the third time, he said, ‘Ice, I’ma ask you more time or I’ma throw your ass off the balcony.’”

Earthquake says that he never saw Ice pen the lyrics to “Ice Ice Baby”; in his last conversation with Johnson—who Suge would soon rename “Chocolate”—the rapper emphatically refused to write anything for Ice.

In Ice’s rendition of the Suge confrontation, Johnson was a minor acquaintance whom he’d given a few rides home after the club. Suddenly, “Ice Ice Baby” became the biggest song in the world. Ice had temporarily moved to L.A. and met Suge Knight, who started suspiciously materializing wherever he went, dressed in black suits and shades like a Mafia don. Finally, he appeared inside his luxury hotel room.

Ice vehemently swore that he wrote every bar to “Ice Ice Baby.” He says that Suge politely asked him to step out on the balcony for a conversation. His bodyguards came in armed, but peaceful. No one was looking for trouble, but they wouldn’t go out of their way to avoid it either. They told Earthquake to sit down and shut up, and everything would be cool. The same went for Ice’s bodyguards. Out on the balcony, Suge began explaining that he would take some points off the record; at this point, Ice says that he didn’t even know what that meant.

“He says, ‘Ice, listen, man. Here in L.A., it’s rough. There’s a lot of gangs.’ He explains a lot to me that I already knew; rap music had always been gangster,” Ice says. “I asked, ‘What am I paying for?’ He says, ‘Protection … because of all these gangs. We’re going to be looking after you now. You’re in with a very tight clique.’ He said so many rappers and musicians that you wouldn’t even think pay Suge Knight.”

It was the proverbial offer that he couldn’t refuse. Ice signed away two points on the spot, technically to Johnson, who Ice says was brought back into the room freshly bloodied and bruised.

“I was like, ‘What the fuck is this? Damn.’ It just went from being peaceful and shit to crazy,” Ice says. “Suge said, ‘This is how we’re going to get our points right there [pointing at Johnson].’ So, they basically took those points and put [Johnson] in the place where he wasn’t. He didn’t help me write anything.”

Things only grew worse. Rather than get him back in the studio to follow up the smash that had been recorded years before, SBK tried to cash in with the extremely bad Extremely Live—a live album with a few new songs, including “Rollin in My 5.0,” which tried to replicate “Ice Ice Baby” but this time with a sample of Steve Miller’s “Fly Like an Eagle.” It was critically loathed and the singles failed to chart; the album peaked at no. 30 and quickly disappeared into record store bargain bin eternity.

By the summer of 1991, Marky Mark had replaced Ice as pop’s flavor-of-the-month white rapper. In a bulldozing attack, 3rd Bass dissed Ice with “Pop Goes the Weasel.” The song was good, but the appropriations committed by the white rappers from Queens and Long Island were no different from those perpetrated by Ice. They jacked a straightforward pop hit (Peter Gabriel’s “Sledgehammer”), used Black people and the Watts Towers (?!) as props to score authenticity points, and presented themselves as white saviors attempting to preserve hip-hop’s cultural purity. The Source pointed out the deceptive similarities between Ice and MC Serch, but the other rapper in the group, Pete Nice, had an English degree from an Ivy League school. Ice was a high school dropout from a broken home—not to mention that he had dramatically better dance moves than the bespectacled Serch.

But because they were from New York, signed to Def Jam, and had recruited punk rock legend Henry Rollins to play Ice in the video, 3rd Bass was hailed as a refreshing change from Ice’s “same old thieving.” Between In Living Color, Arsenio, and 3rd Bass, I completely bought in too. Ice suddenly became played out and corny. A Tribe Called Quest’s Low End Theory dropped that September. On the “Scenario” remix that came out a few months later, Phife sneered “Vanilla Ice platinum? That shit’s ridiculous.”

The Ice Age formally ended that October with the release of Cool As Ice. Financed by SBK at the apogee of his success, the film was conceived as a modern cross between The Wild One and Jailhouse Rock. Though it’s since become a sort of camp classic, it received atrocious reviews and grossed just $1.2 million on a $6 million budget. The soundtrack album flopped, and the film was nominated for seven Golden Raspberry Awards. Ice won the Razzie for “Worst New Star”; he did not show up to accept the trophy.

IV. Word to Your Mother

If anyone disproves the F. Scott Fitzgerald cliché about second acts in American life, it’s Vanilla Ice. But what’s overlooked about that adage is the idea that while one’s life can splinter in new directions and even regenerate to a degree, there remains the lingering memory of that first pristine wave of success. This is a nation perpetually in thrall to the new, simultaneously sentimental and suspicious of age. No matter how many times Ice has attempted to rebrand or redefine himself, there is the understanding that it could go only so far. “Ice Ice Baby” was too big, too era-defining, the song you chase forever until you eventually learn to let go.

“It was beyond wildfire, beyond a tsunami. Just unbelievable success, so fast, and so incredibly impactful—to the point where we look back 30 years later and ‘Ice Ice Baby’ has become an anthem that actually defines the ’90s,” Ice says. “All you have to do is play ‘Ice Ice Baby’ and you’ll remember everything you were wearing, who you were dating, how cheesy and corny we were. The ’90s just had that attitude.”

Photo by Matthew Eisman/Getty Images

The more accurate Fitzgeraldian aphorism to describe Ice is “Vitality shows in not only the ability to persist but the ability to start over.” Anyone with a passing familiarity with pop culture has witnessed at least a half-dozen versions of Ice. After vanishing in late ’91, he retreated to a mansion on Star Island to pursue a decorated motocross and Jet Ski career (he was ranked no. 6 in the world in the latter at one point). Upon his ’94 reemergence, he tried to adapt to the times by going hardcore, sporting dreadlocks and rapping about weed smoking like an excited teenager who had just hit his first bong. After it failed, he nearly overdosed, which led him toward spirituality, therapy, marriage, and a grunge band. There was the nu-metal phase when he collaborated with one of Korn’s producers and another phase at the beginning of the millennium when he appeared on any reality show that would take him. Eventually, he landed on VH1’s The Surreal Life, where Tammy Faye Bakker offered the most valuable advice that anyone had given him since 2Pac: “Honey, you are who you are because of who you were. Embrace it.”

There were brushes with the law: a 2008 arrest after his wife said he kicked and hit her (the charges were later dropped after she recanted). He copped to a plea deal in 2015 related to charges of residential burglary and grand theft after police say he took furniture, a pool heater, and bicycles from a Florida home that he presumed was vacant. He became a Juggalo and released an album on ICP’s label, starred in an Adam Sandler movie, played Captain Hook in a British production of Peter Pan, and nearly was involved in a Fourth of July concert in Texas that was called off because of COVID-19 concerns. This is all in addition to the decade-long run of The Vanilla Ice Project.

Most recently, Dave Franco announced an Ice biopic in the vein of The Disaster Artist. The logline for To the Extreme reads: “From a high school dropout selling cars in Dallas to having the first hip-hop single to top the Billboard charts … a young Vanilla Ice struggles with stardom, extortion attempts and selling out as he makes music history.”

In the three decades since the album’s release, it has become difficult to see the world in which it all emerged. The questions of cultural appropriation and artistic integrity continue to be paramount to the modern conversation, but it is almost impossible to imagine a landscape where a few negative articles, a comedy sketch, and a rough appearance on a syndicated late-night show could cause the biggest artist on earth to completely implode. The fear of Ice was that it would hasten a world in which the urgent salvos of Public Enemy and N.W.A would never reach white Middle American households. But both are deservedly enshrined in the Rock & Roll Hall of Fame, and the latter had a biopic that grossed more than $200 million and was nominated for an Academy Award.

After Vanilla Ice and Marky Mark left the limelight, another solo white rapper wouldn’t become famous until Eminem eight years later. And after that, it would be over a decade before Macklemore raised all the same troubling questions that had first been asked during the presidency of the elder George Bush. Hip-hop has been so thoroughly co-opted and embedded into the mainstream of pop existence that rappers, many of them white, can pack arenas without remotely intersecting with the street world. The question of selling out is so obsolete that Travis Scott—who never met a beat, ad-lib, or nickname that he couldn’t steal—can do a nihilistically shameless cross-promotional deal with McDonald’s. And rather than catch flak for partnering with a soulless corporate behemoth, millions of teenagers treat his pseudo Happy Meal like the holy grail.

If Vanilla Ice were to debut today, he might be something like G-Eazy, a well-meaning and technically adequate rapper acknowledging his cultural debt. After all, the Bay Area artist got his start selling post-hyphy music on the streets of Berkeley and Oakland before cleaning up his image to look like a leather-jacketed ’50s black-and-white matinee idol.

The more accurate comparison might be Post Malone, a fellow Dallas native who has been condemned for borrowing hip-hop tropes without paying the proper respect to the art form. In a fitting twist, Malone records for Republic, the label founded and run by Monte Lipman, the original A&R who discovered Ice in 1990. But whereas Ice was felled by the ceaseless avalanche of criticism and scorn, Malone’s star has only ascended in spite of, or maybe even because of, it. When I wrote a diatribe against his staggering creative emptiness, woeful theft, and insistence on treating hip-hop like a Halloween costume, I received death threats and was the subject of multiple articles questioning my objectivity. We have been in the “too big to fail” era for far too long, and it extends to all walks of life, except maybe the country itself.

As for Vanilla Ice, it would be comforting if we could look back and believe that all the hatred was meant for something, rather than as an ideological Alamo for gatekeepers desperate to stop an inexorable annexation. He survived, made millions of dollars, the story ends well. But it is difficult to remember his rise and fall as anything but a senseless casualty, for important causes that no one can quite remember.

Jeff Weiss is the founder and editor of POW. His work has appeared in The Washington Post, the Los Angeles Times, and GQ.