In The Number Ones, I’m reviewing every single #1 single in the history of the Billboard Hot 100, starting with the chart’s beginning, in 1958, and working my way up into the present.
It happened. It finally happened. A rap song reached #1 on the Billboard Hot 100. This was a long time coming. Hip-hop, as a form of music, had its semi-official beginning in 1973, when Kool Herc, the Jamaican-born teenage DJ, played records at a back-to-school party in the rec room of his Bronx apartment building, cutting between the percussive breaks of funk singles and accidentally birthing a whole genre. For years, rap was just live party music, with MCs chattering over the breaks that their DJs put together. Then, in 1979, the Sugarhill Gang, a trio of New Jersey kids assembled by the indie-label boss Sylvia Robinson, made “Rapper’s Delight,” a 15-minute record in which they rapped euphoric rhymes, many of them stolen, over the groove from Chic’s disco hit “Good Times.” “Rapper’s Delight” went top-10 in a bunch of countries and peaked at #36 on the Hot 100, and rap music has been a part of pop ever since.
After “Rapper’s Delight,” it took 11 years for a rap single to reach the top of the Billboard Hot 100. There are a lot of reasons for this. Rap was essentially an underground genre, and it developed a reputation for being loud and disreputable and off-putting, a fad to be mocked. In the second half of the ’80s, rap songs would break through into the top 10 here and there, but the songs that charted highest tended to be the ones that referred back to fondly-remembered older music. In 1986, Run-DMC became the first rap group to reach the top 10 when they teamed up with Aerosmith’s Steven Tyler and Joe Perry for a half-rapped version of the Aerosmith oldie “Walk This Way.” The Run-DMC version of “Walk This Way” peaked at #4, and it helped bring about a grand comeback for Aerosmith. (The Run-DMC “Walk This Way” is a 5. Aerosmith will eventually appear in this column.)
As the ’80s drew to a close, rap records reached the top 10 more and more often. In 1989, the deep-voiced LA rapper Tone Lōc made it as high as #2 with “Wild Thing,” a song built around a sample of Van Halen’s “Jamie’s Cryin’.” (“Wild Thing” is an 8.) A year later, MC Hammer definitely should’ve gone to #1 with his ridiculously huge smash “U Can’t Touch This,” which anchored Please Hammer Don’t Hurt ‘Em, the year’s biggest-selling album. But Hammer’s label didn’t sell cassingle copies of “U Can’t Touch This,” pushing the public to buy the album instead of the single. As a result, “U Can’t Touch This” peaked at #8. (It’s an 8.)
“Wild Thing” and “U Can’t Touch This” didn’t top the Hot 100, but rap music was quickly becoming more and more of a presence in the songs that did. The first rap-adjacent single to reach #1 was Blondie’s “Rapture,” way back in 1981. (I’ve seen people call “Rapture” the first rap chart-topper, but you’d have to be stretching definitions pretty far to call that a rap song.) In 1989 and 1990, various teen-pop and dance-pop stars borrowed liberally from rap. The New Kids On The Block reached #1 with the quasi-rap hit “Hangin’ Tough.” Milli Vanilli — or the studio musicians who recorded as Milli Vanilli — spent almost as much time rapping as singing. Bobby Brown rapped a guest verse on Glenn Medeiros’ “She Ain’t Worth It.” A cartoon cat rapped on Paula Abdul’s “Opposites Attract.”
Finally, in the fall of 1990, a straight-up rap song climbed the chart summit and earned itself a spot in history. It was not a coincidence that this triumphant single came from a clueless and absurdly good-looking young white guy. It was also not a coincidence that the song in question was built on a hyper-obvious sample of a rock-radio standby. By the time this white kid reached #1, rap music had already matured into its own diverse, divisive, often-brilliant musical culture, and that culture was overwhelmingly Black. The people involved in that culture were not overjoyed at the sight of this white kid suddenly coming along and taking his bubble-rap hit to the top of the pop charts, and that triumph had plenty of unpredictable consequences in the decades to come. But someone had to be the first rapper with a #1 hit, and that someone turned out to be Vanilla Ice.
Robert Van Winkle was born in Dallas, the son of a music-teacher mother and an absent father. (When Van Winkle was born, the #1 song in America was Lulu’s “To Sir With Love.”) Eventually, Van Winkle’s mother married an Ecuadorian immigrant who worked at a car dealership, and Van Winkle grew up in between suburban Dallas and suburban Miami. As a kid, Van Winkle fell in love with hip-hop because of Breakin’, a 1984 movie that was arguably one of the first big corporate attempts to cash in on hip-hop culture. Van Winkle started rapping and breakdancing for spare change from onlookers in Dallas malls, and for obvious reasons, he started calling himself MC Vanilla. That name eventually evolved into Vanilla Ice.
In the late ’80s, a teenage Vanilla Ice was a regular at City Lights, a Dallas nightclub where he was usually the only white face in the crowd. One night, on a dare from friends, a slightly drunk Vanilla entered a City Lights talent competition, and the mere novelty of this dancing white boy was enough to win over the crowd. Tommy Quon, the owner of City Lights, took notice, and Vanilla Ice became a house act at the club, opening for touring artists like 2 Live Crew, Paula Abdul, and MC Hammer. I once read an interview where Geto Boys member Willie D claimed that he tried to convince Rap-A-Lot Records, the historically hard Houston label that released the Geto Boys’ records, to sign Ice. One night, Ice also opened for Public Enemy, and apparently Chuck D was so impressed that he tried to help Ice sign to Def Jam. While watching Vanilla Ice perform, Chuck reportedly told somebody, “I can make a lot of money off that white boy.” (Last year, my friend Jeff Weiss published a great Ringer story about the whole Vanilla Ice origin story. It’s fascinating stuff.)
Tommy Quon became Vanilla Ice’s manager, and he teamed Ice up with DJ Earthquake, the club’s resident record-spinner. Ice and Earthquake started making tracks together, sampling recognizable hits and not trying to hide those samples, the way that other rap producers would do. Eventually, Quon got Vanilla signed to Ichiban Records, a small indie in Atlanta, and Ichiban released Hooked, Ice’s debut album, in 1989. The lead single from the album was “Play That Funky Music,” built on a truly obvious sample of the 1976 Wild Cherry hit of the same title. At first, Ice’s “Play That Funky Music” was a failure, though the song would later reach #4 on the Hot 100. (It’s a 4.)
To promote Hooked and “Play That Funky Music,” Vanilla Ice and Tommy Quon toured through the South, playing clubs and talking to radio DJs. Eventually, one DJ in Georgia started playing “Ice Ice Baby,” the B-side to the “Play That Funky Music” single. “Ice Ice Baby” sampled the spacey, tingling bassline from David Bowie and Queen’s 1981 classic “Under Pressure.” The sample was uncleared, and it would lead to a whole lot of legal trouble in the years ahead. (“Under Pressure” peaked at #29, and I wrote a whole bonus column about that song last year.)
But “Under Pressure” wasn’t the only thing that Vanilla Ice borrowed on “Ice Ice Baby.” the song’s hook came from a chant that Alpha Phi Alpha, a Black fraternity, had been using for years. Spike Lee used that chant in a step-show number from his 1988 musical School Daze. Vanilla Ice got away with that one.
The actual creation of “Ice Ice Baby” is a matter of some dispute. Earthquake has said that he made the beat and that he refused to make Ice a tape of the instrumental. To hear Earthquake tell it, he was angry when he finally heard the track. Ice himself once claimed that he wrote “Ice Ice Baby” at 16 and that he got the Queen sample from his older brother’s record collection. There’s also the matter of Mario “Chocolate” Johnson, a Dallas rapper who briefly worked with Vanilla Ice and who later claimed to have written much of the song. When “Ice Ice Baby” finally came out, Ice was credited as the producer and Earthquake as the co-writer. Mario “Chocolate” Johnson was not credited at all. The clash between Vanilla and Chocolate was still to come.
Whatever its origins, “Ice Ice Baby” stands today as a memorably ridiculous song. The “Under Pressure” sample absolutely works, and it works in the ways that samples are supposed to work. It takes a chunk of “Under Pressure” — that simple little brainworm bassline — and builds around it. The 808s kicks highlight the mysterious spareness of that bassline, and the synths weave subtle melodies under it. The hook, whispered and repetitive, almost sounds like an incantation. And then there are the verses, which are goofy as hell.
On “Ice Ice Baby,” Vanilla Ice himself sounds clumsily enthusiastic, like he’s trying to project cool reserve even though he can barely believe that he’s getting a chance to rap on record. A lot of the word choices on “Ice Ice Baby” are deeply perplexing. I’ve had decades to wonder, and I still have no idea what Ice was thinking on some of those lines: Flow like a harpoon? Killing your brain like a poisonous mushroom? His style’s like a chemical spill, feasible rhymes you can vision and feel? Does he know what all these words mean? And yet those lines stick with you. They are memorable nonsense. Vanilla Ice is also so audibly excited to deliver those lines. Ice keeps his composure when it’s time to get loose, but only barely.
Most of the second verse from “Ice Ice Baby” is a story-song, a tale of Ice out rollin’ in his 5.0 with his ragtop down so his hair can blow. There’s simply no way that hairstyle was moving the tiniest bit, but this is a tall tale, and we should take it as such. This whole yarn takes place in Miami — “my town that created all the bass sound.” (Ice never mentions Dallas, which probably has a better claim on being his town.) In the story, Ice and his DJ D-Shay are out on Beachfront Avenue, packing heat and check out the girls who are wearing less than bikinis. (This detail, in particular, really captured my 10-year-old imagination.) Ice sees that armed cokeheads are out, possibly trying to steal his car. He hears shells falling, and he grabs his gun, but police arrive. For some reason, the cops don’t bother Ice. They confront these dope fiends instead. Presumably, Ice breathes a sigh of relief and goes back to solving problems while D-Shay revolves it.
In other words, the first rap song ever to top the Hot 100 has a whole embedded narrative about a white rapper being happy when the police arrive. In ways that Vanilla Ice presumably never considered, “Ice Ice Baby” is a song about white privilege. The song’s success is also a story about white privilege, though Ice probably had no way of knowing about that. Ice came up in a Black music scene where his race made him the subject of some curiosity but where he had to impress Black listeners. When “Ice Ice Baby” made him famous, things changed. The world started treating Robert Van Winkle like he was a New Kid On The Block.
After “Ice Ice Baby” started to take off on Georgia radio, it spread through the South, and Tommy Quon paid $8,000 to make a video. In the clip, Ice and his friends dance in what appears to be an empty office, with the Dallas skyline looming behind them. For the first 30 seconds of the video, Ice is in shadow, a silhouette dancing with other silhouettes. When he steps into the light and turns out to be a white guy, it’s a dramatic reveal, whether or not that’s what Ice and director Greg Synodis intended. The “Ice Ice Baby” video got play on the Box, the all-request cable network, and on BET’s Rap City, which had just launched in 1989. Soon, the major labels came calling. Ice ended up signing with SBK Records, the newly founded EMI imprint, which was flush with Wilson Phillips money.
SBK rushed “Ice Ice Baby” to the national market, and the label also repackaged Ice’s indie debut Hooked, re-releasing it as To The Extreme. Within a couple of months, “Ice Ice Baby” raced up the Hot 100. Ice arrived in the immediate wake of MC Hammer, who’d built his own regional empire before crossing over to major-label fame but who also emphasized obvious samples and memorably goofy rhymes. Like Hammer, Ice was probably better-known for his dancing than for his rapping. Like Hammer, he was also better at dancing than rapping, which helped the “Ice Ice Baby” video out at MTV. SBK sent Ice out on the road as MC Hammer’s opening act, just as Hammer’s Please Hammer Don’t Hurt ‘Em was in the middle of a months-long run at #1 on the album chart.
When “Ice Ice Baby” rose to #1 in November of 1990, SBK stopped pressing up the single, using the Hammer-style rationale that more people would buy the album if they couldn’t buy the single. It worked. “Ice Ice Baby” only topped the Hot 100 for a week, and it probably would’ve had a longer run at the top if people could’ve kept buying the single. Instead, a week later, To The Extreme knocked Please Hammer Don’t Hurt ‘Em off of the #1 spot on the album charts, where Hammer had reigned since early July. To The Extreme would then spend 12 weeks at #1, and it would sell seven million copies in the US. For a while there, To The Extreme was reportedly selling a hundred thousand copies a day.
Ice dropped off the Hammer tour when To The Extreme bumped Please Hammer, and Ice and Hammer got into a minor and consequence-free public feud shortly thereafter. Ice started headlining arenas himself. He taped a cameo in Teenage Mutant Ninja Turtles II: The Secret Of The Ooze. He starred in Cool As Ice, his own cinematic vehicle. You could buy Vanilla Ice dolls, magazines, board games. He was inescapable. He was a star.
It didn’t last. Ice seemed to have no idea that a backlash was coming, and he carried himself with a beautiful kind of idiot arrogance. But when that backlash arrived, it arrived quickly. SBK had put out a press release with a bunch of made-up details about Ice’s biography, including the claim that he’d gone to high school with 2 Live Crew’s Luther Campbell. The Dallas Morning News published an article about Vanilla Ice’s real local roots and exposed those PR lies. The Source, the reigning rap magazine, ran diatribes against Ice, warning that he could become an Elvis figure for what had been a Black genre. Queen and David Bowie’s lawyers threatened lawsuits over the “Under Pressure” sample, and Ice did himself no favors by claiming in interviews that the two songs were actually totally different.
In February of 1991, shortly after To The Extreme ended its run at #1, Ice went on Arsenio Hall, and Hall did not give Ice the usual softball interview. Instead, Hall called Ice out for his made-up press bio and for profiting on a Black art form, and Ice hemmed and hawed and stuttered and came off, by turns, defensive and ingratiating.
The same night that he went on Arsenio, Ice had a fateful meeting with Marion “Suge” Knight, a former NFL prospect and Bobby Brown bodyguard who was just getting into music management. One of Knight’s clients was Mario “Chocolate” Johnson, the Dallas rapper, who wanted to get paid for the work that he said he’d done on “Ice Ice Baby.” The urban-legend stories about Suge Knight dangling Vanilla Ice off of a Beverly Hills hotel balcony are, by all accounts, false. Instead, it seems more likely that Knight merely made it clear that he could toss Ice off that balcony or do lots of other foul things to him. In any case, Ice ended up signing over a chunk of his publishing to Knight. Ice himself later said that it was worth millions. Some of that money presumably went into the founding of Death Row Records, which launched in 1992. (Suge Knight’s Death Row partner Dr. Dre will eventually appear in this column, and so will Death Row artist 2Pac — who, in Ice’s telling, was always a big supporter.)
In the end, Vanilla Ice would not become an Elvis figure for rap music. If you look at the list of rap songs that have reached #1 in the past 30 years, you’ll get a distorted view of the genre; a surprising number of white rappers have followed Vanilla Ice to #1. Despite that, rap music remained — and remains — a predominantly Black enterprise. In a strange way, Vanilla Ice himself was a part of that. The widespread backlash that followed the success of “Ice Ice Baby” helped change the direction of rap itself, as rappers and fans alike decided that this particular kind of bubblegum rap was corny. Ice, under duress, also probably helped fund the creation of Death Row Records, the label that would popularize a version of rap music that was
There’s a widespread idea that Vanilla Ice ripped off David Bowie and Queen and that this is his greatest musical sin. I don’t agree with that. Sampling is a key part of rap music, and in the years before 1990, virtually nobody cleared their samples. That’s part of the beauty of rap. It’s music made from other music, shards of collective-memory sound reshaped into whole new sounds and ideas. There are no ripoffs. There only sounds in the atmosphere, repurposed and given new life. Legally, that might be an issue. Artistically, I think it’s fair game.
In a 2017 radio interview, Ice actually claimed that he’d bought the “Under Pressure” rights from Bowie and Queen, but a Queen spokesman said that Ice’s statement was wrong and that “an arrangement was made whereby the publishing in the song was shared.” In Jeff Weiss’ Ringer article, DJ Earthquake estimates that Queen, Bowie, and their publishers took 85% of the “Ice Ice Baby” royalties, which makes me wonder how there was any left over for Suge Knight.
“Ice Ice Baby” and “Under Pressure” are very different songs, but because he used that sample, Ice faced consequences, and so did the rest of rap. The attention surrounding that “Ice Ice Baby” sample made it prohibitively expensive for lots of rap producers to use sample collages in the way that they’d done before Vanilla Ice blew up. In the years ahead, the music was forced to change. These days, most samples on big rap songs are as obvious as the one on “Ice Ice Baby,” and rap producers face constant backroom negotiations about royalty rates and songwriting credits.
So Vanilla Ice changed rap. He made sampling more difficult. He became a walking example of what the genre should not be, thus possibly catalyzing a move toward meaner, harder sounds and lyrics. And Vanilla Ice took rap to vast audiences, many of whom were probably largely unfamiliar with the music. The success of “Ice Ice Baby” is a crucial pivot-point in the history of rap music. In my column on Mariah Carey’s “Vision Of Love” last month, I mentioned that I’m writing a book about the 20 most important #1 hits in the history of the Hot 100. Please believe that “Ice Ice Baby” is a chapter in that book.
Here’s something that I’m not mentioning in the book: When I was in high school, I bought a used copy of To The Extreme. (This was not an expensive proposition. In the late ’90s, used-CD stores were loaded down with copies of To The Extreme that they basically gave away.) I memorized “Ice Ice Baby” — or maybe re-memorized it — and I would rap that entire song constantly. I did it at parties, at school, and maybe onstage at a punk show once? I forget. This was an ironic thing, but I’m not sure whether I was making fun of the song or myself. Even though it was a joke, rapping that song was fun. It was stupid, but my dorky-ass friends always seemed excited to hear it, and I always got caught up in the moment. Maybe that’s how Vanilla Ice felt during that brief window of time that he wasn’t some kind of public pariah.
To The Extreme is a truly poor album, which probably helped ensure that Ice wouldn’t stick around. “Play That Funky Music” followed “Ice Ice Baby” into the top 10, but a third single, the absolutely godawful moony-eyed ballad “I Love You,” peaked at #52. In the movie Cool As Ice, Ice plays a biker who cruises through a small town, falls in love, and foils a kidnapping. I have a certain affection for Cool As Ice, but it’s definitely not a good movie. Cool As Ice arrived in theaters in October of 1991, after Ice had already become a laughingstock, and it flopped catastrophically. The soundtrack single “Cool As Ice (Everybody Get Loose),” a collaboration with the model Naomi Campbell, peaked at #81, and that was Vanilla Ice’s last time on the Hot 100.
Vanilla Ice’s next few years were checkered. He appeared in Madonna’s Sex book. He became a competitive jet skier. He attempted suicide via heroin overdose. He grew out dreadlocks. He followed up To The Extreme with 1994’s Mind Blowin’, an album where he tried to shed his image and catch up to a Death Row world. It didn’t work.
In 1998, Ice formed a nü-metal band and recorded the album Hard To Swallow with Korn/Limp Bizkit producer Ross Robinson. (Scott Shriner, his bassist, joined Weezer a few years later, and he’s been in that band ever since. Shriner plays on Weezer’s highest-charting single, 2005’s “Beverly Hills,” which peaked at #10. It’s a 7.) The single from Hard To Swallow was “Too Cold,” a rap-metal reimagining of “Ice Ice Baby.” Even when Vanilla Ice was attempting to radically reshape his image, he had no interest in getting away from “Ice Ice Baby.” When Ice was touring with that rap-metal band, I went to see him at the 9:30 Club in Washington, DC, and I’m pretty sure that Skarhead, the gooned-out New York hardcore band, was his opening act. I don’t remember that show too well, but I think I had fun.
In 1999, while Ice was promoting Hard To Swallow, he appeared on Lame 25, an MTV special about the worst videos in the network’s history. Hosts Jon Stewart, Janeane Garofalo, Denis Leary, and Chris Kattan watched those videos and snarked about them, and then those videos were supposedly banned from MTV thereafter. They invited Ice to destroy a VHS copy of his own “Ice Ice Baby” video, and Ice took things further, basically wrecking the entire set. The comedians seemed physically afraid.
In the 21st century, Vanilla Ice has carved out a strange career on the pop-cultural margins. He’s been in three Adam Sandler movies. He’s recorded for Psychopathic Records, the indie label founded by the Insane Clown Posse, and become a regular at the Gathering Of The Juggalos. He’s hosted nine seasons of The Vanilla Ice Project, a home-improvement show on the DIY Network that’s all about his house-flipping hustle.
A few months ago, Vanilla Ice performed alongside fellow past Number Ones artists like the Beach Boys, Berlin, and Taylor Dayne at a New Years party at Donald Trump’s Mar-A-Lago estate. (Ice later claimed that the party was “awesome” and “not about politics at all.”) Ice has also been arrested a bunch of times, for things like spousal abuse and burglary. Vanilla Ice’s legacy is a complicated one, and it seems to get more complicated all the time. Ice won’t be in this column again, but we’ll be looking at the aftershocks of “Ice Ice Baby” for a long time.
Yo man, let’s get out of here. Word to your mother.
BONUS BEATS: I didn’t mention one key chapter in Vanilla Ice’s journey to punchline status. In February of 1991, Jim Carrey played Vanilla Ice in an In Living Color parody that brutally depicted Ice as a hopelessly clueless white rap interloper. Here’s the “White White Baby” sketch, which remains both brilliant and scorching today:
Since then, there’s been a surprising amount of Jim Carrey/Vanilla Ice overlap. In the 2003 prequel Dumb and Dumberer: When Harry Met Lloyd, Derek Richardson, playing a younger version of Carrey’s Harry Dunne character, dances to “Ice Ice Baby” in the opening credits. Maybe that’s a nod to Carrey’s Ice impression, and maybe it’s just a stupid joke. Either way, here it is:
“Ice Ice Baby” also shows up on the soundtrack of one actual Jim Carrey movie. For reasons that are presumably ice-related, “Ice Ice Baby” is the closing-credits song for 2011’s Mr. Popper’s Penguins:
BONUS BONUS BEATS: Here’s Vanilla Ice’s fellow early-’90s Gumby-fade white rapper Kid Rock briefly sampling “Ice Ice Baby” on his 1992 track “Killin’ Brain Cells”:
(Kid Rock’s highest-charting single, the 2002 Sheryl Crow duet “Picture,” peaked at #4. It’s an 8.)
BONUS BONUS BONUS BEATS: Here’s the scene from 2004’s 13 Going On 30 where Jennifer Garner is utterly appalled at Samuel Ball’s “Ice Ice Baby” striptease:
BONUS BONUS BONUS BONUS BEATS: For my money, the single best pop-cultural use of “Ice Ice Baby” is in Adam McKay’s 2008 masterpiece Step Brothers, where Adam Scott lip-syncs to the song. Here’s that scene:
BONUS BONUS BONUS BONUS BONUS BEATS: Here’s the great Detroit underground rapper Sada Baby going in over an “Ice Ice Baby” sample on his 2019 mixtape track “Skanilla Ice”:
(Sada Baby’s highest-charting single, 2020’s “Whole Lotta Choppas,” peaked at #35.)