Robert Van Winkle, better known to the world as the one and only Vanilla Ice, was the first musician ever to top the pop singles charts with a rap song; it was to be his only number one hit. As a result of the unbelievably huge success of the song Ice Ice Baby and the resulting confusion, money grab, and mismanagement, Vanilla Ice is today thought of as something of a joke. This isn't really a clear representation of the facts; a better view would be that he simply took the money and ran.
Part of the difficulty with writing about Vanilla Ice is that he has made so many ridiculous claims (claiming to grow up in the projects, claiming to be a gang member, etc.) that it is hard to separate fact from fiction. Most of what follows sticks to verifiable fact, rather than Vanilla's PR.
Robert Van Winkle was born on Halloween, 1968, in the outskirts of Miami, Florida. He grew up in the suburbs listening to Motown records and some of the earliest rap stars and songs, like the Sugar Hill Gang and their early rap hit, Rapper's Delight. Influenced by this, he began to tour the south in the mid-1980s, performing at a variety of African-American dance clubs. He became somewhat popular in the Dallas, Texas area, and as a result some of his records began to receive some radio play there. One of his singles was being played on the radio at a Dallas station one fateful night in 1988, when the DJ accidentally played the b-side of the single, which had previously been completely ignored. That b-side was Ice Ice Baby, and while the song was playing, the station's switchboard lit up with calls from people interested in the song.
As Vanilla gained a following in the Dallas area, he came to the attention of the rap group Public Enemy in 1990, who wanted to sign him to their label. However, the group was unable to find a place for Vanilla, so Chuck D of Public Enemy personally gave Vanilla's name and demo tape to Capitol Records, who signed him on the spot. Vanilla spent the summer recording his first album, To The Extreme, and in the late fall of 1990, the label released his first single, Ice Ice Baby.
Thanks to heavy MTV exposure and radio play, the song took off and topped the pop charts as the end of 1990. The label had decided not to release a commercial version of the single, and instead released the album featuring the song in late 1990, just before Christmas. Fueled by Christmas sales, To The Extreme screamed up the charts, eventually hitting the top and staying there for seventeen weeks in late 1990 and early 1991. Vanilla Ice was on top of the world.
However, the decisions of what to do next were badly bungled by his management team, and in a desire to get as rich as he could as quick as he could, Van Winkle went along with it. They released a biography of Van Winkle, chronicling a false background story detailing his early life in the ghetto, trying to give the suburb-raised Van Winkle street credibility that he didn't have. They also attempted to make him look and act like a duplicate of contemporary rap star, MC Hammer. They toured together for a while, dressed nearly identically in sequin-heavy clothing and with elaborate dancing onstage. This is in sharp contrast to his original look and nature, which can be seen in the Ice Ice Baby video, where he is clad in sweatshirt and blue jeans.
The first real sign that things were headed down a rocky road for Vanilla (smell the pun!) was in February of 1991, when he was hit with the threat of a major lawsuit due to his hit song Ice Ice Baby. It turns out that the infectious beat of the song was stolen wholesale from the 1982 Queen and David Bowie collaboration, Under Pressure; they would go on to receive a large percentage of the revenue from the album and use of the song as the result of an out of court settlement.
Since he was being handed quite a lot of cash by his management and his record label, Vanilla bought in to the whole thing big time. He was a constant on MTV throughout early 1991, pandering to the pre-teen crowd like a madman. The station built up a month of hype for the debut of his second single, Play That Funky Music (White Boy)... and the single utterly tanked in the late spring of 1991.
At the time, he didn't really notice. He was filming a movie in the spring of 1991, called Cool As Ice. Probably the only thing worth mentioning from this film, which sums up the level of quality quite well, is the scene where Vanilla says to the female lead, "It's time to drop the zero and get with the hero." Did someone think that dialogue like this would make this movie a hit? The film came out in the fall of 1991 and utterly tanked; the film's soundtrack stayed on the Billboard charts for fewer weeks than To The Extreme had sat at number one.
His popularity had vanished due to poor marketing, mostly. Fans were fed up, not so much with the music (he was very good with a catchy beat), but with his image. He often used extremely corny dialogue such as the line quoted above, he wore sequined jumpsuits, and he constantly pandered to a very fickle pre-teen crowd who was mostly just interested in his first hit single. Add these all up and you have a one hit wonder.
Vanilla Ice laid low after the failure of Cool As Ice, only reappearing in 1992 contributing the song Ninja Rap to the soundtrack to the second Teenage Mutant Ninja Turtles movie soundtrack. He became a major player in the motocross circuits, until 1994, when he released the album Mind Blowin'. Rather than sticking with the pop sound that had served him in the past, he used a ton of drug references and a "gangsta rap" sound quite imitative of Cypress Hill. The album tanked again; using the name Vanilla Ice conjured up images of "It's time to drop the zero and get with the hero." and sequined jumpsuits, not gangster rap. After this failure, he was dropped by Capitol Records.
In 1998, he was signed by Universal Records and released a new album, Hard To Swallow. This time, he attempted to sound like the popular rap-rock fusion bands of the day, such as Korn and Limp Bizkit. Again, he couldn't move past his previous image; again, the album tanked. Since then, he has remained underground, occasionally reverting to his pop stylings, but usually following whatever trend is hot at the moment.
One shouldn't feel sorry for Vanilla, however; he is quite rich at this point in his life, with enough money such that he doesn't have to work again. His legacy will be with one hit song... and a lot of bad decisions.