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File:Photo-vanilla ice-122709 3916.jpg

Vanilla Ice, real name Robert Van Winkle (1967-, not to be confused with Rip Van Winkle), is a rapper born in Dallas, Texas, and raised in Texas and South Florida, who is best known for his 1989 hit "Ice Ice Baby", which samples the main riff from Queen and David Bowie's "Under Pressure". Between the ages of 13 and 14, Van Winkle practiced breakdancing, which led to his black friends calling him "Vanilla Ice." Van Winkle wrote "Ice Ice Baby" at the age of 16, basing its lyrics upon his experiences in South Florida.

In 1987, Van Winkle met Tommy Quon at his Dallas night club City Lights. Upon seeing Van Winkle's performance, Quon saw commercial potential in his rapping and dancing skills, and offered him a contract with his management company, Ultrax. Van Winkle signed a contract with Ichiban Records in 1989, and released his debut album, Hooked. "Play That Funky Music" was released as the album's first single, with "Ice Ice Baby" appearing as the B-side. When a disc jockey played "Ice Ice Baby" instead of the single's A-side, the song was more popular than "Play That Funky Music". Quon financed $8000 for the production of a music video for "Ice Ice Baby", which received heavy airplay by The Box, increasing public interest in the song. Van Winkle later opened for EPMD, Ice T, Stetsasonic and Sir Mix-A-Lot on the Stop the Violence Tour.

However, Van Winkle's success did not go without drama. After signing with a larger label, SBK, they paid him to adopt a more commercial appearance, which was the subject of frequent mockery among his peers. Quon attempted to expand Van Winkle's success into film, with mixed results. He had a cameo in Teenage Mutant Ninja Turtles II: The Secret Of The Ooze, which was a success (but not really because of Ice). Ice also starred in the vehicle Cool as Ice, which bombed at the box office, earned him a Golden Raspberry Award for Worst Actor, and today isn't even watchable as an early '90's artifact. SBK and Quon also pretty much ruined his reputation by publishing a fake autobiography without his knowledge which claimed a violent gang life that he didn't participate in. Van Winkle soon found himself having to answer questions about claims he never made, and the inconsistency between the label's biography and Van Winkle's actual statements led to further criticism.

Van Winkle attempted to take control of his career by releasing Mind Blowin, without any "image", and with harder lyrics, and a live, funk-oriented sound. The label went bankrupt during the album's release, however, and it was poorly received. Van Winkle began using harder drugs than previously, and attempted suicide through a drug overdose. When he survived, he was inspired to not only clean up his act (he now only smokes marijuana), but to remove himself from the public spotlight completely. After playing in a couple of Miami grunge bands, and trying to move toward a more rock oriented sound, he teamed up with producer Ross Robinson and releasing the album Hard to Swallow, which earned him a new fanbase which enjoyed his new sound. Since then, he has had some success on the independent music scene, with less mainstream albums featuring a style that he refers to as "Metal Molten Hip Hop". He's even had quite a few appearances in film and TV, including The Surreal Life (which included a hilarious scene where he antagonized Gary Coleman), The New Guy and Big Money Rustlas. Most recently, he has starred in The Vanilla Ice Project on the DIY network which is... a home improvement show. As it turns out, Robert's other pastime to rapping is home improvement and real estate (and he's pretty good at it; it's his other job when he isn't touring). His other other pastime is extreme sports - he even won a few championships. The Vanilla Ice Project has been successful enough to be picked up for a second season - as a result, expect more odd occurrences of a hardcore rapper saying things like "Mmm. They smell great. I love flowers. They're great."

Van Winkle has been called "The Jackie Robinson of Hip Hop" by Public Enemy leader Chuck D, and was one of the earliest examples of a white rapper achieving a large level of success, after the groups Beastie Boys, 3rd Bass and House of Pain, but preceding successful solo acts like Kid Rock and Eminem. Having been raised in both Dallas and Miami, Van Winkle is the most successful rapper from these cities. "Ice Ice Baby" was so popular that it has remixed multiple times, and was the subject of a cover by Irish pop duo Jedward, as a mash-up with "Under Pressure", the song that it famously sampled.In 2011, he signed to Psychopathic Records. Critics also liked his performance as Captain Hook in a pantomime stage production of Peter Pan.


  • To the Extreme (1990)
  • Extremely Live (1991)
  • Mind Blowin (1994)
  • Hard to Swallow (1998)
  • Bi-Polar (2001)
  • Platinum Underground (2005)
  • WTF (2011)

Vanilla Ice demonstrates the following tropes:

  • Boastful Rap: Frequently, although it could be argued that many rappers do this.
  • Creator Backlash: For a while, any material from To the Extreme was off-limits, but he still performs "Ice Ice Baby", and even recorded a Nu-metal version, "Too Cold", in 1998.
  • Darker and Edgier: Hard to Swallow is much darker than any album Vanilla Ice has made before or since.
  • Hair-Trigger Temper: On The Surreal Life, he lost a game and proceeded to trash his room (including throwing a drum kit and nearly clobbering Ron Jeremy in the process), trash the set, cut his own hand open after punching a light, and sent the cast running for their lives.
  • High Altitude Interrogation: Suge Knight of Death Row Records implied to Van Winkle that Knight would have his thugs throw him over a balcony unless Van Winkle signed over the rights to "Ice, Ice Baby." Tabloid rumors suggested that Knight did this, rather than simply implied it.
  • Hip Hop
  • Hypocritical Humor: An unintentional example happened on the Reality TV show The Surreal Life, which featured several former stars living together, including Vanilla Ice. Rob would often get very upset if anyone brought up Ice Ice Baby or simply talked about his former celebrity status, even going so far as to refuse to be called Vanilla Ice. Gary Coleman appeared on one episode for a charity event (he was running for the governor of California at the time). Vanilla Ice demanded that Coleman say his old Catch Phrase from Different Strokes, "Whatchoo talkn' `bout Willis?". Coleman refused and Vanilla Ice went so far as to pick him up and carry him around in order to force Coleman to say something that he hadn't said since he was twelve. Vanilla Ice eventually claimed Coleman was being too serious about his former celebrity status and did not see the hypocrisy of the situation. The audience did, however.
  • Identical Stranger: Rob and Fred Durst.
  • Juggalo: Frequently seen wearing the Hatchetman charm, he finally signed with Psychopathic Records in 2011, after years of rumors. He also delivered the Crowning Moment Of Funny at the end of ICP's Bizaar; ICP appear on his song "Insane Killas" (from his Bi-Polar album), and he appears on "Swallow This Nut", which was released on ICP's Forgotten Freshness Vol. 4. It's... quite something to hear him match Violent J Cluster F-Bomb to Cluster F Bomb...
  • Metal Scream
  • New Sound Album:
    • Mind Blowin (1994) featured largely live instrumentation and funk elements, compared to his debut album, To the Extreme, which was largely synthesized and Hip Hop-oriented.
    • Hard to Swallow (1998) was largely Nu-metal, with the exception of "Freestyle", which was hip hop.
    • From Bi-Polar (2001) on, his albums have been pretty consistent sound-wise, mixing hard rock/rap-metal/nu-metal and hip hop tracks...
    • Except for WTF (2011), which has a lot of electro-based fusions, and even a couple of Country Rap songs with Cowboy Troy.
  • Non Actor Vehicle: Cool as Ice, effectively a remake of Rebel Without a Cause.
  • Old Shame: He strongly regrets the clothing his label forced him to wear in the early '90s.
  • Pretty Fly for a White Guy /TastesLikeDiabetes /AmbiguouslyGay: At least his early 1990s incarnation. The picture shows he's gotten better.
  • Rap Rock Rap Metal Punk Rap Nu-metal Metal Molten Hip Hop.
  • Sex, Drugs and Rock and Roll
  • Shrouded in Myth: He was very secretive about his personal life, with the intention of protecting his family. In an attempt to rectify this, his former label wrote a fake biography in his name and tried to pass it off as his official life story without his knowledge, and ended up creating even more myths. Van Winkle's own account of his life is not as exciting as his label tried to make it out to be, the only truth to it being that he did grow up in a poor neighborhood.
  • Signature Song: "Ice Ice Baby"
  • Token White
  • Two Hit Wonder: Even though he is only remembered for one of those hits.