Although Van Winkle was successful, he later regretted his business arrangements with SBK, which had paid him to adopt a more commercial appearance to appeal to a mass audience and published fabricated biographical information without his knowledge. After surviving a suicide attempt, Van Winkle was inspired to change his musical style and lifestyle. While later albums by Van Winkle haven't charted or featured much radio airplay because of their less mainstream, rock-oriented sound, Vanilla Ice has had a loyal underground following. In 2009, Van Winkle began hosting The Vanilla Ice Project on DIY Network. His latest album WTF – Wisdom, Tenacity & Focus was released in August 2011. Van Winkle is currently signed to Psychopathic Records.
Robert Matthew Van Winkle was born in Dallas,
Texas Van Winkle never knew his real father, and was given
the family name of the man his mother was married to at the time
of his birth. Because of his parents' divorce, he grew up moving
between Dallas and Miami. Van Winkle's stepfather was a car
salesman. Hip hop had an impact on Van Winkle at an early age,
saying "It's a very big passion of mine because I love poetry. I was just heavily influenced
by that whole movement and it's molded me into who I am today."  Between the ages of 13 and 14, Van Winkle practiced breakdancing, which
led to his friends nicknaming him "Vanilla", because he was the only one in the group that wasn't African American.
Although he disliked the nickname, it stuck. Shortly afterward,
Van Winkle started battle rapping at parties and because of his
rhymes, his friends started calling him "MC Vanilla", however when he became a member of a breakdance troupe, Van Winkle's stage
name was "Vanilla Ice" combining his nickname "Vanilla" with one of his breakdance moves, the "Ice" Van Winkle wrote "Ice Ice Baby" at the age of 16, basing its lyrics on a weekend he had with friend and band
member D-Shay in South Florida. The lyrics describe a drive-by
shooting and praise Van Winkle's rhyming skills.
In 1985, Van Winkle was focusing all of his energy on motocross, winning three straight titles at the Grand National Championships in Dallas. After breaking his ankle during a race, Van Winkle was not interested in racing professionally for some time, using his spare time to perfect his dance moves and creating his own while his ankle was healing. Van Winkle used his beatboxing and breakdancing skills as a street performer with his friends at local malls. One evening he visited City Lights, a Dallas night club, where he was dared to go on stage by his friend Squirrel during an Open Mic. He won the crowd over and was asked by local disc jockey Floyd 'Earthquake' Brown if he wanted to perform regularly which he accepted. Earthquake would sometimes be joined by Ice's own disc jockeys D-Shay and Zero. Ice's breakdance group named itself 'The V.I.P.' (the Vanilla Ice Posse) and performed with him on stage. As a performer for City Lights, Ice opened up for N.W.A and MC Hammer.
In 1987, Van Winkle met the owner of City Lights, Tommy Quon. 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. Recording songs that had been perfected on stage by Ice and his acquaintances with various producers, the two year production was distributed by independent record company Ichiban Records. In 1989, Van Winkle's debut album Hooked was released and sold 48,000 copies in the Texas area." Play That Funky Music" was released as the album's first single, with "Ice Ice Baby" appearing as the B-side. Tommy Quon personally sent out the single 'Play That Funky Music' alongside 'Ice Ice Baby' on its B-Side to various radio stations around the US, but the single was seldom played and when it was, it did not get the attention Quon was hoping for. When disc jockey Darrell Jaye in Georgia played "Ice Ice Baby" instead of the single's A-side, the song gained a quick fanbase and other radio stations followed suit. Quon financed $8,000 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.
Following the success of "Ice
Ice Baby", record producer Suge Knight and two bodyguards arrived at The Palm in West
Hollywood, where Van Winkle was eating. After shoving Van Winkle's
bodyguards aside, Knight and his own bodyguards sat down in front
of Van Winkle, staring at him before finally asking "How you doin'?" Similar incidents were repeated on several occasions. Eventually, Knight
showed up at Van Winkle's hotel suite on the fifteenth floor of
the Bel Age Hotel, accompanied by a member of the Oakland Raiders.
According to Van Winkle, Knight took him out on the balcony by
himself, and implied that he would throw him off the balcony unless
he signed the publishing rights to the song over to Knight; Knight
used Van Winkle's money to help fund Death Row Records.
On the basis of Van Winkle's good looks and dance moves, Public Enemy tried to convince their producer, Hank Shocklee, to sign Van Winkle to Def Jam, but Van Winkle later signed a contract with SBK Records in 1990. SBK remixed and re-recorded Hooked under the title To the Extreme. The reissue contained new artwork and music. According to Van Winkle, SBK paid him to adopt a more commercial, conventional appearance. This led Van Winkle to later regret his business agreements with SBK.
SBK Record executive Monte Lipman stated that he received calls from radio stations reporting over 200 phone calls requesting Ice Ice Baby. SBK wanted Ice on the road as soon as possible. MC Hammer, an old acquaintance from his club days, had Ice on as an opening act on his tour.
To the Extreme became the fastest selling hip hop album of all time, peaking at #1 on the Billboard 200. The album spent 16 weeks on the charts, and sold eleven million copies. Reviews of To the Extreme were mixed. Entertainment Weekly reviewer Mim Udovitch gave the album a B, citing "Ice Ice Baby", "Play That Funky Music", "Dancin'" and "It's a Party" as the album's highlights. Robert Christgau gave the album a C− rating, writing that Van Winkle's "suave sexism, fashionably male supremacist rather than dangerously obscene, is no worse than his suave beats". Criticizing the technique and style of Vanilla Ice, Allrovi reviewer Steve Huey wrote:
Ice's mic technique is actually stronger and more nimble than MC Hammer's, and he really tries earnestly to show off the skills he does have. Unfortunately, even if he can keep a mid-tempo pace, his flow is rhythmically stiff, and his voice has an odd timbre; plus, he never seems sure of the proper accent to adopt. He's able to overcome those flaws somewhat in isolated moments, but they become all too apparent over the course of an entire album.
In late 1990, Van Winkle began an eight-month relationship with Madonna, and appeared in photographs for her book, Sex. In the height of Van Winkle's popularity, SBK licensed a 12" doll which was made by THQ. In January 1991, he was the musical guest on Saturday Night Live. Van Winkle branched out into the film industry with an appearance in the film Teenage Mutant Ninja Turtles II: The Secret of the Ooze, which he later called "one of the coolest experiences" of his career. Van Winkle 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. While on tour in 1991, Van Winkle found out that SBK had instigated the publication of the biography which detailed false biographical information, including claims that he had attended school with Luther Campbell and over exaggerating his living conditions in Miami.
Van Winkle's second major release was the live album Extremely Live, released in March 1991. The album was a live recording during Vanilla Ice's performance in Miami during his To The Extreme tour. Premiering new songs like Rollin' in My 5.0, Road To My Riches and Satisfaction, the album peaked at #30 on the Billboard 200, but it received mainly negative reviews, with Entertainment Weekly reviewer David Browne calling it "one of the most ridiculous albums ever released", comparing it to The Best of Marcel Marceau, an album which consisted of two sides of silence opened by brief applause. According to Browne, Extremely Live "affords you the chance to hear inane stage patter [...] and unaccompanied drumming, during which, one assumes, Ice and his posse are onstage dancing." Monte Lipman later stated that SBK only released the live disc to make more money from Ice's fame. In April 1991, Van Winkle began to film the SBK produced Cool as Ice, in which he played a leading role.
Cool as Ice opened on October 18, 1991 in 393
theaters in the United States, grossing $638,000, ranking at #14
among the week's new releases. Reviews of the film were negative.
Film website Rotten Tomatoes, which compiles reviews from a wide
range of critics, gives the film a score of 8%. Van Winkle
received a Golden Raspberry Award for Worst New Star. SBK stated
that they overexposed Ice and Van Winkle decided to stop taking
their business advices as well as distancing himself from the image
that SBK was trying to create for him. In late 1991, Ice appeared
in the Circus of the Stars and Sideshow, driving his motorcycle
through a wall of fire. While his fame in the United States had
severely dropped, Ice continued performing to sold out crowds in
his 1992 world tour, playing in South America, Europe, Australia
and Asia, premiering new songs like "Get Loose", "The Wrath", "Now & Forever", "Where the Dogs At? (All Night Long)", "Minutes of Power" and "Iceman Path". Van Winkle also served as a spokesperson for Nike and Coca-Cola throughout
1991 and 1992.
After almost nothing but non-stop touring for the past three years, Van Winkle took a small break from music in 1993 and started competing in Jet skiing under his real name. In 1993, most members of the V.I.P. (Vanilla Ice Posse) had gone their separate ways, including Ice's disc jockey Earthquake. Ice's hype man and second disc jockey Zero, became Ice's DJ full time. In late 1991, Ice had started production on his second album, Mind Blowin, but continuous touring in 1991-1992 delayed the album severely. Van Winkle was interested in responding to his critics by having his next album surpass his earlier and popular work. In 1992, Ice started writing response songs aimed at 3rd Bass and Marky Mark and the Funky Bunch. Together with Zero, the new album started production yet again, scrapping a lot of finished songs and re-doing others. Zero would help create new beats to songs that Van Winkle had already performed live such as "The Wrath", while other songs like "Iceman Path" and "Get Loose" were left unchanged. In 1993, Ice toured Eastern-Europe again and premiered songs off his upcoming album in St. Petersburg, Russia in front of President Boris Yeltsin. During months of non-stop touring, Van Winkle and the remaining back-up dancers smoked cannabis regularly after a show.
By 1994, Van Winkle received less publicity and became removed from the public spotlight. After becoming more interested with the Rastafari movement, Van Winkle became a vegetarian, grew dreadlocks and talked more openly about smoking cannabis. On March 22, 1994, Van Winkle released his second studio album, Mind Blowin. Reviews were unfavorable. Entertainment Weekly reviewer James Bernard called the album "more clunky than funky". Rolling Stone reviewer Danyel Smith praised the song "Get Loose" as "snappy", writing that although the lyrics are "inane", "the song is a thumping party, one of the few places where Ice loosens up. He sounds solid at the beginning of 'The Wrath' as well [...] In 'Now and Forever,' a wet dream kind of song, Ice goes back to goofy lyrics." Allrovi reviewer Stephen Thomas Erlewine wrote that "There isn't a single moment that establishes a distinct musical identity, and the whole thing is rather embarrassing." Primus bassist Les Claypool stated in response to Van Winkle's cannabis-oriented lyrics: "That's all fine and dandy and cute, but it could be misconstrued and manipulated by the wrong people." When asked about the drug oriented sound years later, Vanilla Ice said "A lot of the record is drug oriented because I was doing a lot of drugs at the time". Shortly afterward, SBK went bankrupt.
At around this time, Van Winkle began using ecstasy, cocaine and heroin. During periods of heavy drug use, Van Winkle received many tattoos from artist acquaintances. According to Van Winkle, he "was in [his] binge days. [He] didn't even realize how many [he] was getting". Van Winkle attempted suicide with a heroin overdose on July 4, 1994 but was revived by his friends. After being revived, Van Winkle decided that it was time to change his lifestyle. As a symbol of his attempt to begin anew, he got a tattoo of a leaf on his stomach. Van Winkle sold his estate in California and moved back to Florida and took a break from music, rather focusing on motocrossing and jet skiing. By the summer of '95 Van Winkle was the world's No. 6-ranked sit-down Jet Ski racer, competing nearly every weekend and earning a Kawasaki sponsorship. He met future wife Laura Giaritta a year after his suicide attempt at a Fourth of July party in 1995.
Uncertain about his future career, Van Winkle
studied real estate and started working on the side renovating
and selling houses. In 1995, Van Winkle set up a recording studio
in Miami and joined a grunge band, Pickin Scabz. The name was set
to reflect Van Winkle's career and how he was healing from his
suicide attempt and that he was now "picking up the pieces". Van Winkle expressed an interest in performing hip hop-influenced rock
music, but found that the band was unable to produce the sound
he was looking for. Van Winkle performed his set from Mind Blowin
in a tour around Russia in 1995 after getting multiple requests
to return after his debut there in 1993. In 1996, long time
associate and friend Monte Lipman signed Van Winkle as an artist
for Universal Republic Records. He did guest vocals with no stage
name for the song "Boom" by Bloodhound Gang on their CD One Fierce Beer Coaster, which at the time was
possibly Van Winkle's last venture into music. Later that year,
Van Winkle opened up a Miami-based Extreme sport store that focused
mostly on water sports and surfing, which he and girlfriend Laura
named after his first mainstream album, '2 The Xtreme'. On March
30, 1997, Van Winkle married Laura. His relationship and different
professions helped anchor Van Winkle, who planned on leaving music
behind just as he did hard drugs.
Van Winkle later developed a friendship with producer Ross Robinson, who had become known for producing music by Deftones, Korn, Limp Bizkit and Sepultura. Robinson and Van Winkle shared an interest in motocross racing. According to Robinson, others had attempted to discourage him from working with Van Winkle, saying it might hurt his reputation. Rather than being dissuaded, their fear encouraged Robinson who agreed to work with Van Winkle. In an interview, Robinson stated "It's the most punk-rock thing you could do."
Van Winkle started talking very openly about his early business ventures in interviews while the album was being recorded. Appearing in interviews and TV documentaries about his former image, selling out and his run-ins with Suge Knight. Despite not being happy with his old image, Winkle stated that he never had a problem with his older music. Van Winkle decided against changing his stage name to something else, as he felt no need to run from his past, despite being uneasy with some of it.
Van Winkle's third studio album, Hard to Swallow, featured a darker sound and lyrics than Van Winkle's previous work as well as various mixtures of different styles of hip hop and hard rock which caught the media's attention. Van Winkle attracted a whole new audience when he started touring again, some who were even unfamiliar with his more mainstream sound. Despite getting its own audience and going Gold, reviews of the album were generally negative. Jon Pareles of The New York Times wrote that "If history is any guide, Vanilla Ice's adoption of rap-metal means that hard rock is about to move on." Richard Torres of Rolling Stone gave the album two out of five stars, writing that while "nothing, however, can redeem Ice's wack boasting," the album "isn't half-bad." In The New Rolling Stone Album Guide, Rob Kemp gave the album three out of five stars, writing that it contained Van Winkle's "most convincing music". A lot of executives at SonyBMG were predicting that the album would do better than 'To The Extreme'. In promotion of Hard to Swallow, Van Winkle toured with a seven-piece live band which included bassist Scott Shriner. The band opened with rock-oriented material from Hard to Swallow and concluded with older hip hop songs. The setlist also included "Power", based upon Led Zeppelin's "Immigrant Song". Van Winkle said that writing the songs and performing them were like therapy, as he had tried to hide his anger when making his older songs but Robinson was the first producer who told him to use it to create.
In 1999, the music video for "Ice Ice Baby" was "retired" on the MTV special 25 Lame, in which Van Winkle himself was asked to destroy the video's master tape. When Van Winkle was given a baseball bat, he ended up destroying not only the film but the show's entire set as well. In 2001, DJ ReAnimator remixed "Ice Ice Baby" with Vanilla Ice re-doing his vocals for the track. Ice Ice Baby 2001 was released as a single and music video for the European market spawning a wave of overseas interest in Vanilla Ice.
Having attracted a following outside of his former mainstream audience, Van Winkle began recording independently, despite still being signed at Sony. During a recording session, Ice met the all-female American hard rock band from Southern California, Betty Blowtorch. The late Bianca Halstead bonded with Van Winkle and asked if he wanted to contribute a rap interlude to the their track Size Queen. On Van Winkle's collaboration with the band, lead vocalist and bassist Halstead was quoted saying "'Do you wanna talk about how big your dick is on our record?' He said, 'Sure.' I asked him if he could rap over [the track] and he said he can rap over anything. And he could!"  Per his stepfather's request, Van Winkle started working with his former manager Tommy Quon again, while hoping to re-create some of the magic that they worked hard on in the early 90's, Van Winkle denied any interest in trying to become big again and that his only passion was music, not fame.
In May 2000, Van Winkle wrestled in a match promoted
by Juggalo Championship Wrestling, then known as Juggalo Championshit
Wrestling, filling in for Insane Clown Posse member Joseph Utsler,
who had been injured during a match. MTV News reported that
Insane Clown Posse would make an appearance on Van Winkle's next
album, tentatively titled Bomb Tha System. In October 2000,
Van Winkle announced that his next album would be titled Skabz,
and that Chuck D was confirmed to appear on the album. It was initially
planned as a double album featuring a disc containing rock-oriented
material and a disc of hip hop songs. In July 2001, Van Winkle
performed at the second Gathering of the Juggalos. On October
23, 2001, Skabz and Bomb Tha System were released as a single album,
Bi-Polar. The album also featured La the Darkman, Pearla, Insane
Poetry and Bob Kakaha. Bradley Torreano of Allrovi disliked the
album, criticizing it as "wildly uneven and at times hilariously bad", but also stating "Vanilla Ice is still better than a lot of the rap-metal bands that erupted in
2000/2001." and the rap beats on Bomb Tha System "are surprisingly solid". In The New Rolling Stone Album Guide, Rob Kemp gave the album one out of
five stars, calling the album "utterly listless". According to a Sony BMG executive, sales of Bi-Polar were "not bad...for Vanilla Ice. That's pretty respectable. Seriously."
After the release of Bi-Polar, Van Winkle left Sony-Universal to be with Ultrax full time. With Quon back as manager, Van Winkle was scheduled to appear in various reality TV programs. Ice, still an entertainer at heart felt that the experience would be good for him. In 2002 he appeared on Celebrity Boxing, fighting Todd Bridges under the name 'Bi-Polar'. In 2003, he appeared in five episodes of Hollywood Squares, eight episodes on 'The Farm' and three episodes of Celebrity Bull Riding Challenge as well as a cameo in The New Guy in 2002.
Van Winkle continued motocrossing and auditioned for the 2002 X Games in the freestyle division and was placed seventh at the 2003 Suzuki Crossover challenge. In 2003, Van Winkle contributed vocals to "Off the Chain" by 7x70, a side project of Iron Maiden drummer Nicko McBrain and Anthrax guitarist Dan Spitz. A demo of the song was leaked in June. In 2003, Ultrax reissued Bomb Tha System (the second part of "Bi-Polar") under the title Hot Sex, which was a single from the original album.
From January to February 2004, Van Winkle appeared on the reality television series The Surreal Life. Although much of the series was staged, Van Winkle found the experience to be therapeutic, stating that a comment made by Tammy Faye Messner during filming; "We are who we are because of who we were" helped him accept his past. After filming 'Surreal Life', Van Winkle co-starred in the drug comedy The Helix...Loaded, an independent film parodying The Matrix and other movies made in the late 90's/early 00's. Van Winkle's song "Hot Sex" was featured on the soundtrack and the film featured a reference to "Ice Ice Baby".
On August 2, 2005, Van Winkle released his fifth studio album, Platinum Underground. Van Winkle stated that the title of the album reflected the fact that he could maintain a fanbase without mainstream airplay. Allrovi reviewer Rob Theakston panned the album, writing that it "has more bad spots in it than most". The album featured the song "Survivor" which had premiered on an NBC special produced in the UK entitled Hit Me Baby One More Time. Songs like Trailer Park Mullet Wars and Step Up or Shut Up were a hybrid mix of different heavy metal sounds, while Say Goodbye and Bounce were new school hip hop. The rest of the album featured mixes of Horrorcore, Reggae and Hardcore hip hop. After getting requests to do Ninja Rap live, Ice decided to make a song entitled Ninja Rap 2 (also known as Go Ninja Go) which was set to be a hardcore remix. Despite the name, the song has very little connections to Van Vinkle's original 1991 single, but rather stays true to Ice's current lyricism, where Ice talks about his appreciation to his fans, his love to perform at clubs and playing at the Gathering of the Juggalos with Insane Clown Posse. Ninja Rap 2 was the first song to be released from Platinum Underground and was available to download for free off of Ice's official website.
In 2007, Van Winkle returned to a spin-off to
The Surreal Life entitled The Surreal Life: Fame Games where he
again trashed the set after being voted off. In September 2008,
Van Winkle signed a contract with Cleopatra Records, recording
the cover album Vanilla Ice Is Back! at the label's request.
The album was released on November 4, 2008, and contained covers
of songs by Public Enemy, House of Pain, Bob Marley and Cypress
Hill. IGN reviewer Spence D. called the album "an embarrassing endeavor that sounds like it should have stayed locked inside
Ice's studio (or at the very least leaked on YouTube and passed
off as a piss take)." On February 27, 2009, Van Winkle performed as part of a joint performance
with MC Hammer in Orem, Utah called "Hammer Pants And Ice", which featured 24 dancers and a full choir.
Ice was a special musical guest at the 2010 National Television Awards in January, performing with Jedward for their remix and debut single "Under Pressure (Ice Ice Baby)". Van Winkle also recorded his verse for their album Planet Jedward and appeared in the music video. Vanilla Ice was a part of The Back2Kool concert tour with Turbo B and MC Hammer, playing in worldwide in late 2010. Ice reunited with his former DJ; Floyd 'Earthquake' Brown for the shows overseas.
In 2009, Van Winkle started filming a reality television series called The Vanilla Ice Project which premiered on DIY Network on October 14, 2010. The season is focused on renovating a house in Palm Beach, Florida with each episode dedicated to a different room in the house. In 2011, Van Winkle published his first book, Vanilla Ice Project – Real Estate Guide on how to succeed in real estate. The book was made available as a free digital download on his real estate website. The second season will air January 2012.
In August 2009, Van Winkle announced on his official Twitter account that he had signed a contract with StandBy Records, which was scheduled to release his sixth studio album, WTF; however, Van Winkle was later left the label. WTF was officially released on August 19 through Radium Records. In early 2011, Vanilla Ice appeared on the sixth season of the UK show Dancing on Ice as well as various ice skating tours surrounding the show.
In June 2011, Van Winkle filmed a role in the film I Hate You, Dad, portraying Antonio, Adam Sandler's best friend from high school. In August, Van Winkle performed at the 2011 Gathering of the Juggalos, where it was officially announced that he had signed with Psychopathic Records. Van Winkle will record an album for Psychopathic with production by Mike E. Clark. Joseph Bruce stated that it will be released between the end of 2011 and early 2012.
In December 2011, Van Winkle will portray Captain
Hook in the Chatham Central Theatre pantomime production of Peter
Pan alongside Henry Winkler.
Van Winkle married Laura Giaritta in 1997; the
couple split in 2011. They have two daughters, Dusti Rain (born
1998) and KeeLee Breeze (born 2000). Van Winkle is a Juggalo
and a Vegetarian.
On June 3, 1991, Van Winkle was arrested in Los Angeles on firearm charges, after threatening a homeless man, James N. Gregory, with a pistol. Gregory had approached Van Winkle's car outside of a supermarket and attempted to sell him a silver chain. Van Winkle and his bodyguard were charged with three weapons offenses. Van Winkle pleaded no contest.
In January 2001, Van Winkle was arrested by police in Davie, Florida for assaulting his wife, Laura. According to the criminal complaint, Van Winkle and his wife argued as they drove on Interstate 595. Van Winkle admitted to pulling hair from her head to prevent her from jumping out of the truck's window. He pleaded guilty to charges of disorderly conduct four months later, and was sentenced to probation and ordered to attend family therapy sessions.
Van Winkle's pet wallaroo, Bucky, and pet goat, Pancho, escaped from his Port St. Lucie, Florida home in November 2004. After wandering around local streets for over a week, the animals were caught, and returned to Ice. He had to pay a $220 fine for expired pet tags, and an undisclosed fine for the escape of the animals.
Van Winkle appeared in West Palm Beach court on September 2007 to be arraigned for driving with an expired license. In the months leading up to the court hearing, Ice had been pulled over for doing 74 in a 45-mph zone, violating high-occupancy vehicle-lane restrictions and having illegally tinted car windows.
On April 10, 2008, Van Winkle was arrested in
Palm Beach County on a battery charge for allegedly kicking and
hitting his wife. He was released the following day after she
declared that her husband had only pushed her. In court, the couple's
neighbor, Frank Morales, stated that it was merely a verbal argument.
Van Winkle was ordered by a Florida court to stay away from his
wife following his arrest, and to communicate with his children
only if Morales accompanied him. The judge told Van Winkle that
he could only contact his wife via telephone. On April 29,
2008, Van Winkle's lawyers, Bradford Cohen and Joseph LoRusso,
were able to get the case dropped after providing the state attorney
with evidence that conflicted with what was originally reported.
Van Winkle's current live performances feature a mix of newer, rock and techno-influenced material and old school hip hop. Van Winkle performs with a live drummer and DJ, and sometimes sprays his audience with bottled water. Van Winkle's performances often feature an inflatable grim reaper balloon, a dancer in a clown mask, and confetti thrown into the audience. Describing his performances, Van Winkle stated "It's high energy, stage diving, pyrotechnics, girls showing their breasts. It's crazy party atmosphere."
Van Winkle stated that his musical style was influenced by underground music, rather than mainstream music, and that his influences included hip hop and funk artists such as Funkadelic, Rick James, Roger Troutman, Egyptian Lover and Parliament. Van Winkle is a big fan of 50's and 60's Reggae and Bob Marley's work and has also stated that he enjoys Rage Against the Machine, Slipknot and System of a Down. After signing with Psychopathic Records, Violent J mentioned that Insane Clown Posse were long time fans of Ice's work; “We were bumping him way before "Ice Ice Baby" blew up. We were bumping him when he had his first record out on Ichiban. Shaggy had the vinyl and we used to bump that shit up in his room. It felt like two summers before that shit blew up.”
Van Winkle sometimes plays bass, drums and keyboards
on studio recordings. Vanilla Ice refereed to his mainstream
music as "above-ground" rather than underground, as he tried to make danceable beats and removed cussing
so that the songs could reach a wider audience. A lot of his early
hits had Ice boasting sexual conquests, in 1991, Van Winkle was
quoted "I rap about what I know. Girls and stuff. That's what is going through my head.". Ice's lyricism evolved with him and when asked about his darker sound in
2002, Ice replied; "Music is about reflection and I’m just reflecting my life and everything it’s
been and there’s no way I’m going to be able to stress what I want
and mean over a break beat, you know, it’s too emotional and it’s
too intense, so you have to have the intensity of the band, it’s
like a symphony, you know, you have to build on the intense parts,
and so it just wasn’t going to happen, to come extreme over some
hip hop record, so to exercise my demons I had to have the band." 
Along with Beastie Boys, 3rd Bass and House of Pain, Van Winkle was one of the earliest white rappers to attain major success. Chuck D has credited Van Winkle as a regional breakthrough, stating "He broke through in the mid-South, in a Southern area in Texas, in something that was kind of indigenous to that hip-hop culture down there. He just doesn’t get credit for it." Vanilla Ice was one of the first Caucasian rappers to gain worldwide fame and recognition and the first rapper to reach the Billboard 100. As a result of his success, Van Winkle was the subject of criticism from other hip hop musicians. After Van Winkle's early success on radio, Chuck D remembers "When ["Ice, Ice, Baby"] came out, black people liked it until they found out he was white, and three years later, no one would admit to buying his record." Radio personality Casey Kasem considered Vanilla Ice the #1 Rap Star in history.
In 1991, 3rd Bass released a single called "Pop Goes the Weasel", and in the lyrics comparing Van Winkle unfavorably to Elvis Presley. The song's music video featured Henry Rollins as Van Winkle, who is depicted as being assaulted by 3rd Bass. Del tha Funkee Homosapien referred to Van Winkle in the lyrics of "Pissin' on Your Steps", which appeared on his 1991 debut album I Wish My Brother George Was Here. Similar to 'Pop Goes the Weasel', the song negatively makes a connection between Van Winkle and Elvis, while saying Ice alongside MC Hammer are mocking hip hop by being commercial. Van Winkle responded to "Pop Goes the Weasel" with his 1992 song "The Wrath" and to many of his other critics by stating that they were simply jealous of his early success. He repeated a message to his critics on the Arsenio Hall show telling the critics who thought he would never make it that they could "kiss [his] white ass." In the intro on De La Soul's album De La Soul Is Dead, Ice's dance moves are complimented. In the 1992 song "Scenario" by A Tribe Called Quest, Phife Dawg expresses unbelievability over Ice's Platinum status. Vanilla Ice answered back in the song Hit 'em Hard.
While some business decisions with SBK hurt Van Winkle's reputation in the States, he continued to remain a very sought after personality in Europe. He was the first rapper to perform in China and the first Indian hip hop song, "Thanda Thanda Pani" (Cold Cold Water) by Baba Sehgal was inspired heavily by Vanilla Ice's music and style. New Line Cinema had written a role specially for Van Winkle in Freddy's Dead: The Final Nightmare, but scheduling conflicts with Van Winkle's To The Extreme Tour forced the role to be scrapped from the script. Michael Bay, who had directed Van Winkle in his music video for "I Love You", planned to have the rapper appear in a cameo in the 2007 film Transformers but Van Winkle was busy touring. Robert Van Winkle appears as a video game character in Championship Motocross released in 2001 on PlayStation 2. Limp Bizkit frontman Fred Durst stated "If it wasn't for Vanilla Ice, none of us white boys would be here today.". Former Ultimate Fighting Championship light heavyweight champion Chuck 'The Iceman' Lidell used Ice's song Too Cold for his entrance to the ring.
DJ Buzz Fuzz sampled Vanilla Ice's vocals from his 1988 song "Ice is Working It" for his song "The Intro Killer". Ice is Working It was also featured in the film Little Black Book. Rapper G-Child, best known for her appearance on ego trip's The (White) Rapper Show, has credited Van Winkle as being a major influence on her work. After meeting Van Winkle in 2000, G-Child performed freestyle raps at six of Van Winkle's performances, and opened for him four times. On a Halloween themed episode of SmackDown, John Cena dressed as Vanilla Ice performing a freestyle rap. Ice Ice Baby and Havin a Roni are featured in the video game DJ Hero. In 2011, Virginia Beach rappers Gates and HD released a single and music video named after Vanilla Ice.
Vanilla Ice has been referenced in various Hollywood films and television shows. In Austin Powers: International Man of Mystery, Vanilla Ice is seen frozen next to Powers in the cryogenic laboratory. Vince Vaughn's character in Be Cool was loosely based on Vanilla Ice, even parodying the urban myth that Ice was hung upside down over a hotel balcony. In the 2008 film Step Brothers, Adam Scott's character wins a high school talent show by dancing and lip syncing to "Ice Ice Baby". It was revealed in the seventh season of Friends that Chandler Bing was in first place in a Vanilla Ice lookalike contest while Ross Geller was in fourth place. Seth Green voiced Vanilla Ice in an episode of Robot Chicken, where the cast of Surreal Life go to Middle-earth from The Lord of the Rings where Ice is squashed by an Ent. In the season two premier of The Cleveland Show, Harder, Better, Faster, Browner, Kenny West (voiced by Kanye West) works at a rap-themed restaurant which features a mechanical Vanilla Ice as an attraction. In the last episode of season 4 of The Big Bang Theory, Raj sings "Ice Ice Baby". He was parodied on Saturday Night Live portrayed by Kevin Bacon where Chris Rock as Nathan X wonders how a white man dances so well. Jim Carrey parodied Vanilla Ice in one of his most known sketches on In Living Color, where Carrey dances and raps to White White, Maybe (a parody of "Ice Ice Baby") during the Extremely White Tour (parodying the To The Extreme Tour). Carrey dances again to "Ice Ice Baby" in the 2011 movie Mr. Popper's Penguins.
Eminem has often name-dropped Vanilla Ice in his songs. Starting during taped freestyles he did with rapper Proof in 1992 where they performed against each other portraying Ice and MC Hammer, respectively. In his first single "Just Don't Give a Fuck", Eminem mentions Ice alongside Everlast, boasting in a playful manner that he's a better rapper. In "Role Model", Eminem says he ripped out Vanilla Ice's dreadlocks. Van Winkle responded to in a magazine interview with Vibe saying that Eminem "raps like a girl". While Vanilla Ice and Eminem neither look at their responses as an actual beef, Eminem did reply to the quote in his song "Marshall Mathers" which also featured a verbal attack on the Insane Clown Posse. Eminem mentioned Ice again in the song "Purple Pills" in 2001, which caused Vanilla Ice's only response in song. On his album Bi-Polar, Ice mentions Eminem in a positive light ("Hip Hop Rules") and in a negative light ("Exhale"), however, Van Winkle stated that he has no bad feelings towards Eminem. In a 2002 interview, Vanilla Ice stated that he thought Eminem's references were flattering, going on to say "I give him credit, I think he’s talented, I think he’s a killer rapper, you know I don’t compare myself to him because he’s another white rapper, I don't compare myself to any other rapper period, I don’t colorize hip hop, it’s stupid, but for people who are doing that are just looking through the eyes of a racial standpoint, and it really shouldn’t be looked at that way, you’re looking at two musicians that are in a broad brand of hip hop, so you don’t need to compare us two. Following me, any white rapper is going to have to hear 'oh, you think you’re Vanilla Ice?', so I am sure he’s heard that."  In 2002, Eminem mentions Ice again on The Eminem Show and in the film 8 Mile. In the 2011 song Fast Lane, Eminem raps about riding in his car while listening to Ice Ice Baby.
In 2007, Nike released Vanilla Ice shoes for their
Fallen Heroes pack. In March 2009, Van Winkle participated in a
Virgin Mobile advertising campaign titled "Right Music Wrongs", apologizing for his 1990s image. As part of the campaign, Van Winkle was
placed on "trial", and was voted innocent by users of the campaign website. He also appeared
in a commercial for the South African light beer Castle Lite.
In 2010, Vanilla Ice was featured on the debut single of the Irish
duo John & Edward, a mashup of "Under Pressure" and "Ice Ice Baby". "Under Pressure (Ice Ice Baby)" was released in the United Kingdom on January 31, 2010 via download and as a
physical single on February 15, 2010. In 2010, Serbian musicians
Slađa Delibašić and Shwarz released the single and music video
Dizel Power. The music video and song feature various references
to Vanilla Ice, including the performers dancing next to a graffiti
mural of Ice.
DJ Dirty Chopstix — turntables and background
Earthquake (1987–2010) — turntables and background
Awards and Nominations
American Music Awards
People's Choice Awards
The Factual Entertainment Awards
Kemet & Maat
: before Judaism, Christianity and Islam