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===Early career (1985β1989)=== In 1985, he was focusing all of his energy on motocross, winning three championships.<ref name="bein">{{cite news|url=http://www.miaminewtimes.com/music/video-how-vanilla-ice-learned-to-love-life-again-by-flipping-houses-8046351|title=How Vanilla Ice Learned to Love Life Again by Flipping Houses|last=Bein|first=Kat|date=November 16, 2015|work=Miami New Times|access-date=May 19, 2016|archive-date=March 6, 2016|archive-url=https://web.archive.org/web/20160306170737/http://www.miaminewtimes.com/music/video-how-vanilla-ice-learned-to-love-life-again-by-flipping-houses-8046351|url-status=live}}</ref> After breaking his ankle during a race, Ice 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. Ice used his beatboxing and breakdancing skills as a street performer with his friends at local malls during this time.<ref>{{cite web|url=http://www.roctober.com/roctober/greatness/vanilla.html|title=Vanilla Ice: The Ice Is Right|access-date=May 5, 2011|last=Austin|first=Jake|date=October 24, 1999|work=Roctober|archive-date=June 9, 2011|archive-url=https://web.archive.org/web/20110609192659/http://www.roctober.com/roctober/greatness/vanilla.html|url-status=live}}</ref> One evening he visited City Lights, a South Dallas nightclub, 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 City Lights manager John Bush if he wanted to perform regularly, which he accepted. Ice would be joined on stage by his disc jockeys D-Shay and Zero, as well as Earthquake, the local disc jockey at City Lights. The Vanilla Ice Posse or ''The V.I.P.'' would also perform with Ice on stage.<ref name="Vontz"/> As a performer for City Lights, Ice opened up for [[N.W.A]], [[Public Enemy (group)|Public Enemy]], [[The D.O.C.]], [[Tone LΕc]], [[2 Live Crew]], [[Paula Abdul]], [[Sinbad (entertainer)|Sinbad]] and [[MC Hammer]].<ref name="Vanilla Ice: Interviews">{{cite web|url=http://vanillaicecentral.com/jan302interview.html |archive-url=https://web.archive.org/web/20160308031423/http://vanillaicecentral.com/jan302interview.html |url-status=dead |archive-date=March 8, 2016 |title=Vanilla Ice: Interviews |publisher=Vanillaicecentral.com |date=January 3, 2002 |access-date=April 10, 2012 }}</ref> In January 1987, Ice was stabbed five times during a scuffle outside of City Lights. After spending ten days in the hospital, Ice signed a contract with the owner of City Lights, Tommy Quon, and his management company, Ultrax.<ref name="Newsmakers">{{cite book|editor=Mooney, Louise|title=Newsmakers: The People Behind Today's Headlines|edition=1991|publisher=Gale Group|isbn=0-8103-7344-0|page=[https://archive.org/details/newsmakerspeople0000unse_t8r6/page/442 442]|year=1991|url=https://archive.org/details/newsmakerspeople0000unse_t8r6/page/442}}</ref><ref name="Westfahl">{{cite book|last1=Westfahl|first1=Gary|title=Science Fiction, Children's Literature, and Popular Culture|year=2000|publisher=Greenwood Publishing Group|isbn=0-313-30847-0|page=[https://archive.org/details/sciencefictionch00west_0/page/100 100]|chapter=Legends of the Fall: Behind the Music|chapter-url=https://archive.org/details/sciencefictionch00west_0/page/100}}</ref> Two years later, Ice would open for [[EPMD]], [[Ice-T]], [[Stetsasonic]], and [[Sir Mix-A-Lot]] on the [[Stop the Violence Tour]].<ref name="Peisner">{{cite web|url=http://www.well-rounded.com/music/interviews/vanillaice.asp|title=Vanilla Ice: The Well Rounded Interview|access-date=February 13, 2009|last=Peisner|first=David|archive-url=https://web.archive.org/web/20020606031005/http://well-rounded.com/music/interviews/vanillaice.asp|archive-date=June 6, 2002 |year=1998|publisher=Well Rounded Entertainment}}</ref><ref name="deepcover">{{cite AV media | people = Vanilla Ice, [[Sway Calloway]] | title = Deep Cover: Vanilla Ice Explains What Really Happened w/ Suge Knight & Death Row Records Involvement | medium = Radio interview | publisher = SwaysUniverse.com | date = January 28, 2013 | url = https://www.youtube.com/watch?v=KE5sRXF34b4}}</ref> Quon saw commercial potential in Ice's rapping and dancing skills.<ref name="Mooney"/><ref name="McVea">{{cite news|first=Denise|last=McVea|title=The Hip-Hop Hustle|url=http://www.dallasobserver.com/1996-09-05/news/the-hip-hop-hustle/2|work=[[Dallas Observer]]|page=2|date=September 5, 1996|access-date=March 13, 2009|archive-date=April 17, 2009|archive-url=https://web.archive.org/web/20090417222004/http://www.dallasobserver.com/1996-09-05/news/the-hip-hop-hustle/2|url-status=dead}}</ref> Buying studio time with Quon's earnings from City Lights, they recorded songs that had been perfected on stage by Ice and his acquaintances with various producers, including [[Khayree]]. The two year production was distributed by an independent record company called [[Ichiban Records]] in 1989.<ref>{{cite web|url=http://www.avclub.com/articles/vanilla-ice,13518/|title=Interview with Vanilla Ice|access-date=March 10, 2009|last=Thompson|first=Stephen|date=May 6, 1998|work=[[The A.V. Club]]|archive-date=April 15, 2009|archive-url=https://web.archive.org/web/20090415142329/http://www.avclub.com/articles/vanilla-ice,13518/|url-status=dead}}</ref> "[[Play That Funky Music]]" was released as the album's first single, with "Ice Ice Baby" appearing as the [[A-side and B-side|B-side]].<ref name="Westfahl"/><ref name="Wartofsky">{{cite news|first=Alona|last=Wartofsky|title=The Iceman Returneth; Vanilla Ice: Once Hated, He's Back With a Different Rap|url=http://www.highbeam.com/doc/1P2-696609.html |archive-url=https://web.archive.org/web/20121023110920/http://www.highbeam.com/doc/1P2-696609.html |url-status=dead |archive-date=October 23, 2012 |newspaper=[[The Washington Post]] |date=November 22, 1998|access-date=February 13, 2009}}</ref> Tommy Quon personally sent out the single to various radio stations around the U.S., but the single was seldom played and when it was, it did not get the reaction Quon was hoping for. When disc jockey Darrell Jaye in [[Georgia (U.S. state)|Georgia]] played "Ice Ice Baby" instead of the single's A-side, the song gained a quick fanbase and other radio stations followed suit.<ref name="Westfahl"/> Quon financed $8,000 for the production of a music video for "Ice Ice Baby",<ref>{{cite news|first=Michael|last=Corcoran|title=Black and white & rap all over: Mass America moves to beat of hip-hop|url=http://nl.newsbank.com/nl-search/we/Archives?p_product=CSTB&p_theme=cstb&p_action=search&p_maxdocs=200&p_topdoc=1&p_text_direct-0=0EB3733140C43839&p_field_direct-0=document_id&p_perpage=10&p_sort=YMD_date:D&s_trackval=GooglePM|work=[[Chicago Sun-Times]]|date=January 27, 1991|access-date=February 26, 2009|archive-date=October 17, 2012|archive-url=https://web.archive.org/web/20121017140944/http://nl.newsbank.com/nl-search/we/Archives?p_product=CSTB&p_theme=cstb&p_action=search&p_maxdocs=200&p_topdoc=1&p_text_direct-0=0EB3733140C43839&p_field_direct-0=document_id&p_perpage=10&p_sort=YMD_date:D&s_trackval=GooglePM|url-status=live}}</ref><ref>{{cite news|first=Robert|last=Hilburn|title=Why Is Everyone Still Fussing About Ice?|url=https://www.latimes.com/archives/la-xpm-1991-03-17-ca-687-story.html|work=[[Los Angeles Times]]|date=March 17, 1991|access-date=May 26, 2019|archive-date=May 27, 2019|archive-url=https://web.archive.org/web/20190527050417/https://www.latimes.com/archives/la-xpm-1991-03-17-ca-687-story.html|url-status=live}}</ref> which received heavy airplay by [[The Box (US TV channel)|The Box]], increasing public interest in the song.<ref>{{cite book|last1=Banks|first1=Jack|title=Monopoly Television: MTV's Quest to Control the Music|url=https://archive.org/details/monopolytelevisi0000bank|url-access=registration|year=1996|publisher=Westview Press|isbn=0-8133-1821-1|page=[https://archive.org/details/monopolytelevisi0000bank/page/56 56]|chapter=Other Video Music Program Services}}</ref>
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