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Born Gregory Skyler Taylor in 1982 in Crown Heights, he grew up in Bedford-Stuyvesant. He was nicknamed Skyzoo by his parents after the Skyy disco song (his middle name is Skyler). He began rapping at the age of nine and went on to work with producers Jay Dee and 9th Wonder, releasing several mixtapes in the hope of securing a record deal. He was beaten by Jin on BET's 106 & Park freestyle contest, but went on to have tracks used as both the theme to ESPN's Whiplash TV and the soundtrack to a Guinness advert, and set up his own Custom Made Entertainment company (Last.fm)