Snow was born and raised in the North York district of Toronto, Ontario. For much of his childhood, he lived in the Allenbury Gardens public housing project, and at the age of 17 he moved to Ajax, Ontario. Growing up in a diverse neighbourhood, O'Brien blended dancehall and reggae with rock and popular music to create his own unique style of music. In 1988, Jamaican-born DJ Marvin Prince witnessed O'Brien deejaying at a party and the two quickly became friends. For the next few years, they practiced in Prince's basement with Snow providing vocals and Prince playing records. While on a trip to New York City, Prince mentioned Snow to rap star M.C. Shan. Shan then invited Snow to New York and introduced him to music producers, David Eng and Steve Salem. Snow eventually signed a contract to record on their Motorjam/Elektra record label and in 1993 released his debut album "12 Inches of Snow".