A native of Toronto, Offishall began his career in the city's mid-1990s underground hip hop scene, as a member of The Circle. He released several independent 12" singles, a debut album, and an EP, before signing with major label MCA Records in 2000. The following year, Offishall released his second album, Quest for Fire: Firestarter, Vol. 1, spawning the Billboard hit "BaKardi Slang", which popularized Toronto's nickname "T-dot", and the minor hit "Ol' Time Killin'"; both singles became his signature songs. After failing to release the Firestarter Vol. 2 album in 2003, on MCA, and later Geffen Records, Offishall briefly returned to the underground scene, releasing several more independent 12" singles.
In 2005, Offishall's third album, Fire and Glory, was released in Canada.
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