Jelleestone’s earliest performances were done with local Toronto rap groups PNP and ORB in the late 1990’s. Jelleestone signed a joint venture deal with Warner Brothers Records and his own Rex Entertainment Inc. in 2001. His first studio album, Jelleestone Thirteen, released in 2001 featured “Money Part 1,” which climbed the Billboard Hot 100 charts and saw international success. Jelleestone has toured and written with Canada’s top pop, rock, and soul artists, notably performing with Kardinal Offishall and Racalz. He was the executive producer of his second studio album, The Hood is Here, which he collaborated with 40 (Noah Shebib) to release. The Hood is Here features the single “Friendamine,” in collaboration with Nelly Furtado. Jelleestone has been nominated for song writers and radio awards, including Juno Award nominations for Best New Solo Artist, and Best Rap Recording in 2002. The Hood is Here also features a collaboration with ElephantMan, “Who Dat” which earned the MuchMusic Video Award for Best Rap Video in 2004.