Years active: 1990s - present Hometown: Toronto, Ontario
Like many of the rappers featured on this list, D-Sisive began his rise to prominence during the '90s in the Toronto hip-hop scene. But what inspires him is slightly darker than that of his peers. Between 2001 and 2007, Derek Christoff took a six-year long hiatus due to his battle with depression, following the death of his mother in '01, and his father in '07. When he finally decided to make his return, D-Sisive came back triumphantly with The Book EP, which really gives listeners some insight as to how he was dealing with the death of his parents. It's this type of incredibly honest and personal narrative expressed through his rhymes, not to mention consistently stellar beats and poetic lyrics, that sets D-Sisive apart as one of the greats.