Years active: 1987 - present Hometown: Toronto, Ontario
When it comes to Canadian rappers, no list goes without mentioning Maestro. Often referred to as the Godfather of Canadian hip-hop, he was the first Canadian rapper to attain a Top 40 single with "Let Your Backbone Slide." Despite the fact that he had difficulty achieving the same level of success in the U.S., his debut record, Symphony in Effect, is still one of the best selling hip-hop albums of all time in Canada. In many ways, he paved the way and laid down the foundation for future Canadian hip-hop artists, as when he started out in '83, Canadian hip-hop was essentially non-existent. You can thank Drake later, but Drake can thank Maestro now.