Omnivorous and engaging, Shad has a vision of alt-hip-hop that has won him legions of Canadian fans and a mantle's worth of awards. After winning a talent contest while completing his undergrad at Wilfrid Laurier University, the rapper used the proceeds to finance his debut, 2005's When This Is Over. A decade later, he was nominated for three straight Polaris Prizes, and snatched a 2011 Juno for Rap Recording of the Year out of the hands of contemporary Drake. Unafraid to tackle complicated questions about Canadian identity and systemic ills, Shad's thought-provoking work makes this playlist an exciting listen.