Skinner’s Pond, P.E.I.’s favourite adoptive son spent his life crisscrossing the country with a six-string in his hand and spent his career telling the stories of the Canadians he met everywhere he went. But "Sudbury Saturday Night" wins first place here because back when he was just known simply as Tom Connors he got hired to play a Sudbury tavern called the Townehouse and wrote this song to entertain the crowd. They kept talking anyway, so Connors started stomping his cowboy boot on the stage to get their attention. And a legend was born.
Hip-hop has always been about hometown pride, ever since it first emerged in the Boogie Down Bronx. Early Canadian rap tried to crossover by covering over its northern roots. But not Kardi's ode to Toronto’s street language which also happened to popularize the city nickname, Tdot, and shot its video in hoods like Regent Park and Jane and Finch. Released in 2000, it was his first to crack the U.S. Billboard charts and to make Canada's top 40. It also single-handedly made it safe for Toronto rappers to rep the city that Drake would later redub The Six while putting the CN Tower on his album cover and name-checking locales like Weston Road, Queen Street and Fort York.
The late Inuk singer Kelly Fraser first broke out for her viral Inuktitut-language cover of Rihanna’s “Diamonds” in 2013. Three years later, the singer-songwriter from the small
Hudson Bay island of Sanikiluaq released this bilingual, politically charged track as part of the “No” campaign in a Nunavut referendum over allowing private land sales in the collectively structured territory. Her side won a resounding victory, and the powerful protest song later became the centerpiece of her Juno-nominated second album, Sedna
When I was a kid out in B.C. I lived near the railway tracks that hugged the coast. Now, in Toronto, I still live near tracks. Many, if not most, of us do. The railway stitched this enormous nation together and our greatest troubadour Gordon Lightfoot pays tribute in this classic folk song about the construction of "an iron road runnin' from the sea to the sea." For extra patriot points, it was commissioned by the CBC for a Jan 1, 1967 special commemorating Canada's centennial year.
