YouTube - Cool Runnings Theatrical Trailer (1993)
CTV, Canada’s official Olympic station, will be airing this movie this week because, as you may remember, it was in Calgary in 1988 where the Jamaican bobsled team debuted. CBC used to play this movie a lot. I think, set half in Canada, starring John Candy as the gruff but good coach, and with jokes about how cold snow is, Cool Runnings qualifies pretty easily as Canadian content.
ETA: Unfortunately, Jamaica failed to qualify for the 2010 Olympics, but Ghana has a skier, Kwame Nkrumah-Acheampong, headed to Vancouver.