Louis Riel, I guess... nobody outside of Manitoba seems to give a shit though...
Apparently the guy who inspired James Bond was William Stephenson and he was born here.
Oh, Terry Fox was born here, apparently. I didn't realise that. He's pretty famous in Canada, not sure elsewhere.
And we can also lay claim to Fred Penner yesssssssssss~~~~
I guess the most famous is Burton Cummings from The Guess Who.
Honestly Canadians in general don't tend to get very famous outside of Canada, and Winnipegers even more so... ;u;