I guess I don't think of Justin as a man
Are Alanis and some of the other (musical-vacuum/borders-down) 90's acts the least generic of popular Canadian exports in the past 30 years? It's like the United States only wants polished exported versions of specific genres (Buble throwback standards, Bieber pretty-boy pop for teen girls, Bryan Adams pop-rock, Avril grrl-power pop, Shania pop-country). Another way of saying it is that the mainstream American media sometimes will give an odd-sounding native act a chance but rarely will be open to music from Canada that seems strange. That might have something to do with national record labels. Maybe Canadian record labels can be lazy in artist promotion because they'll be played in the homeland anyway? But meanwhile, all sorts of weird stuff comes over from the UK, with that country almost seen as a musical role model.
Errm, 18 pages in, first mention of Corey Hart, one of the most successful Canadians on the 1980's US pop charts and maybe the most underrated hit-making Canadian export of the past 30 years. Since the dawn of MTV, few men from anywhere have done pop at such a high level for a half-decade or longer.