There's way too many Canadian country artists that have had trouble findin success in the US. It definitely is the songs that sound dated.

Paul Brandt is stuck in the 90's still. Boring kind of but all the Grandmas love him so he stil makes a decent enough living.

Deric Ruttan has done semi ok but he's buds with Dierks Bentley so he writes with him.

Johnny Reid is ehhh

Terri Clark stuck in the 90s.

I like George Canyon. He was on The Voice I think or another reality competition.
But even he is outdated.

Shania Twain is clearly the biggest name but even that's 90's.

I guess we're better at making annoying pop stars. Lol.