I first got to know Canadian singer, k.d. lang's, country music, but she also can sing pop and jazz. A four time Grammy winner, her most recent win was for A Wonderful World, an album of duets with Tony Bennett which features songs sung by Louis Armstrong.
"Big Boned Gal," from her album, Absolute Torch and Twang, is one of the first songs I heard of hers (the video ends up stretched out side to side - if you want to see it normally, click here).
Unfortunately, country will be one of my smaller categories. I enjoyed country music in the 90's when it seemed to open up a bit and add some variety. Since then, it's changed, and now country often seems to be 70's pop with a twang and a hat.
In the 90's, though, I started listening to some good country singers such as Kathy Mattea, Mary-Chapin Carpenter, Suzy Bogguss, Wynonna, and The Tractors. I still keep up with their music, and I occasionally tune into a country station to see if I find something interesting.
In 1992, Suzy Bogguss had her first top 10 country hit with Nanci Griffith's "Outbound Plane" (from her CD, Aces).
Here's a video (rather long) with Nanci Griffith singing "Ford Econoline," then a discussion between the two of them, and then the two of them singing "Outbound Plane" (skip to 6 min 45 seconds to just hear "Outbound Plane").