I grew up listening to Kenny Rogers (more Pop Country, IMO) thanks to my grandfather. Still love to listen to that music: Gideon, Kenny, Daytime Friends and anything with Dottie West. So I'll carry the flag for The Gambler.
I don't listen to country but there's a few songs that I enjoy, Small Town Saturday Night by Hal Ketchum being one.
I'll throw in Eagles, before they made the lineup changes; the first few studio albums. The concept album "Desperado" is terrific, in my opinion:
http://www.youtube.com/watch?v=JY8ys03Mqmw&feature=related