Love Ricky Skaggs, and that song is one of my favorites. If the history of country music interests you, there’s a fantastic multi-episode documentary on YouTube, BBC-produced, about the history of country music. It starts with The Original Carter Family and Jimmie Rodgers, goes through the Shania and Garth thing, and up to Gillian Welch and the people who are steering clear of Music Row in order to protect the integrity of their music. It’s a bit out of date on the end era, but the beginning and middle are fantastic, as BBC documentaries are traditionally when they don’t try to politicise them. It also touches on bluegrass ( I believe that “O Brother” was big when the documentary was made). It was cool to recall the era of the neo-traditionalists-Dwight Yoakum, Randy Travis, etc.
I'll have to watch this sometime, I've watched a number of other BBC4 documentaries on modern music.
http://www.youtube.com/playlist?list=PLICzuTNeb3tTbIIvm1389tY1VYwav-QrC
There was a great music documentary from the 70s (that traces the history of popular music, there are 17 episodes but the first one I think is just a sampler and not considered 'essential'). It's called "All You Need Is Love". I only see the (50s) rock and roll episode (vol 12) on youtube right now. The country episode is interesting.