If anyone is a country parody singer, I think Brad Paisley might qualify - as highlighted below the comic. He writes perfectly country-styled songs, but his lyrical material is about guys whose wives leave them because they go fishing too much, and overweight nerds who live in their parents' basement and chat with girls on Myspace. He's got plenty of 'serious' material too, admittedly.
On the other hand, the only country song I've ever heard that matches the stereotype 'lost my dog, lost my truck, lost my wife' is by Toby Keith. So it's hard to tell.