1. "Are You Sure Hank Done It This Way"
Of all the songs Jennings has written, none has galvanized country fans quite like this one, which looks at country's changing sound through the eyes of its revered patriarch, Hank Williams. Whether it's a positive or negative view is open to debate. One on hand, the opening verse states the "same old tune, fiddle and guitar" needs a change, and asks "where do we take it from here?" But by the time Jennings sings "tell me one more time just so I understand, are you sure Hank done it this way?" there's a clear sense of "you gotta be shitting me" in his query. Progressive-minded artists favor the more benign interpretation — Keith Urban once projected a clip of Jennings singing the opening verse on his tour's jumbo screens — while country purists use the titular question to take genre-bending artists to task. Either way, it's a damn fine bit of writing.