"Plot" Summary: The video is a poignant acting-out of the lyrics - the story of a girl who falls for the "bad boy" only to discover that bad boys don't stick around for the long haul.
Of note: the role of the eponymous "Walkaway Joe" was played by Matthew McConaughey in one of his first high-visibility acting jobs.
Since the song is Trisha Yearwood's and Don is simply a guest, he doesn't get much face time. When he is shown, he is standing catty-corner and to the rear of Trisha Yearwood, looking away from her. I find their placement, which isolates them even though they are standing within feet of each other, a very interesting directoral choice. I love the visual nuances such as Don's shadow being visible even when the camera has zoomed in on Trisha and he is out of frame. Their set is in color, whereas the "story" with Matthew McConaughey is in black and white.
Don's expression doesn't really change throughout, but he has a world-weary look in those blue eyes as he harmonizes on this tale of learning life lessons the hard way. "He's the wrong kind of paradise... she's gonna find out in a matter of time..."
But hey, a romp with Matthew McConaughey might fall under the "favorite mistake" category when it comes to life lessons!