A video that I really like is Johnny Cash's version of "Hurt" (originally by Nine Inch Nails)
Here's a link to the video.
In it, Johnny Cash wears no makeup, and he really looks his age. There are shots of him in his younger days. The whole tone of the video gives a sense that death is right around the corner. And sure enough, he died not long after making this video. This video was nominated a bunch of times, and won a lot of awards.
I was never a big country music fan, but I will miss "The Man in Black".