OK, I'll accept that George Jones owns the #1 saddest/most depressing country song of all time.
But this one has got to be first runner-up:
Edit: After I'd posted this, I checked to confirm that that was Ricky Schroeder. Sure enough, and he also directed the video. I also learned that he is a member of the NRA, a Republican, and a member of the Church of Jesus Christ of Latter Day Saints.