Well... it's pretty jank, to be frank. But of course it is! Jennings is a very talented songwriter, but if he was a professional animator I don't think he would be a very talented songwriter. But because he is, he gets to do fun things like animate his own videos. Speaking to Paste, he put it this way:
"I draw a lot but had never tried animating before. I had some of my drawings animated for me for a video a few years ago for the song 'Ain't No Friend Of Mine' but I really wanted to try the actual animation myself..."
It's not Jennings' first cartoon rodeo--he collaborated with a friend on the video behind "Ain't No Friend of Mine." See below for a more polished approach to the dang thing.
The song itself, "Rudy," finds Mr. Mason in a familiar little room, with hushed and grand guitar line, telling another child-like fable in his ho-hum, intimate, and inimitable way. Word to the wise: Paste's upload suffers from some frustrating compression undulations. Take a look for yourself over at Paste.