I'm sorry to be a downer on such a so-far positive thread...
I just came across this and watched the video for the first time. First off, in the interview, Willie only says he recorded the song, because it's "funny." Hardly a ringing sense of acceptance of gayness. Also, at the beginning of the video, it looks like Burt Reynolds and Willie Nelson are sitting there directing the video. Burt asks Willie what he thought of the take they just saw of men line dancing together. Willie replies, "Damnedest thing I've ever seen."
But I was horrified when, near the end of the video, there is a momentary image of one of the cowboys being dragged along the ground, away from the camera, by a small group of other cowboys. He's laying on the ground, trussed up with rope, his arms pinned along his side, being dragged feet first. Nothing funny there. It looks like what's happening is the exact thing that made Jack flee from the Jimbo bar. Anybody else perceive it that way?