To be honest, he already is a pretty big star in the independent country western genre. I love all his stuff a lot, he recently tweeted about how he can hardly watch videos like the one you posted because he says his voice was too forced. He doesn't really sing like that anymore, check out his latest album, its super good, but its true his singing style has matured into what's natural for him which I think is the right thing, he has a fantastic voice, but like you I love his early stuff as much or possibly more. I love his low gravely voice he started his career with.
Here's a recent one, check it out.
He's from my home province where I live, which is cool as we don't have a lot of people like this from Saskatchewan make it.
https://m.youtube.com/watch?v=hh-jwdWmgxg