Yep, agreed . I`ve always been Rock n Roll , but the progressive Outlaw music winds my clock also. Most of what is considered country nowadays is a far cry from it. Willie, Waylon and others put some fun and meaning back into it.
The Red Headed Stranger collection is awesome. Pancho And Lefty is great still today.
It`s not how they sing, but what they sing.

Yea, you could say Willie was in debt to the IRS. He never was good with , nor did he have, good management as far as business wise goes.
Hell, they even took the golf course.
What did he have to say about this? He said to hell with it. It wasn`t about the money to begin with. He also said that they would just write a few songs and hit the road and buy it all back.
If I remember correctly within eight months he had cleared over 2 mil.
It certainly don`t hurt to be from Texas to be a Willie fan. Even if you don`t like his music, ya gotta love the guy. He`s a living legend.