re: Who was the most popular outlaw country singer at the height of its popularity?

I've also heard it originated as a joke with a secretary at Tompall Glaser's studio who used tell those longhaired shaggy guys coming in and out of the studio that they looked like a bunch of outlaws. They ran with the joke and even put out an Outlaws record. with Willie, Waylon, Tompall, and Jesse Colter.