I generally consider the well groomed image of any “entertainer“ to be a veneer about as thick as that silvery layer on a scratch off ticket, and about as tough too.
Outlaw country? GTFO with that. The only thing outlaw about “outlaw country” is that it didn’t conform to what radio program managers wanted to play. “Outlaw country” was an inside joke that got picked up and carried. Now, as a modern genre of music, “outlaw country” beats the shit out of Hick Hop and bruh country and whatever the shit you call the drivel coming out of Sam Hunt’s mouth. Outlaws? They‘re singers, not street fighters. They’re more likely to engage in a dance-off then get caught up in a bar fight...
Well.. Willie always been a pussy ass hippy masquerading as a country singer. Apparently Cash was a pussy ass liberal too. But there was a time in Waylon’s life when he was running with legit badass biker gangs, plowing oz’s of coke a night, and generally raising hell off stage and on... Qualifies him to have the title “outlaw” as much as any IMO.
What did you expect of them to do? Serve in the Confederate Army, and carry on the “lost cause” as bank robbers, train robbers, etc with Colt cartridge conversions, Schofields, and assorted muzzle loaders, breech loaders, and lever actions while on horseback? And kill any Pinkerton that comes after em ala the ORIGINAL ACTUAL outlaws, the James-Younger gang. All this in between their frequent concerts of course.
Or maybe in between concerts, rob some trains on horseback with a .45 SAA and a Winchester, kill a few in the process, then run on down to Bolivia when things get too hot, set up a cattle ranch there(with weekly concerts
) ala Butch Cassidy? And ultimately get surrounded and shot to pieces by a battalion from the nearest Bolivian Army base.
Would you consider em outlaw enough then?
Let’s be realistic. You simply can’t be a TRUE “outlaw” and a “celebrity” simultaneously, without ending up with a major prison sentence or murdered by some rival/authorities.
But Waylon Jennings came as close as any to EARNING the title of outlaw, all the while still keeping every bit of his respect, dignity, and honor, unlike the likes of Coe(a true snake) who’d sell his fathers MoH(if it existed) for a decent size chunk of crack.