Waylon Jennings was a pioneer of the outlaw country movement, but that doesn't mean he was completely bought into the idea ...

The Traveling Wilburys proved groups made up of music titans could roughly work. So country music took a second chance with The Highwaymen.

Waylon Jennings, Johnny Cash and Kris Kristofferson. “Highwayman” and the group’s platinum-selling debut album crossed over to the pop charts and anointed them as mainstream icons.

“Waylon was a dear friend, one of the very best of 35 years,” said Johnny Cash, who recorded and toured with Jennings, Willie Nelson and Kris Kristofferson as The Highwaymen. “I’ll miss ...