An insulting question led Waylon Jennings to humorously threaten a British reporter during a 1991 interview with The Highwaymen.

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 ...