When it comes to country music duos, few can compare to the power of the pairing of Waylon Jennings and Willie Nelson. The two old friends and Outlaw Country originators recorded and performed ...

In the mid-1980s, an over-the-hill quartet called the Highwaymen stormed the country-music world. In the Nashville scene of the time, they looked like a bunch of grizzled dopers, which they were. For ...

Hear songs from Willie Nelson, Waylon Jennings, Kris Kristofferson, Johnny Cash and more, inspired by a new book. By Lindsay Zoladz I’m a sucker for anything remotely related to country music’s outlaw ...

Waylon Jennings and Willie Nelson go together like cold beer and a hot day. But not everyone was sold on the concept of a bona fide duo record between the two outlaw country legends. Both musicians ...

Willie Nelson saw Waylon Jennings perform at JD’s nightclub in Tempe in 1965 and was immediately impressed. Nelson and Jennings rebelled at Nashville's music restrictions, sparking the outlaw country ...

“I hope your damned bus freezes up again,” Buddy Holly told Waylon Jennings. “Well, I hope your ol’ plane crashes,” Jennings joked back. This playful exchange took place between famed 22-year-old rock ...