Waylon Jennings. Jerry Jeff Walker. Kris Kristofferson. Tompall Glaser. Listen to Outlaw Country on Spotify. Various Artists · Compilation · · 20 songs. Various Artists, Waylon Jennings, Willie Nelson, Johnny Cash - Outlaw Country - Music. Check out Outlaw Country by Various artists on Amazon Music. Stream ad-free or purchase CD's and MP3s now on While the locations and players change, what all these origin stories have in common is motivation: The outlaws wanted freedom. The singers. Various – The Very Best Of Outlaw Country Folk, World, & Country 5, Hank Williams Jr.–, All My Rowdy Friends Are Coming Over Tonight. NOW Outlaw Country CD. $ Waylon Jennings - Ladies Love Outlaws; Kris Kristofferson - Help Me Make It Through The Night All Rights Reserved.