Outlaws and good old boys Jennings and Cash had worked together previously and had great respect for each other; Jennings was a good friend of Cash's, the latter calling him his "blood brother". The two would go on to release a collaborative effort entitled Heroes in 1986. Cash had also arguably jumpstarted Kristofferson's career by promoting him and one of his most well-known songs, "Sunday Mornin' Comin' Down", famously covering the latter. Nelson had also worked with Jennings on three previous albums: 1978's Waylon and Willie, 1982's WWII and 1983's Take It to the Limit, and with Kristofferson on the 1982 album The Winning Hand with Dolly Parton and Brenda Lee. Though Cash and Nelson hadn't had much contact prior to the group's formation, there was mutual respect between them; notably, they would release the live VH1 Storytellers album together in 1998. While Kris Kristofferson was perhaps lesser known for his participation in the outlaw country movement popularized by Nelson and Jennings, he was prominent on the Austin music scene during its 1970s heyday and included in the Highwaymen as a mark of his musical collaborations with and contributions to the others in the group.