CMT Presents the Highwaymen is a 2006 release, also called American Revolutions: The Highwaymen, and finds the country music supergroup at work on their third and final CD together.
They were quite a team: Waylon Jennings, Johnny Cash, Willie Nelson, and Kris Kristofferson, a quartet of what singer-songwriter Rodney Crowell, Cash's erstwhile son-in-law, calls 'poets, poker players, and madmen.'
But having been at the forefront of what used to be known as the outlaw country movement, they were also unconventional guys who realized that there was a significant audience for their music somewhere at the confluence of hippies and cowboys.
The documentary includes some old footage of all four musicians, but the bulk of it, recorded in 1994, finds them hashing over the past (including their differences - seems Waylon and Kris weren't exactly on the same page, politically speaking), preparing new songs with producer Don Was, and at work in the studio. Archival footage of their meeting with Gene Autry is included and interviews with the likes of Jessi Colter, Shooter Jennings and Billy Joe Shaver.
The 45-minute programme is supplemented by an additional half an hour of interviews.