This film examines how their towering individual personas and mutual friendships meshed to form the group’s collective artistry, their success buttressed by the love and support they gave to each other. Each had achieved considerable success prior to 1985, at which time they began to strategize about working together to revitalize the country music scene and satisfy their own restless creativity. Nelson, Jennings, Cash and Kristofferson liberated American pop and country music from record label-and-producer control to create a new musical landscape where the artists controlled their songwriting, recording and performing. Performances from a previously unreleased concert film with the group recorded live at Nassau Coliseum in Uniondale, N.Y., in 1990, demonstrate the group’s chemistry and the power of their combined music catalog including “Highwayman,” “Sunday Morning Coming Down,” “Folsom Prison Blues,” “Mammas Don’t Let Your Babies Grow Up To Be Cowboys,” “Always On My Mind,” “Me and Bobby McGee,” “Desperados Waiting For A Train,” “Luckenbach, Texas,” “Silver Stallion” and more. ![]() ![]() Jennings and Cash add their perspective via archival interviews. ![]() Artists influenced by The Highwaymen, including John Mellencamp, Toby Keith, Marty Stuart, and Ray Benson of Asleep at the Wheel, are also interviewed.
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