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Frequently referred to as 'the Mount Rushmore of country music, The Highwaymen - Willie Nelson, Waylon Jennings, Johnny Cash and Kris Kristofferson - were American country music's first bona-fide supergroup. Between 1985 and 1995, when times were hard for country legends as country radio chased youth and the pop market, these four icons banded together, made three albums, and toured the world performing their greatest songs and the ones they'd recorded together while extending their mutual admiration for one another.

The film explores those years and the work they recorded together and features vintage performances, rare behind-the-scenes footage of life on the road and in the studio with producer Don Was, and new interviews with Nelson, Kristofferson, family members Jessi Colter (country singer and Jennings's wife), Annie Nelson, Lisa Kristofferson and John Carter Cash, band members Reggie Young (guitarist) of The Memphis Boys, Mickey Raphael (harmonica player) and Robby Turner (pedal steel guitarist) and managers Mark Rothbaum and Lou Robin.

The 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.