In 1991, while on tour in New Zealand, country music icons Kris Kristofferson, Johnny Cash, Willie Nelson, and Waylon Jennings—also known as The Highwaymen—took a break from the stage to discuss the pressing issues they felt were shaping America at the time. These legendary outlaws shared their candid thoughts on the country’s biggest challenges and what they believed the nation had gotten wrong. Their conversation touched on everything from social justice to political missteps, offering a rare glimpse into the personal views of four artists whose music and activism often mirrored the struggles of their time.