The tragic and inspiring story of the leaders of Outlaw country and their influence on today’s Alt-County and Americana superstars, tracing a path from Waylon Jennings’ survival on the Day the Music Died through to the Highwaymen and on to the current creative and commercial explosion of Chris Stapleton, Brandi Carlile, Zach Bryan, Jason Isbell, and the Highwomen.

On February 2, 1959, Waylon Jennings, bassist for his best friend, the rock star Buddy Holly, gave up his seat on a charter flight. Jennings joked that he hoped the plane, leaving without him, would crash. When it did, killing all aboard, on "the Day the Music Died," he was devastated and never fully recovered.

Jennings switched to playing country, creating the Outlaw movement and later forming the Highwaymen supergroup, the...

The tragic and inspiring story of the leaders of Outlaw country and their influence on today’s Alt-County and Americana superstars, tracing a path from Waylon Jennings’ survival on the Day the Music Died through to the Highwaymen and on to the current creative and commercial explosion of Chris Stapleton, Brandi Carlile, Zach Bryan, Jason Isbell, and the Highwomen.

On February 2, 1959, Waylon Jennings, bassist for his best friend, the rock star Buddy Holly, gave up his seat on a charter flight. Jennings joked that he hoped the plane, leaving without him, would crash. When it did, killing all aboard, on "the Day the Music Died," he was devastated and never fully recovered.

Jennings switched to playing country, creating the Outlaw movement and later forming the Highwaymen supergroup, the...