The tragic and inspiring story of the leaders of Outlaw country and their influence on today's Alt-Country 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, Tyler Childers, 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, 21, 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 with Johnny Cash, Willie Nelson, and Kris Kristofferson, and later forming the Highwaymen, country's first supergroup, with them. The foursome battled addiction, record companies, ex-wives, tragic violence, and the I.R.S. and D.E.A., en route to unprecedented mainstream success. Today, their acolytes Jamey Johnson, Zach Bryan, Tyler Childers, Brandi Carlile, and Taylor Swift outsell all challengers, and country in its various forms is the most popular of all genres. In this fascinating new book, Brian Fairbanks draws a line from Buddy Holly through the Outlaw stars of the 60s and 70s, all the way to the country headliners and more diverse, up-and-coming Nashville rebels of today. He brings the reader deep into the worlds of not only Cash, Nelson, Kristofferson, Jennings, and Jessi Colter, but artists like Chris Stapleton, Sturgill Simpson, Ryan Bingham, and Jason Isbell, stadium-filling masters whose stories have not been told in book form, as well as new, diverse artists like the Highwomen, Brittney Spencer, and Allison Russell, and shows how a twenty-one-year-old bass playing plane crash survivor helped changed the course of American popular music.