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 first in country music, with Johnny Cash, Willie Nelson, and Kris Kristofferson. The foursome battled addiction, record companies, ex-wives, violent fans, and the I.R.S. and D.E.A., en route to unprecedented mainstream success. Today, their acolytes Kacey Musgraves, Ryan Bingham, Sturgill Simpson, and Taylor Swift outsell all challengers, and country 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, bringing the reader deep into the worlds of not only Cash, Nelson, Kristofferson, and Jennings but artists like Chris Stapleton, Simpson, Bingham, and 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. Thought-provoking and meticulously researched, Willie, Waylon, and the Boys ultimately shows how a twenty-one-year-old bass-playing plane crash survivor helped changed the course of American music.