Willie, Waylon, and the Boys

How Nashville Outsiders Changed Country Music Forever


By Brian Fairbanks

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$41.00 CAD

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.

  • “Best New Books in June (2024)” –The Independent
  • “[A] his no-holds-barred chronicle of the compadres: Willie Nelson, Waylon Jennings, Johnny Cash and Kris Kristofferson...[Fairbanks] revels in the eccentricities as well as the peccadilloes of this band of outsiders.”
    Wall Street Journal
  • “Fascinating… Fairbanks’ compelling stories bring the reader deep into the worlds of not only Cash, Nelson, Kristofferson, and Jennings but contemporary artists like Chris Stapleton and Jason Isbell.”
    OUT ALL DAY: New Orleans
  • “The writing is well done – there’s a lot of facts and a lot of quotes, but it never really feels like dense academic oriented text or a philosophical treatise… Very much recommended.”
  • “An interesting study of the vaunted outlaws of country music, who turn out to be reasonably law-abiding citizens… A pleasure for fans of the smoke-shrouded, hell-raising men in black—and tie-dye.”
  • “Enthusiastic… a diverting look at how a noteworthy strain of country music came to be.”
    Publishers Weekly
  • "Fairbanks keeps the story moving, deftly changing from one musician to another throughout the book. This volume sings on each page and is suited to any library’s music history section."
    Library Journal
  • "Bursting with fascinating stories from the annals of country music history..."
    Nashville Scene

On Sale
Jun 4, 2024
Page Count
464 pages
Hachette Books

Brian Fairbanks

About the Author

Brian Fairbanks was an investigative reporter at Gawker and the Consumerist. He has also written for the Guardian, Business Insider, the New York Observer, Nerve, and many more outlets, and is the author of Wizards: David Duke, America's Wildest Election, and the Rise of the Far Right.


Learn more about this author