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Willie, Waylon and the Boys: the Ultimate Outlaw Country Primer

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Hear songs from Willie Nelson, Waylon Jennings, Kris Kristofferson, Johnny Cash and more, inspired by a new book.

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In 1985, four icons of outlaw country — from left, Willie Nelson, Kris Kristofferson, Waylon Jennings and Johnny Cash — formed the supergroup the Highwaymen.Mark Humphrey/Associated Press

Dear listeners,

I’m a sucker for anything remotely related to country music’s outlaw movement, and I recently tore through the audiobook of Brian Fairbanks’s tome “Willie, Waylon, and the Boys: How Nashville Outsiders Changed Country Music Forever,” an informative page-turner that inspired today’s playlist.

Coined in the 1970s to classify a certain kind of country music rebel, the term “outlaw” can be a little nebulous, and there’s endless debate about which artists were (and weren’t) a part of that club.* I appreciated Fairbanks’s decision, though, to focus primarily on the four artists who would form the country supergroup The Highwaymen: Texas’s braided sage Willie Nelson; the deep-voiced, country-rocking maverick Waylon Jennings; the legendary father figure Johnny Cash; and the Rhodes Scholar-turned-Nashville janitor-turned-songwriting superstar Kris Kristofferson.

In telling the stories of these four artists and the ways their careers intersected, Fairbanks also traces the larger arc of outlaw country — from its beginnings as a genuinely countercultural movement that flew in the face of the Nashville establishment, to its transformation into an empty marketing term, and its eventual rebirth in subsequent generations of freethinking country artists.

It’s difficult to distill the first wave of outlaw country down to just 10 tracks, but for this playlist, I gave it my best shot. You’ll hear songs from the aforementioned four, as well as tunes from Jessi Colter, Billy Joe Shaver and David Allan Coe. And as for those waves of outlaws who have recently revived the spirit of the Highwaymen? Stay tuned for a playlist dedicated to them in the coming weeks.

Almost busted in Laredo, but for reasons that I’d rather not disclose,

Lindsay

*Merle Haggard, for example, is sometimes grouped in with the outlaw movement. While the self-proclaimed Okie from Muskogee was the only one of the above mentioned artists to do significant jail time, there were other aspects of his career and philosophy that put him at odds with artists like Nelson, Cash and Kristofferson. Regardless of how you label him, Haggard is one of the greats — and worthy of a playlist all his own.

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