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Snort a Double Dose of Waylon Jennings with a New Highwaymen Documentary and Book of Road Stories

Check out an exclusive peek at the Highwaymen's new American Masters documentary, and our thoughts on the new book from Waylon's son (and partner-in-crime), Terry.

by Kim Kelly
16 May 2016, 5:39pm

It's a good time to be a Waylon Jennings fan. Those of us who've been missing the ultimate country music outlaw and dearly departed ramblin' man will soon be positively swimming in never-before-read stories and rare recordings from one of his most iconic projects

Not only has the ultimate country music insider—Waylon's own son and longtime roadie, Terry Jennings—released a new book about his father's on-the-road exploits, but Watasha's first supergroup, The Highwaymen, is getting a plush reissue treatment from Columbia/Legacy. The Highwaymen Live—American Outlaws is a three CD set of live recordings from the band's heyday (plus a DVD's worth of previously unreleased concert footage from their 1990 Nassau Coliseum show), and also features an previously unreleased version of their cover of Bob Dylan's "One Too Many Mornings. The collection is out May 20, and dovetails with a new PBS documentary.

The band (which famously paired Jennings with fellow country giants Johnny Cash, Willie Nelson, and Kris Krisofferson) is the subject of a new American Masters episode that follows the story of four country giants as they came together to conquer the music world anew. If you liked what they did with Loretta Lynn's story, you're going to want to tune in on May 27 to catch American Masters—The Highwaymen: Friends Till the End.

Check out an exclusive clip below to find out how Jennings and Willie Nelson launched the outlaw country movement, and liberated artists from record label-and-producer control:



If you're more of a reader than a TV person, you can still get your Waylon fix. Waylon: Tales of My Outlaw Dad came hot off the presses from Hatchette Books earlier this year, and is billed as a warts 'n' all account of Jennings the Younger's thirteen years on tour with his hellraising daddy working as a drum tech, roadie, and partner-in-crime.

There are plenty of sex and drugs (including a PCP-heroin combo called Atlanta Dog that sounded absolutely terrifying) , but the parts of the book that most stuck out to me, as a fan and as someone who's no stranger to life on the road, were the quieter moments. The author makes no bones about the complex nature of his relationship with his father—when they were on the road, "Dad" felt too familiar and "Waylon" too distant, so Terry settled on calling him "the Ol' Man"—but his love and respect for the man shines through the simple prose.

The best stories are the ones that focused on little things, like finding out that Waylon got the idea or his iconic "W" logo from a Gene Autry film, or that he liked to mess with his crew by sneaking into their bathrooms and going wild with the Super Glue, or that he was friends with Muhammad Ali, or that Johnny Cash, playing, amateur photographer, had snapped family portraits of Waylon and his kin on a group trip to Jamaica.


The author doesn't pull any punches on his own misbehavior, either, and while his writing is more functional than lyrical, Waylon: Tales of My Outlaw Dad is a quick, fun read that offers the reader an intimate look inside a world that doesn't exist anymore—which is probably for the best, because it's hard to imagine any modern musician being half as tough or living nearly as wild as the Ol' Man and living to tell about it!

Kim Kelly is lonesome, orn'ry, and mean on Twitter.