[Waylon Jennings] is part of the vanguard that is said to be revolutionizing country music. Or at least making inroads by reinjecting the maverick element into a music that was populated to begin with by such maverick, unpredictable, and slightly unsavory spirits as Jimmie Rodgers, Bob Wills, and Hank Williams.
His songs present a picture of the raffish hero in love with the essential seediness of twentieth-century America, the unregenerate rebel who looks back with a mixture of pride and regret on all the loves he's lost and all the hell-raising fun he's had…. His landmark album, Honky Tonk Heroes, reflected the same hell-raising image. The defiant stance suits Waylon Jennings. You get the feeling that in another life he might have been a buccaneer. And yet you sense somehow that this is oversimplification. If there were no more to the self-described 'lovable losers and no-account boozers and honky tonk heroes' who make up Nashville's new breed, then what can account for their remarkable staying power, the perseverance that's kept them knocking around Nashville all these years just looking for a hearing for their music? And in the case of Waylon Jennings—sensitive, articulate, warm, and sardonic by turns—you look for the intelligence, the dedication, and the vulnerability that lie beneath the hard-bitten facade. (pp. 206-07)
The first thing that strikes you about the music of Waylon Jennings is its sincerity. Drawn from a surprising diversity of sources—Dylan, the Beatles, Chuck Berry, and rockabilly, as well as flat-out country—its one unifying factor has been Jennings's patent integrity, and like the work of … Johnny Cash, it depends for its effect more on force of personality than on strictly musical considerations. (p. 209)
There remain … uncharacteristic traces of self-consciousness even on his best recorded work, a stiff grandiosity of purpose that is very much at odds with the straightforward, plain-spoken stance of his in-person performance. Here the music is looser, more ragged, but somehow more exuberant and more right. And I think that if Waylon Jennings never made another record, the personal message that he manages to convey to anyone who goes to see him perform would be record enough, a strikingly intimate and vivid memory of the occasion….
[In live performances], the old songs don't come up that often; the emphasis is understandably on the more recent material…. Even so, there's room for many of the hits, from some of the earliest sides like 'The Only Daddy That'll Walk the Line' through the Kris Kristofferson period of 'The Taker' right up to the present day. It's a scrupulously careful winnowing of material. The songs exist side by side without quarrel or complaint, and presented in this way, each song reflecting a very personal vision from different stages of a lifetime, it is as if they are really just pieces of a larger work. (p. 213)
After a while the songs sound linked, not just thematically but melodically as well…. And each one is distinctively and recognizably Waylon Jennings; each song tells a different strand of a single story. A tale of pride and regret …, bitterness and nostalgia …, failure in love …, and beat resignation…. The songs look back with a weary kind of wisdom on a life that's still going on…. They're songs for aging cowboys. (pp. 213-14)
Peter Guralnick, "Waylon Jennings: The Pleasures of Life in a Hillbilly Band," in his Lost Highway: Journeys & Arrivals of American Musicians (copyright © 1979 by Peter Guralnick; reprinted by permission of David R. Godine, Publisher, Inc.), David R. Godine, 1979, pp. 204-16.