“Ever since Waylon / I can’t find no one to buy into sad country songs”
—Jamey Johnson, “The Last Cowboy”

The popular image of Waylon Jennings is a rugged outlaw: bearded, with a black cowboy hat and leather vest. These reissues—of six albums released from 1966 to 1970—are an opportunity to listen to how he got there. They are a chance to view him first and foremost as a country singer: a singer of heartbreak ballads, a Singer of Sad Songs, as one of these albums is titled.

Each CD contains two reissued albums. The first CD, Folk Country (1966) and Waylon Sings Ol’ Harlan (1967), shows him in the thick of the Nashville sound of the time, with Chet Atkins producing. The fact that Jennings had a personal beef with the Nashville industry, one that became a major theme of his music in later years, doesn’t make the music he made for that industry any less brilliant. These two albums are both gorgeous and brutal. Listen to him sing, for example, “Stop the World (And Let Me Off)”. His voice, filled with seriousness, contains deeps reservoirs of sorrow. The songs vividly chronicle hurt and betrayal. He’s singing lyrics that sear, like “Look into my teardrops/and darling you will see/the reflection of an angel that made a fool of me”.

The best songs on both albums are now country standards, especially those penned by Harlan Howard, like every song on Waylon Sings Ol’ Harlan. Howard is rightly considered one of country music’s greatest songwriters ever. Jennings brings the dark vision of his songs to life. Most of the non-Howard songs on Folk Country, including several written by Jennings himself, fall into a similar category. Jennings sings about tragedy after tragedy, and makes the songs feel both intensely sober and personal. The traditional “I’m a Man of Constant Sorrow” (credited with Jennings as songwriter in the liner notes) is so convincing in Jennings’ hands, more so than even the popular, Grammy-winning Oh Brother, Where Art Thou version. Jennings sings Howard’s “What’s Left of Me” with a triumphant pessimism that plays up the song’s bitter humor while remaining a sort-of love song. The bitterness towards women that is one of the foundations of Jennings’ music is here (“Woman, Let Me Sing You a Song”). Already, Jennings has a way making vitriol seem triumphant and scary, a pure anger that you don’t dare touch.

Love of the Common People (1967) and Hangin’ On (1968) find Jennings in a similar vein, again with Atkins on board, but also show the way his music was being touched by the changing times. In short, he sings more contemporary pop/rock hits than before, songs like the Beatles’ “You’ve Got to Hide Your Love Away”, Roy Orbison’s “The Crowd” and Glen Campbell’s “Gentle on My Mind”. There are also more songs that touch on social issues, like the title track “Love of the Common People”. The sound seems a little more “rock ‘n’ roll” overall too, which isn’t necessarily to the albums’ benefit. Still, though these albums may not be as “pure” in that way, there are still some powerful black and white portraits in bleakness, like Ted Harris’ “The Road”, a harsh prison song, and Ben Peters’ “Two Streaks of Steel”, a leaving song, via train, that sketches the story out in quick strokes: “two streaks of steel I’ve been standing beside/where all that mattered in my life just died”. There are more cheating songs, like “If the Shoe Fits” (Howard again) and the immortal “Ruby, Don’t Take Your Love to Town”, which Mel Tillis wrote and Kenny Rogers popularized. The almighty bitterness towards women is back to, on Bobby Bare’s “Woman, Don’t You Ever Laugh At Me”. It’s also part of the toughest and most powerful song on either album, “The Chokin’ Kind”, written by Harlan Howard and later a hit for the R&B singer Joe Simon. Jennings is devastating, the way he intones the lines, “your love scares me to death girl/it’s the chokin’ kind”. That gets so powerfully at the fear that’s wrapped up so tightly within the heartbroken anger of Jennings’ music.

The last pair of albums, both from 1970, presents a statement of the direction Jennings’ music will be headed (Waylon) and an interesting departure that exists in its own category (Singer of Sad Songs). The cover of Waylon, an album mostly not produced with Atkins, is another iconic rebel photo. He’s not sporting a beard yet, but looks stern and cooler-than-cool, cigarette tight in his mouth. The album, his last before leaving Nashville for a Los Angeles sojourn, was cobbled together from previous sessions, but still comes off as a declaration of sorts. The text on its back cover proclaims “Waylon Jennings—Future Unlimited”. It begins on the highway, with Chuck Berry’s “Brown Eyed Handsome Man”, before running through more sad, haunted tales that carry a thick atmosphere of anxiety and pain, including more stories about the hurt women can do. Listen to the wail in his voice during “Don’t Play That Game”, as he sings, “every time that girl walks by/your heart will ache/your very soul will die”. Meanwhile, he decries the young women who throw themselves at him (“I May Never Pass This Way Again”), and shows some inner conflict in his lashing-out at the “Yellow Haired Woman” who is “good for nothing/empty-headed/most lovely creature I’ve seen”. 

Singer of Sad Songs, the first evidence of his Los Angeles period, has its fair share of cheating and drinking songs, plus 1960s covers (“If I Were a Carpenter”, “Honky Tonk Woman”). What distinguishes it from anything else Jennings did is Lee Hazlewood’s production style—crisp, full and lush—which meets Jennings’ no-nonsense approach in interesting ways. The album runs through a lot of the same sort of material as Jennings’ previous albums, but in a different way, and with some fresh detours. There’s the weird little interlude on Hazlewood’s “She Comes Running” and a rollicking version of George Jones’ “Ragged But Right”, a macho ego boost, rebel statement, and celebration of domesticity all at once. The album bears the huge stamp of Hazlewood across it, but never dampens Jennings’ mighty voice. Closing with Jennings and Hazlewood dueting on “Rock, Salt and Nails”, it’s a more obscure album than the others, making it perhaps the most coveted of the reissues. At the same time, it’s just one more piece of the Jennings’ puzzle, perhaps a minor one in the big scheme of things. Taken together, these reissues show the way that Jennings stood as a force of nature within the changing times. He changed over the years without really changing. Listening to these six albums now shines a spotlight on the depth of his talent and vision. He was so much more than a Nashville rebel.