3 Heartbreaking Folk Songs by Waylon Jennings From His Pre-Outlaw Days

Waylon Jennings is most associated with outlaw country. But the country music subgenre didn’t reach its commercial peak until the 1970s. To understand how Jennings—along with Willie Nelson, Johnny Cash, Kris Kristofferson, and others—transformed the sound of country music, it’s important to look at how his career began.

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This list highlights Jennings’s early recordings, specifically the presence of folk songs in them. Yet even within the glossy productions he’d later discard, there was always an outlaw hiding in plain sight. Which makes sense considering how much the protest spirit has long defined the folk tradition.

Finally, there’s an additional thread between Jennings’s folk and country tunes: heartbreak. Let’s listen and find out how this outlaw tale began.

“Just For You” (1966)

With Folk-Country, Waylon Jennings began a historic collaboration with producer Chet Atkins. The relationship, though successful, was equally frustrating and eventually led to a mutiny against the country music establishment. In “Just For You”, Jennings offers loyalty to a romantic partner who continues to break his heart. However jilted he feels, the future outlaw promises to wait. “In spite of all the things you’ve said and done / I’m a fool, and you’re the only one,” he sings.

“Falling For You” (1966)

Written by Ralph Mooney, “Falling For You” finds Jennings, once again, in a hopeless relationship. “You’re a heartbreak in disguise / Yet I keep falling for you,” he tells his partner. The track appears on Leavin’ Town, which features the smooth production of the Nashville sound Atkins helped pioneer. The kind of pop veneer that led Jennings to rebel with his own country music subgenre. But before the outlaw era began, his laid-back croon was heard on early recordings like this that blended both country and folk.

“Don’t Think Twice, It’s All Right” (1964)

On his debut album, At JD’s, Jennings covers a Bob Dylan folk standard. Here, the narrator attempts to convince himself he’s already over a breakup. But it’s impossible not to notice the resentment: “You just kinda wasted my precious time.” You’ll also notice in the cover echoes of Dylan’s future shift toward country music—foreshadowing his duet with Johnny Cash on “Girl From The North Country” from Nashville Skyline. But here, Jennings reveals the kind of bitterness that might make any broken-hearted outlaw lonesome, on’ry, and mean.

It ain’t no use to sit and wonder why, babe
It don’t matter, anyhow
An’ it ain’t no use to sit and wonder why, babe
If you don’t know by now.

Photo by Michael Ochs Archives/Getty Images