Waylon Jennings: 3 Outsiders Wax Poetic About Their Favorite Songs to Celebrate Waylon’s Birthday

by Jim Casey

Waylon Jennings was a grade-A badass. The icon became known as much for his rugged individuality as his music.

Stymied by the creative control of the producer-polished Nashville Sound era, Waylon Jennings broke free to spearhead the Outlaw movement of the 1970s. Waylon started making music the way he wanted to—with the band, studio, and producing of his choosing. It was unheard of at the time.

The result? Waylon’s albums became distinctive works of art: Honky Tonk Heroes, This Time, The Ramblin’ Man, Dreaming My Dreams, Lonesome, On’ry and Mean, and more. His songs became iconic: “I’m a Ramblin’ Man,” “Only Daddy That’ll Walk the Line,” “Luckenbach, Texas,” “Good Hearted Woman,” and more.

Waylon, 64, died on Feb. 12, 2002. On what would have been his 84th birthday on June 15, 2021, we tasked Outsider‘s Marty Smith, Wes Blankenship, and Jim Casey to wax poetic about their favorite songs from Waylon’s catalog.


Marty Smith, Outsider contributor

Picking just one Waylon song is hard as hell.

Waylon’s raspy baritone is distinctive and timeless, and fearlessly empowered many peers and fans by saying things they may not have had the strength to say for themselves. “Lord it’s the same old tune, fiddle and guitar / Where do we take it from here?” You can read Wes’ take on that classic below.

I’d go with “Highwayman,” but that’s not a Waylon solo track. It’s a super team of country music gods singing one of the most revered songs the genre has ever heard.

So I think I’ll go with “Amanda.” It cuts me to the soul. Waylon’s emotional delivery is so personal you’d swear he wrote every word about love lost. You feel every word. And after you listen to Waylon’s beautifully haunting effort, listen to Chris Stapleton and Morgane Stapleton’s version. Gracious sakes.

‘Are You Sure Hank Done It This Way’

Wes Blankenship, Outsider content producer

No genre of music calls out its generational shifts quite like country music. Those tectonic plates are in a perpetual state of lurching atop one another. The distinctive layer of pop sounds and glamour continually grind against the bedrock of “real country” created in another age.

Waylon Jennings speaks to this phenomenon in his own unique way, with a tip of the cap to Hank’s.

“Are You Sure Hank Done It This Way” is a stylistic and lyrical side-eye to the start of that pop country, Hollywood wave pool. It’s a creator standing in the eye of a hurricane. Waylon’s feet are firmly planted in his own identity as he laments the identity of his craft.

“Where do we take it from here?” His world is morphing before his eyes. It’s impossible to pick a favorite Waylon track, but I specifically enjoy this one because it has his iconic sound. It’s historically significant in country music’s grand scheme and pays reverence to country music’s most authentic artists, in a time when authenticity began to fade.

Hank woulda done it this way.

‘I’ve Always Been Crazy’

Jim Casey, Outsider senior editor

Waylon’s individualism was as clear as the cigarette that perpetually dangled from the corner of his mouth. And that’s the word I most closely associate with Waylon: individualism. Freedom of action over collective control.

We’ve all got the “crazy” in us. It’s nothing to be ashamed of. Waylon confidently croons it without a shred of remorse: “I’ve always been crazy, but it’s kept me from going insane.”

Waylon’s words remind me to celebrate—and balance out—my inner “crazy.”

The song also reminds me to celebrate the craziness of others. Like my singer/songwriter buddy, J.R. Ward, who has a tattoo of Waylon’s face on his left asscheek. Why? He’s a little bit crazy like the rest of us. But he balanced it out by getting Willie’s face on the right cheek. No remorse.