Undiscovered: 5 Waylon Jennings Songs We Know You'll Love

Happy Birthday to Waylon Jennings! With a career spanning over 50 years, we celebrate a life lived raucously. Jennings was part of a small group of artists in the 1970s and ‘80s (which included the likes of Willie Nelson and Kris Kristofferson) who fought for and won their creative freedom outside of the Nashville establishment that dictated the sound of country music. From this rebellion emerged the outlaw movement, a subgenre that continued to define Jennings’ decades-long career and musical legacy even after he died. Not only did he pioneer the movement, he made it popular. His style of singing still inspires today’s country singer-songwriters.

Sturgill Simpson, Hank Williams Jr, Eric Church, and Steve Earle have all credited him as a major influence in their own music. And if that wasn’t enough, the legacy of Waylon Jennings was permanently etched into the touchstone of Americana history when he was inducted into the Country Music Hall of Fame in 2001. In honor of his birthday, we want to honor his extensive body of work, his contributions to the American Songbook. However, because there are over 50 albums and collaborations in Jennings’ catalog, we’ve compiled a list of the ones you might not have heard before, but that we believe tell his story.

1. "Slow Rollin' Low"

This is actually a Billy Joe Shaver song that Jennings covered on his 1974 album This Time. Shaver’s lyricism and cowboy persona seemed to influence Jennings throughout his career. Shaver was actually a country outlaw singer himself, so Jennings recorded a whole album of his songs the year before called Honky Tonk Heroes.

2. "Desperados Waiting for a Train”

From 1985 to 1995, Jennings was part of a country supergroup called the Highwaymen, composed of three other icons of the outlaw genre: Johnny Cash, Kris Kristofferson, and Willie Nelson. They recorded three major label albums as The Highwaymen: two on Columbia Records and one for Liberty Records. “Desperados Waiting for a Train” is the sixth song off of their first record Highwayman. They pass the song back and forth, each singing a verse that narrates the end of an old man’s life, before harmonizing together on the chorus, lamenting the fact that this man is an outcast and an outlaw just waiting for death. It’s pretty dark, but a great song.

3. "Turn It All Around"

This tune is part of Jennings’ autobiographical 1987 album A Man Called Hoss, which chronicles Jennings' life story in ten "chapters," each of which corresponds to a single track. “Turn It All Around” is the penultimate chapter. Jennings reflects back on his past and sings hopefully about what is to come.

4. "Oklahoma Sunshine"

This is arguably the most underrated song off of Jennings’ most successful album, The Ramblin’ Man. It encompasses what made Waylon Jennings such a great musician. His voice has visceral power, and as a result, listeners can’t help but feel what he’s feeling when he sings. In “Oklahoma Sunshine”, his powerful, rough-edged tone only underscores the desire and despair of the lyrics: “I'd like to leave this God forsaken city but I can't go no matter how I try / But once again I'll be in Oklahoma tonight when I lay down and close my eyes / I'll be standing in that Oklahoma sunshine just got off a bus from another world."

5. "Outlaw Shit"

“Outlaw Shit” came out on Waylon Forever, Jennings’ posthumous record, on October 21, 2008. The backing band for this album is Waylon's son Shooter and his band, The .357's. His final recordings of unheard material are on this album. Much of this album was recorded in the mid to late 1990s but was forgotten about until about 2007. “Outlaw Shit” is a great send-off for the outlaw himself.

Do you like going to concerts? You can get $20 OFF your first order at SeatGeek! Use promo code: THENASHNEWS at checkout.

To hear more of country music’s best new releases, head to our Playlists Page and follow The Nash New Releases playlist on Spotify. For the latest country music news follow The Nash News on Instagram, Facebook, Twitter, and TikTok, and don’t miss our brand-new newsletter!

Please note that this article may have affiliate links or The Nash News may receive compensation. We are independently owned and the opinions expressed here are our own.