When it comes to hits and iconic songs, few can match the career highlight reel of Waylon Jennings. Armed with a large baritone vocal that’d quiet a room as quickly as it could rile one up, Jennings’ catalog of songs is as diverse as they come. There’s a rowdy anthem or slow ballad for any and every emotion. As essential as Jennings is the to the American songbook, it’s understandable that even some of his best work can slip through the cracks.
With over 50 studio albums and collaborations in his arsenal, it can feel intimidating sifting through the 50-plus years of material. Still, it’s as rewarding as one can expect. For every “Only Daddy That’ll Walk the Line” or “Are You Sure Hank Done It This Way?” there’s a plethora of material that’s just as good.
Like so many legends, Jennings is an iceberg. There’s an underbelly of material that makes up the body of his life’s work. You love and appreciate the known entities, the top charting hits and energetic ramblers, but it’s the songs that make up the lower half of an artists’ discography that truly makes them legendary.
15. “Slow Rollin’ Low”
Though Jennings had recorded Honky Tonk Heroes just a year before, an album consisting of nearly all Billy Joe Shaver songs, he’d only record one more Shaver song for the rest of his career. Like those on Honky Tonk Heroes, “Slow Rollin’ Low” is both vintage Jennings and Shaver. The laidback swagger of Jennings delivering is only matched by Shaver’s crusty cowboy lyricism.
14. “Suddenly Single”
For most, Jennings had lost his outlaw edge during the ’80s. Years of hard living, becoming 40 and growing tired of the outlaw bit in general, had caught up to Jennings. Even so, Jennings still could deliver a lonesome and sad ballad with the best of them. “Suddenly Single,” found on ’85’s Will the Wolf Survive?, at times feels dated with its’ synthesizer brushstrokes. Still, Jennings’ vocals are as heartfelt as ever.
13. “Love of the Common People”
“Love of the Common People” was the title track for Jennings’ ’67 album. Produced by the legendary Chet Atkins, the production is as light and airy as Jennings ever really got. The horn section and harmony vocals add smooth accents. Starting off slow, “Love of the Common People” never sinks back down, but rather, continues reaching for a space progressively higher.
12. “Nowhere Road”
Originally written by Steve Earle and Reno King, this version of “Nowhere Road” was a bonus track on the iconic Wanted! The Outlaws 20th Anniversary reissue. It finds Jennings in his prime with long-time collaborator and friend, Willie Nelson. “Nowhere Road” shows that even on celebrated albums like Wanted!, there are gems to be found.
11. “Old Church Hymns and Nursery Rhymes”
Found on ’90’s The Eagle, “Old Church Hymns and Nursery Rhymes” is another soft and pensive moment for Jennings. He’s nostalgic for a time that’s even before his own, but rather than sounding melancholy (or even pessimistic) like he typically would, he sounds deep in thought and solemn.
10. “It’s the World’s Gone Crazy (Cotillion)”
Written by Jennings and Shel Silverstein, “It’s the World’s Gone Crazy (Cotillion)” feels like a tongue-in-cheek response to his previous album, I’ve Always Been Crazy. It’s charming, laidback and almost sounds like a throwaway tune between two friends seeing just what they could get away with. They say there’s truth in every joke so lines like “Side men all want to be front men and the front men all want to go home” aren’t just funny, but as real as anything by Jennings.
9. “Slow Movin’ Outlaw”
Another song from ’74’s This Time, “Slow Movin’ Outlaw” finds a reminiscing Jennings. Even when so much of the Outlaw Movement was based on bravado, hard drinking and even harder living, an integral part was about a world closing in on outsiders and old souls. Time and again, Jennings captured the nostalgic longing for when the frontier was still the frontier and times were simpler. “Slow Movin’ Outlaw” is yet again, another prime example.
8. “Whistlers and Jugglers”
“You take the lady, I’ll take the lesson” may be the saddest opening line found on a Jennings tune. Written by Silverstein, it’s quite the turn from Silverstein’s usual comedic material — like “It’s the World’s Gone Crazy (Cotillion)” for example. It’s as broken a heartbroken love song as you’ll find in the Jennings catalog.
7. “Iron Road”
In hindsight, the Jennings and The Old 97’s collaboration makes perfect sense. They feel like kindred spirits. Though brief, they’re speaking the same language. Even though released in 2013, the collaborative efforts were originally recorded in 1996. The jangling rhythm of “Iron Road” is prime Old 97’s. Jennings sings the Murray Hammond original as if he’s been reinvigorated with life.
6. “Willie and Laura Mae Jones”
Originally written by Tony Joe White, it’s easy to see why “Willie and Laura Mae Jones” is right in Jennings’ wheelhouse. Like so many songs written by others, Jennings finds the space the writer was in when originally written. He channels that emotion, becoming the character for those moments.
5. “Chapter Nine – Reflections “Turn It All Around”
Overall, A Man Called Hoss is as underrated as it gets in the Jennings catalog. Divided into chapters, A Man Called Hoss is as autobiographical as it gets for Jennings. As hinted in the title, “Turn It All Around,” Jennings is reflecting. You can hear the optimism in his voice. He’s found a sense of peace after years of searching.
4. “Oklahoma Sunshine”
Found on The Ramblin’ Man, “Oklahoma Sunshine” is nestled on perhaps Jennings’ best album. Had it been recorded for another album, it’d have probably made its’ way as a single on the radio. Even in midst of the Outlaw Movement, Jennings rendition of “Oklahoma Sunshine” is already hinting at growing tired of it all and searching for a life that’s a little slower and uncomplicated.
3. “Them Old Love Songs”
“Them Old Love Songs” is as simple and straightforward as it gets. The slow-burning tune was written by Donnie Fritts and Troy Seals. Jennings sings lines like “Wish I had me a true fine woman, let her rock me all night long” that balances dejected loneliness with a confident strut that only a vocalist like Jennings could deliver.
2. “Frisco Depot”
Mickey Newbury, an underrated artist in his own right, wrote the lonesome “Frisco Depot.” Jennings recorded the sad and sinking ballad for his ’72 album, Ladies Love Outlaws. Jennings delivers lines like “When you’re alone there’s nothing as slow as passing time” with a conviction seldom matched.
1. “Outlaw Sh*t”
Though every Jennings fan should be familiar with “Don’t You Think This Outlaw Bit’s Done Got Out of Hand,” it’s understandable if they’re not with 2008’s rendition, “Outlaw Sh*t.” What ultimately became Waylon Forever was recorded by a teenage Shooter Jennings with his father. Deep down, “Outlaw Sh*t” has Jennings with one foot firmly rooted in the past while the other is pushing forward into the unknown future. It’s as sobering and solemn as anything in Jennings’ catalog. It’s as heartbreaking and satisfying as anything found on Johnny Cash‘s American Recordings.