10 Essential Waylon Jennings Songs

With a catalogue like Waylon Jennings', it's tough to pick just 10 songs! 

Written by Chuck Dauphin
10 Essential Waylon Jennings Songs
Waylon Jennings; Photo by Larry Hulst/Michael Ochs Archives/Getty Images

It’s hard to believe, but this week marks fifteen years since the passing of Waylon Jennings. With that in mind, we thought we would take a look at ten of his most seminal moments in the solo spotlight.

Note: We chose the solo hits because one could do such a list based on his collaborations with Willie Nelson, Johnny Cash, and wife Jessi Colter alone!

(Arranged chronologically)

1. “Only Daddy That’ll Walk The Line” – from Only the Greatest
Written by: Jimmy Bryant
The booming guitar and that rich voice were in full evidence from the beginning at RCA. Having been a part of the label since 1965, this Jimmy Bryant tune gave him his biggest early hit – narrowly missing the top after spending five weeks at No. 2. Jennings flirted with other sounds and styles over the next five years, but this rocker served as the prototype for what would become his winning formula in the 1970s.

2. “This Time” – from This Time
Written by: Waylon Jennings
Nowadays, if you went nine years without a Billboard No.1 hit, you would be off the label. However, RCA stuck it out with Jennings, and were rewarded with a slew of chart-toppers, with this 1974 Jennings composition being the first. A stern warning to his lover that she better toe the line, it was different style-wise and lyrically than much of what he had done prior, setting the stage for Jennings to become a bad-ass legend.

3. “I’m A Ramblin’ Man” – from The Ramblin’ Man
Written by: Ray Pennington
Sometimes, you need the right marriage of song and singer. Writer Ray Pennington recorded this song first, hitting the Top-30 in 1967, but Jennings turned up the guitar and the attitude with a song that might very well have been the best example of the “Outlaw” sound – at least for him as a solo artist.

4. “Dreaming My Dreams With You” – from Dreaming My Dreams
Written by: Allen Reynolds
While not his biggest chart single, ask most music experts and they will tell you that his Dreaming My Dreams album might very well have been his best. At the centerpiece of the disc was a tender ballad about a man wrestling with his emotions about a love gone wrong. Sandwiched in between much of his biggest up-tempo hits, this song showed what an effective vocalist Jennings was underneath the image.

5. “Are You Sure Hank Done It This Way” – from Dreaming My Dreams
Written by: Waylon Jennings
It should come as no surprise that Jennings wrote this lively number about a singer-songwriter questioning Nashville’s way of doing things. After all, he didn’t attend the CMA Awards, and was one of the first artists to gain creative control of his records. Four decades later, one can still see some of the similarities in the business and ask “Are You Sure Waylon Done It This Way?”

6. “I’ve Always Been Crazy” – from I’ve Always Been Crazy
Written by: Waylon Jennings
By the late 1970s, Jennings admittedly was tiring of the whole “Outlaw” image, though the sound of this one was much in that direction. However, the lyrics were a little more introspective, giving the singer one of his top chart hits. Maybe, as the song asserted, his craziness had kept him from going insane!

7. “Amanda” – from Greatest Hits
Written by: Bob McDill
Bob McDill’s revealing ballad about a man coming to terms with reaching middle-age had been around the block before, with Don Williams turning in a superb performance of the song in 1973. Six years later, Jennings shot to the top with this song which any man who has lived to see the other side of 40 has felt.

8. “The Theme Song From The Dukes Of Hazzard (Good Ol’ Boys)” – from Music Man
Written by: Waylon Jennings
The song that gave Jennings his only million-selling solo single will forever embed him in 1980s pop culture. In late 1978, the singer was asked to write the theme song for a CBS series about a moonshine family in the south. The series became The Dukes Of Hazzard, and Jennings’ rollicking theme provided not only a number one Country hit, but a No.21 pop showing – his biggest. And, his radio career proved to be useful for Jennings, as he spent seven years as the “Balladeer” (narrator) of the Friday night staple.

9. “America” – from Greatest Hits, Volume 2
Written by: Sammy Johns
Of his later solo works, this 1984 Sammy Johns song about pride in your country – though you might not totally agree with everything that it does – became one of his most remembered numbers. Having a large part to do with this was the video, which depicted the singer on the front porch of an old general store, and many other pictures of the U.S. of A.

10. “Rose In Paradise” – from Hangin’ Tough
Written by: Stewart Harris, Jim McBride
The song that gave Jennings his final run to the top was one of his most mysterious. Jim McBride and Stewart Harris’s lyrics about a man who kills his cheating wife and her lover were chilling, and Jennings took full advantage of each line. Easily the top song of his brief stint on MCA Nashville that reunited him with old friend Jimmy Bowen.

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