Waylon Jennings Songs Ranked

Waylon Arnold Jennings (June 15, 1937 – February 13, 2002) was an American singer, songwriter, and musician. He is best known as one of the founding pioneers of the Outlaw Movement. Jennings formed a rockabilly club band, The Waylors, which became the house band at “JD’s”, a club in Scottsdale, Arizona. He recorded for independent label Trend Records and A&M Records but did not achieve success until moving to RCA Victor, taking on Neil Reshen as a manager, who negotiated significantly better touring and recording contracts for him. He toured less after 1997 to spend more time with his family. Between 1999 and 2001, his appearances were limited by health problems. In 2001, he was inducted into the Country Music Hall of Fame. In 2007, he was posthumously awarded the Cliffie Stone Pioneer Award by the Academy of Country Music. Here are all Waylon Jennings songs. ranked.

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19. Lucille (Ol’ Waylon, 1977)

Waylon Jennings has got one of those voices that can make something out of nothing, but he made a concerted effort along with the likes of Willie Nelson and Kris Kristofferson to say something worth his voice and time, which a lot of Nashville singers were not bothering to do in the 1960s.”

18. Lonesome, On’ry and Mean (Lonesome, On’ry and Mean, 1973)

“Another Waylon masterpiece featuring the classic title track. Waylon is an absolute badass and this is the album that let the world know.”

17. Clyde (Music Man, 1980)

“Waylon had really perfected his sound by this time, not that some might find it a little Urban Cowboy-ish.  Despite the star-studded list of pickers on hand, you can still hear a great deal of Jennings’ own simple stuttered trademark playing all over this thing and, combined with his priceless voice, is all I need.”

16. America (Waylon’s Greatest Hits, Vol. 2, 1984)

“The lyric and delivery just knocked me out…especially the line about “the men who refused to fight”. I don’t think anyone could put it any better. The inclusiveness and out-there passion of this record make me proud to be an American and a Waylon fan”

See more: Waylon Jennings Albums Ranked

15. MacArthur Park (Country-Folk, 1969)

“This kind of music never goes out of style. The modern remakes really loose in comparison. Enjoy this song and learn what modern songs are based on.”

14. This Time (This Time, 1974)

“Pretty laid-back record from Waylon at the height of his powers. A quiet record, but not overwhelming with sadness or melancholy. Juts a good weekend hangout piece.”

13. Dreaming My Dreams With You (1975)

“Here he sounds pretty resigned and weary without losing the romance and troubadour spirit that was always at the heart of his music. You can actually imagine 50s pop stars like roy orbison or his old friend buddy holly singing the title track or ‘long time leaving'”

12. I Ain’t Living Long Like This (What Goes Around Comes Around, 1979)

“This, I think, is maybe the best song waylon performed. At least for me when I think of Waylon this is the song that pops into my head. Should say something negative or qualifying but cannot think of anything.”

11. The Taker (The Taker/Tulsa, 1971)

“This song was not an overly popular song for him and I have always wondered why. It showed his voice range and I always thought he put quite a bit of feeling into it. Another song I can listen to over and over again.”

10. Honky Tonk Heroes (Honky Tonk Heroes, 1973)

“This is a great old album which I remember from my younger days, but which I hadn’t heard in a very long time. Brought back some great memories!”

9. I’m a Ramblin’ Man (The Ramblin’ Man, 1974)

“This is easily one of my favorite of Waylon’s studio efforts from his ’70s peak. The man was very gifted at choosing the right songs to record.”

8. Just to Satisfy You (Just to Satisfy You, 1969)

“This song rocks along at a medium tempo and Waylon’s vocals are perfect for it. There’s enough minor key notes in it to keep my interest. I’d recommend this song to anyone who likes either country or rock and roll.”

7. Highwayman (The Highwaymen, 1985)

“This epic and haunting tune will spark your imagination and transport you to different places, personas, and different eras as each member sings a different verse. It is well-produced. The music supports the imagery, the vocals, and storylines, but it never indulges in annoying overproduction as some recordings do.”

See more: Kenny Chesney Albums Ranked

6. Theme from the Dukes of Hazzard (Good Ol’ Boys) (Music Man, 1980)

“If you were alive in the South during “The Dukes of Hazzard” heyday, then you know the theme song by heart. It’s classic Waylon, and it’s unforgettable!”

5. Only Daddy That’ll Walk the Line (Only the Greatest, 1968)

“This is a great old song from the past. He had great musicians in his band. This a fun well written song. I love anything Waylon or Willie sings. Great country music. Waylon rocks!”

4. Mamas Don’t Let Your Babies Grow Up to Be Cowboys (Waylon & Willie, 1978)

“I’m pretty much rock and roll to the core. But this is special, this song brings back a lot of memories of a time when life was more about having fun than being particularly responsible. There couldn’t have been a better combination Willie and Waylon for one of the best songs ever. Learn the words, sing along and you’ll end up smiling.”

3. Good Hearted Woman (Good Hearted Woman, 1972)

“Sure miss this guy and his real country style of singing. There are only a few of these real country singers left. Fantastic song. Oldie and a goodie!”

2. Luckenbach, Texas (Back to the Basics of Love) (Ol’ Waylon, 1977)

“A classic. We all need to give up our lifestyles of pursuing things and go back to the basics just like the lyrics say. Classic country at its best. Waylon Jennings rocks this vintage country tune. Love to listen to it in the morning it sets the mood for the rest of my day.”

1. Are You Sure Hank Done It This Way (Dreaming My Dreams, 1975)

“This song helps us to remember the country western singers from years ago. It also lets us remember the singers who have passed on and the two who are still with us. That they could all join together and make a great album.”