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25 Best Waylon Jennings Songs That You Should Be Streaming Right Now

25 Best Waylon Jennings Songs
by
  • Arden is a Senior Country Music Journalist for Country Thang Daily, specializing in classic hits and contemporary chart-toppers.
  • Prior to joining Country Thang Daily, Arden wrote for Billboard and People magazine, covering country music legends and emerging artists.
  • Arden holds a Bachelor of Arts in Journalism from the University of Tennessee, with a minor in Music Studies.

Though the country music legend died nearly two decades ago, Waylon Jennings songs still left an indelible mark on the genre. All through his career, he persisted in being a genuine and sincere artist, waging to record songs within him the way he desired to hear them.

Here are some of our favorite songs from the legendary outlaw.

1. “Only Daddy That’ll Walk The Line”

From: Only the Greatest (1968)

Having been a part of RCA Victor since 1965, this song written by Jimmy Bryant gave Jennings’ his biggest early hit – barely missing the top after it spent five weeks at No. 2 on Billboard’s Hot Country Songs. 

Waylon Jennings played other sounds and styles over the next five years, but this record served as an example for what would turn out to be his winning formula in the 1970s.

2. “This Time”

Nine years after his debut, Jennings struggled to get a Billboard No. 1 hit, but things changed when the country legend released his self-penned “This Time” – which is a stern warning to the woman she loves for her to keep in step.

3. “Luckenbach, Texas”

Though Jennings had never stepped foot on Luckenbach until 1997 – two decades after recording this mid-tempo ballad – it did not stop him from turning the song into a wistful, touching tribute to life’s simpler things.

Luckenbach, Texas” is also Jennings’ biggest hit on the Billboard, wherein it remained on the top spot for six weeks.

4. “Good Ol’ Boys” (Theme From ‘The Dukes of Hazzard’)

From ‘Music Man’ (1980)

Jennings did not only lend his voice to the television series The Dukes of Hazzard, but he also penned the theme song.

The track was released as a single, and it quickly hit the top spot on the Billboard Country Singles chart. 

5. “Amanda”

Written by Bob McDill, “Amanda” was originally recorded by Don Williams. Less than a year later, Jennings recorded the track for his 1974 album The Ramblin’ Man; however, Jennings did not release it as a single and only included it in his Greatest Hits album five years later.

6. “I’m A Ramblin’ Man”

Jennings finds himself telling his lover to move away from this rolling stone because she might only get hurt. With the song’s solid tempo and infectious guitar work, “I’m A Ramblin’ Man” became Jennings second No. 1 on the country chart.

7. “I’ve Always Been Crazy” 

From: I’ve Always Been Crazy (1978)

Jennings sang about how he was as a person – flaws and all – in “I’ve Always Been Crazy,” which became another country No. 1 hit for the legend. The song was a man’s truthful reflection for being frank about the whole thing but stopping short of expressing regret – after all, he’s proud of it.

8. “America”

From: Waylon’s Greatest Hits, Vol. 2 (1984)

In 1984, Jennings performed the song on a television special for the restoration of the Statue of Liberty. The publicity was a great factor for the single to peak at No. 6 on the Billboard country charts and was even nominated for Song of the Year. 

9. “Good Hearted Woman”

The “Good Hearted Woman” is one great example of Jennings being a classic outlaw.

10. “Are You Sure Hank Done It This Way”

Jennings paid tribute to Hank Williams Sr. ‘s influence in country music at the same time, questioning the genre’s trajectory with lines like “Lord, it’s the same old tune, fiddle, and guitar. So where do we take it from here?”

11. “Brown Eyed Handsome Man”

From: Waylon (1970)

The rock and roll song was originally written and recorded by Chuck Berry in 1956; Jennings covered it in 1970 and turned into another country hit.

12. “Can’t You See”

From: Are You Ready for the Country

Written by Toy Caldwell, the song was noted as being dark – with a man reflecting on his heartache.

13. “Rose in Paradise”

From: Hangin’ Tough (1987)

In 1987, Jennings earned his final No. 1 song through this mysterious track with lyrics about a man who killed his cheating wife and her lover.

14. “Mammas Don’t Let Your Babies Grow Up to Be Cowboys”

Guess we can all agree that there’s no one more than qualified than Jennings to caution expectant mothers against the lifestyle risks that come with rock and roll. Jennings started living the rough life of a cowboy in the late 1950s.

15. “Are You Ready for the Country”

Rather than addressing issues like racism, the track is more about general terror.

Other songs of Waylon Jennings that you need to check out:

16. “Wrong”

From: The Eagle (1990)

17. “Honky Tonk Heroes”

From: Honky Tonk Heroes (1973)

18. “Rainy Day Woman”

From: The Ramblin’ Man (1974)

19. “Sweet Dream Woman”

From: Good Hearted Woman (1972)

20. “Ain’t Living Long Like This”

From: What Goes Around Comes Around (1979)

21. “Dreaming My Dreams With You”

From: Dreaming My Dreams (1975)

22. “Lonesome, On’ry and Mean”

From: Lonesome, On’ry, and Mean (1973)

23. The Wurlitzer Prize (I Don’t Want to Get Over You)

From: Waylon & Willie (1977)

24. “Drinkin’ and Dreamin'”

From: Turn the Page (1985)

25. “Don’t You Think This Outlaw Bit’s Done Got Out of Hand”

From: I’ve Always Been Crazy (1978)

How about you? What are your favorite Waylon Jennings songs?

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