The 8 Best Waylon Jennings Songs, Ranked


Waylon Jennings is a country music icon. His first band was The Texas Longhorns, after all. Instrumental in paving the way for the outlaw country movement in the 1970s, Jennings collaborated with some of Nashville's greatest talents during his lifetime. 

Wanted! The Outlaws was released in 1976 featuring Willie Nelson, Tompall Glaser, and Jennings' wife Jessi Colter. The album became the first-ever platinum country album. He released three albums with the country supergroup, The Highwaymen, which also included Willie Nelson, Kris Kristofferson, and Johnny Cash. He was inducted into the Country Music Hall of Fame in 2001 (one year before his death) and posthumously honored with the Cliffie Stone Pioneer Award. The man even passed along his talented country singing genes to his son, Shooter Jennings, who is also active in the outlaw country scene.

We've rounded up eight of the best Waylon Jennings songs to remember the legend that he was and the vital role he played in country music over the years.

8. "Only Daddy That'll Walk the Line"

Country singer Jim Alley first recorded this song but Jennings made the song famous when he released it on his album, Only the Greatest in 1968. Hank Williams Jr. also covered the song.

7. "Rose in Paradise"

This song was the twelfth number one country single for Jennings. Written by Stewart Harris and Jim McBride, the song tells the story of a woman named Rose who marries a rich banker that turns out to be a possessive man who keeps her locked away. He hires a gardener to keep an eye on Rose when he leaves town, and she ends up mysteriously disappearing.  

6. "I'm a Ramblin' Man"

This song warning listeners to beware of ramblers hit number one on the country charts for a week in 1967. The title track from Jennings 1974 album that also gave us the number one hit, "Amanda." Jennings was a busy guy, he also released This Time that year. 

5. "I've Always Been Crazy"

This song was Jennings sixth number one as a solo artist, released on the album with the same name. The album was one of his greatest hits, hitting number one across the board in addition to a number one duet album with Willie Nelson. Along with the title track, Jennings had ten more top 10 singles on I've Always Been Crazy.

Read More: 10 Best Waylon Jennings Albums, Ranked

4. "Rainy Day Woman"

This song from The Ramblin' Man hit number two on the country charts. Jennings sings of a rainy day woman, "I never seem to see you for the good times or the sunshine."

3. Theme from The Dukes of Hazzard (Good Ol' Boys)

This song became incredibly popular as the theme song to The Dukes of Hazzard and hit number one in 1980. Jennings also provided narration for the show and even made an in-person appearance in the last season.

2. "Luckenbach, Texas (Back to the Basics of Love)"

This popular tune from the album Ol' Waylon makes multiple country references, including Hank Williams, Mickey Newbury, and Jerry Jeff Walker. Alvin and the Chipmunks covered the song in 1981.

1. "Mamas Don't Let Your Babies Grow Up to Be Cowboys"

This duet with Willie Nelson was nominated for an Academy of Country Music Award for Single Record of the Year in 1978. One of Jennings' greatest songs of all time, this had to be number one on our list. If you've never heard this timeless song stop what you're doing and appreciate the greatness.

Other incredible songs to check out: "Good Hearted Woman," "Don't You Think This Outlaw Bit's Done Got Out Of Hand," "Dreaming my Dreams with You," "Sweet Dream Woman," "Honky Tonk Heroes" and "Are You Sure Hank Done it This Way," "Bob Wills Is Still The King," "Just To Satisfy You," "Lonesome, On'ry and Mean," and "I Ain't Living Long Like This"

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The 8 Best Waylon Jennings Songs, Ranked