Waylon Jennings is a country music icon. The Littlefield native's first band was The Texas Longhorns, after all, and he caught a huge break from Lubbock legend Buddy Holly. 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 by RCA Records in 1976 featuring Willie Nelson, Tompall Glaser and Jennings' wife Jessi Colter. The compilation 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"
7. "Rose in Paradise"
This song was the twelfth No. 1 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 No. 1 on the country charts for a week in 1967. The title track from Jennings 1974 album that also gave us future No. 1 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 No. 1 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)"
1. "Mammas 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 Ed Bruce classic had to be No. 1 on our list. If you've never heard this timeless song, please stop what you're doing and appreciate its 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," "Will the Wolf Survive," "Drinkin' and Dreamin'," "Come With Me," "Never Could Toe the Mark," "The Chokin' Kind," "Working Without a Net," "Women Do Know How to Carry On," "Waymore's Blues," "Are You Ready For the Country," "The Wurlitzer Prize (I Don't Want to Get Over You)" and "I Ain't Living Long Like This"
This story previously ran in 2019.