The 28 Best Waylon Jennings Songs, from Luckenbach to Amanda

What is Waylon Jennings' most famous song?

"Luckenbach, Texas (Back to the Basics of Love)" is Waylon Jennings' most famous song, a 1977 number one that made a tiny Texas town a pilgrimage site. "Mammas Don't Let Your Babies Grow Up to Be Cowboys", his duet with Willie Nelson, won a Grammy, and "Good Ol' Boys", the theme from The Dukes of Hazzard, introduced him to a whole generation of TV viewers.

Early Waylon Jennings songs

1. "Only Daddy That'll Walk the Line", 1968: a driving early hit that showed his rock and roll edge.
2. "Ladies Love Outlaws", 1972: an early song that helped popularize the outlaw label.
3. "Good Hearted Woman", 1972: written with Willie Nelson, later a duet number one.
4. "Lonesome, On'ry and Mean", 1973: a defiant anthem of the outlaw style.
5. "Honky Tonk Heroes", 1973: the title track of an album of Billy Joe Shaver songs.

Waylon Jennings' outlaw-era hits

6. "This Time", 1974: his first number one on the country chart.
7. "I'm a Ramblin' Man", 1974: a restless, swaggering number one.
8. "Rainy Day Woman", 1974: a laid-back love song.
9. "Dreaming My Dreams with You", 1975: one of his most tender ballads.
10. "Are You Sure Hank Done It This Way", 1975: a pointed question to Nashville about tradition.
11. "Bob Wills Is Still the King", 1975: a tribute to the Western swing legend.
12. "Waymore's Blues", 1975: a gritty blues built on his nickname.
13. "Luckenbach, Texas (Back to the Basics of Love)", 1977: his signature song.
14. "I've Always Been Crazy", 1978: an honest look at his wild reputation.
15. "Don't You Think This Outlaw Bit's Done Got Out of Hand", 1978: a wry song about the outlaw image.
16. "Amanda", 1979: a gentle love song that became one of his biggest hits.
17. "I Ain't Living Long Like This", 1979: a Rodney Crowell song turned into a number one.

Waylon and Willie: the duets

18. "Good Hearted Woman", 1976: the live duet version that topped the chart.
19. "Mammas Don't Let Your Babies Grow Up to Be Cowboys", 1978: a Grammy-winning number one.
20. "Just to Satisfy You", 1982: another number one from the pair.

Waylon Jennings songs of the 80s

21. "Theme from The Dukes of Hazzard (Good Ol' Boys)", 1980: the TV theme he also narrated.
22. "Clyde", 1980: a cover of a J.J. Cale song.
23. "Storms Never Last", 1981: a duet with his wife, Jessi Colter.
24. "Lucille (You Won't Do Your Daddy's Will)", 1983: a rocking number one.
25. "Never Could Toe the Mark", 1984: a song about never fitting the mold.
26. "Highwayman", 1985: the title song of The Highwaymen with Johnny Cash, Willie Nelson and Kris Kristofferson.
27. "Rose in Paradise", 1987: a dark story song and his last number one.
28. "Desperados Waiting for a Train", 1985: The Highwaymen's take on the Guy Clark classic.

Who was Waylon Jennings?

Waylon Jennings was born in 1937 in Littlefield, Texas, and started as a radio DJ before Buddy Holly hired him to play bass in 1958. In the 1970s he fought for the right to choose his own songs and musicians instead of using Nashville's session players, a stand that helped create the outlaw country movement with Willie Nelson, Jessi Colter and Tompall Glaser. He was inducted into the Country Music Hall of Fame in 2001 and died the following year.

The day the music died

In February 1959, Waylon Jennings was touring with Buddy Holly. He gave up his seat on a small plane to J.P. Richardson, known as The Big Bopper, who had the flu. The plane crashed after takeoff from Iowa, killing Holly, Richardson, Ritchie Valens and the pilot. Jennings said for years that a joking exchange with Holly before the flight haunted him, and the tragedy shaped the rest of his life.

Wanted! The Outlaws

In 1976, RCA released Wanted! The Outlaws, a compilation of songs by Waylon Jennings, Willie Nelson, Jessi Colter and Tompall Glaser. It became the first country album certified platinum, proving that the outlaw sound could sell to rock and country fans alike, and it featured the live duet of "Good Hearted Woman" that went to number one.

The story behind Luckenbach, Texas

Songwriters Chips Moman and Bobby Emmons wrote "Luckenbach, Texas" about trading the fast life for simple love, using the tiny Hill Country town as a symbol. Jennings had never been there when he recorded it. The song went to number one in 1977, and the town, with a population of just a handful of people, became a destination for fans that still hosts concerts today.

The Highwaymen

In 1985, Waylon Jennings, Johnny Cash, Willie Nelson and Kris Kristofferson formed The Highwaymen, a country supergroup. Their first single, "Highwayman", went to number one, and they released three albums together and toured the world. For more Texas country classics, from Willie Nelson to Waylon himself, see our songs about Texas.

The Waylon sound

Waylon Jennings is instantly recognizable: a deep, rumbling baritone over a thumping bass line and the twangy, phased tone of his Fender Telecaster, famously wrapped in black and white leather. Where Nashville records of the time used strings and background choirs, his records sounded lean and loud, closer to rock and roll and the blues. That sound influenced generations of country artists, from Hank Williams Jr. to Sturgill Simpson and Chris Stapleton.

Waylon Jennings' essential albums

• Lonesome, On'ry and Mean (1973) and Honky Tonk Heroes (1973): the albums where he took control of his sound.
• Dreaming My Dreams (1975): often named his finest album.
• Wanted! The Outlaws (1976): the landmark compilation with Willie Nelson, Jessi Colter and Tompall Glaser.
• Ol' Waylon (1977): home of "Luckenbach, Texas".
• Waylon and Willie (1978): featuring "Mammas Don't Let Your Babies Grow Up to Be Cowboys".
• Highwayman (1985): the first album by the country supergroup.

Waylon's family legacy

Waylon married singer Jessi Colter in 1969, and they recorded together throughout their lives, including the hit duet "Storms Never Last". Their son, Shooter Jennings, became a musician and producer in his own right, keeping the family name at the heart of outlaw and Americana music.

Waylon Jennings songs for a memorial

For a celebration of life, "Dreaming My Dreams with You", "Amanda" and "Storms Never Last" are gentle and personal, and "Luckenbach, Texas" is a fitting farewell for a true country fan. See our country funeral songs for more ideas.

Waylon Jennings songs for a road trip

For the open road, start with "I'm a Ramblin' Man", add "Good Ol' Boys" and "Mammas Don't Let Your Babies Grow Up to Be Cowboys" and finish with "Highwayman" as the sun goes down. See our road trip songs for more.

More classic country artists

For more great country catalogs, see our Brooks and Dunn songs, Conway Twitty songs, Dwight Yoakam songs, Kris Kristofferson songs and our 90s country songs.

A country song with an outlaw spirit

For a fan of Waylon, a personalized country song can tell their own story with a deep voice and a thumping rhythm: their name, their hometown and the road they have traveled. It makes a great birthday, retirement or Father's Day gift.

How to create a personalized country song

1. Choose a style from 14 genres: country, rock, folk and more.
2. Add their name.
3. Share three memories or details about them.
4. Review the lyrics and edit or regenerate them for free before any music is made.
5. Listen to 4 free 45-second previews and choose your favorite.

The full 3 to 4 minute song costs $35.99, or $40.99 for Premium with four full versions and editable lyrics. You get the MP3, a gift page and the lyrics as a PDF.

Give them a country song of their own: create a song and hear four previews for free.