October 4

Waylon Jennings and His Greatest Songs of All Time


Waylon Jennings

Waylon Jennings has been one of the pioneers of outlaw country music. He was against all the standards and rules given to him. He wanted to take control of his music and style. Eventually, his fashion and music have become a familiar image in country outlaw music.

Young Waylon

He was born on June 15, 1937, at Littlefield, Texas. Jennings’ first name was not Waylon. His mother named him Wayland. Upon knowing that Wayland was a name of a University, his mother changed his name to Waylon. Jennings learned to play the guitar at age eight. He performed in local shows in his town.

Buddy Holly

Before Jennings signed his first record label, he used to work in different radio stations. He worked at KVOW, KDAV, KVOW, KLVT, and KLLL. While working on a radio station, he met Buddy Holly, a singer-songwriter, who invited Jennings to work with him. Jennings’ first recording was with Holly. They recorded the songs “Jole Blon” and “When Sin Stops (Love Begins).” After the death of Holly, Jennings formed a new band called Waylors.

First Record Label

He first signed with Trend records and released his first solo song, “Another Blue Day.” After that, he signed again with another label, A&M Records. In 1964, he released a few records while on A&M. In 1965, Jennings earned his first song on the Billboard chart with “That’s the Chance I’ll Have to Take.” After signing a deal with the RCA Record label, Jennings began to make music that entered the Billboard chart. However, the problem was he cannot play the kind of music he wanted to play. On a book called With Amusement For All: A History of American Popular Culture Since 1830 by LeRoy Ashby, Jennings said,

“They wouldn’t let you do anything. You had to dress a certain way: you had to do everything a certain way…They keep trying to destroy me.”

After being hospitalized, he found a new manager, Neil Reshen, who renegotiated his contract with RCA. Thus, Jennings was able to do anything for his music and style.

Jennings had released a total of 96 singles and charted numerous songs. He collaborated with different artists such as Willie Nelson, a fellow country outlaw musician, his wife Jessi Colter, and many more. But did you know what Jennings’ best songs are in his entire career? Here we listed his best songs, but not in specific order.

Waylon Jennings’ Greatest Songs

“Only Daddy That’ll Walk the Line”

Jennings’ first song to hit the top of the chart was his recording of “Only Daddy That’ll Walk the Line.” The song is about a man who is tired of his woman because she only does what she wants. He reminds her of who he is in her life. Furthermore, he planned on leaving her as he cannot bear being with her.

“When I start a walkin’, gonna hear you start a squawkin’

And beggin’ me to come back home.”

Most people associate this song to Jennings. However, it was not recorded first by Jennings but by Jim Alley. This song was only made famous by Jennings. “Only Daddy That’ll Walk the Line” was written by Jimmy Bryant. It is one of the singles from his ninth album Only the Greatest. Jennings’ recording of the song placed at No. 2 on the Billboard Hot Country Songs chart. Moreover, the song reached No. 1 on the Canadian charts.

Aside from Jennings, there are other artists who covered the song. Linda Ronstadt recorded the song in 1969 for her album Hand Sown…Home Grown. Hank Williams Jr. added his version of this song to his album Family Tradition in 1979. The Kentucky Headhunters version of this song secured a spot on the Billboard Hot Country Songs chart. In addition, the band’s version was released in 1991 as part of their album Electric Barnyard.

“Good Hearted Woman”

The song “Good Hearted Woman” is also considered to be one of Waylon Jennings’ best songs. Jennings wrote the song with Willie Nelson when they were in Fort Worth, Texas. Jennings’ attention was caught when he saw an advertisement about Tina Turner and her husband, Ike Turner. The commercial said,

“A good hearted woman loving two-timing men.”

The words “Good Hearted Woman” sparked Jennings interest. Nelson was busy playing poker when Waylon told Nelson his idea. They immediately worked together until they came up with the song we now know to be one of Jennings’ best songs.

This became the lead single on Jennings’ sixteenth studio album Good Hearted Woman. Waylon released the single and the album in 1972. His solo recording of the song made it to No. 3 on the Billboard Hot Country Songs chart. In 1975, Nelson’s vocals were added to Jennings recording for their album Wanted: The Outlaws! The version of the pair reached No. 1 on the Billboard Hot Country Songs chart. In addition, it entered the Billboard Hot 100 at No. 25 and the Adult Contemporary chart at No. 16.

The following artists recorded Waylon’s song:

Moreover, George and Waylon performed this song once on stage.

“I’m a Ramblin’ Man”

Waylon Jennings was a fan of Ray Pennington when he heard the song “I’m a Ramblin’ Man.” In 1974, he was fortunate to release his version of the song. He told Pennington that he would record “Oklahoma Sunshine” and “I’m a Ramblin’ Man,” and let Pennington produce it.

Pennington’s version of the song reached No. 29 on the Billboard Hot Country Songs chart. It was Jennings who made the song place at No. 1. Therefore, this now became Jennings’ second No. 1 song on the country chart. Moreover, his song crossed over to the pop chart at No. 75. It also secured a spot on the Canadian and Australian chart.

“I’m a Ramblin’ Man” is a story of a man who goes out with different girls every time he is in another town. He never settles down, and he warns every woman that they should be careful not to fall in love with him because he will only end up breaking their hearts.

“Are You Sure Hank Done It This Way?”

Jennings was a huge fan of Hank Williams Sr. too. He wrote a song as a tribute to his favorite singer. It’s about the change in country music. He mentioned in his song that country music is far more different now because it became all about the cars and the shiny suits.

“Rhinestone suits and new shiny cars

It’s been the same way for years

We need a change.”

Waylon earned his third No. 1 song in the Billboard chart with this song. In addition, it crossed over to the US pop chart at No. 60. His song became a part of his studio album Dreaming My Dreams, released in 1975. The B-side of his record was “Bob Wills is Still the King,” a tribute to Bob Wills’ music. His album Dreaming My Dream was his first album to reach No. 1 on the Billboard Top Country Albums chart. Moreover, it was Gold-certified by RIAA.

Alabama covered the song in 2010 as a tribute to Waylon. Their version reached No. 53 on the Country Songs chart. Other country artists who recorded Waylon’s song were Clint Black and Hank Williams Jr.

“Luckenbach, Texas (Back to the Basics of Love)”

Remember George Jones’ hit song “He Stopped Loving Her Today?” Jones hated the song but it restored his career and it became one of country music’s greatest songs. A similar thing happened to Waylon, “Luckenbach Texas (Back to the Basics of Love)” became another hit song of Waylon. As he mentioned in his book, Waylon,

“I knew it was a hit song, even though I didn’t like it, and still don’t.”

This became his fourth No. 1 song on the Billboard Country Songs chart. In addition, his song entered different charts inside and outside the US. The song reached No. 25 on the Billboard pop chart, being his second biggest hit on the pop chart. Moreover, it placed at No. 16 on the Adult contemporary chart. The song was the first single from his album Ol’ Waylon, which is another No.1 album for Jennings. He was joined by Willie Nelson on the last part of the song.

The song was offered to Waylon by the songwriters Chips Moman and Bobby Emmons because his name was mentioned in the song. Even though he did not like it, he still recorded it, and it turned out to be one of his best songs.

“Luckenbach, Texas (Back to the Basics of Love)” is a story of a couple who is tired of the glamorous life. They want to run away to the small town of Luckenbach, Texas and begin a simple life.

“I’ve Always Been Crazy”

Before Waylon released his new album, he was busted by DEA in 1977 because of a package of drugs he received. They charged him, but he was not arrested for any crime due to lack of evidence. Even though he was almost caught, the sales of his album still rose and were not affected by the situation. He released his album I’ve Always Been Crazy the following year. The album reached No. 1 on the Billboard Top Country Albums chart. In addition, the album secured a spot on the Billboard 200 at No. 48. His album was all about his life and how he felt towards the changes in the music industry.

His single “I’ve Always Been Crazy” became his sixth No. 1 song on the Billboard Hot Country Songs chart. The song was written by Waylon Jennings where he expressed about the things he is going through in his life.

“I’ve always been crazy and the trouble that it’s put me through

Been busted for things that I did, and I didn’t do

I can’t say I’m proud of all of the things that I’ve done

But I can say I’ve never intentionally hurt anyone”

This became one of the best country songs because he was unapologetically honest about the things he felt and have been through.

“Mamas Don’t Let Your Babies Grow Up to Be Cowboys”

In 1978, Waylon and Nelson collaborated again for their album Waylon & Willie. In their album, they have included Ed Bruce’s song “Mamas Don’t Let Your Babies Grow Up to Be Cowboys.” Ed Bruce’s version of the song reached No. 15 on the Country chart. However, it was Waylon and Willie who made the song reach No. 1 on the Billboard chart. It may not be a solo recording of Waylon, but it was one of the best recordings by him and Willie Nelson. Furthermore, it placed at No. 42 on the Billboard Hot 100 chart. Waylon and Willie won a Grammy Award for Best Country Performance by a Duo or Group.


Don Williams was the first one to record the song, but he only charted “Amanda” at No.33 on the Billboard chart. Waylon’s version reached No. 1 on the Billboard Hot Country Songs chart. Moreover, “Amanda” secured a spot on the Billboard Hot 100 chart and the Adult Contemporary chart. The song was released twice. First, it was part of his album The Ramblin’ Man in 1974. The other version was released as a single and included on his album Greatest Hits.

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

Waylon was the narrator of the film Moonrunners in 1975. He was then invited to be the narrator of the 1970 TV series The Dukes of Hazzard which was inspired by Moonrunners. He wrote and recorded the theme song of the show. There were two versions of the song. One is for the TV show, and the other is available for his album Music Man. Waylon earned his twelfth No. 1 song on the Billboard Country chart because of this song. In addition, it was able to reach the No. 21 position of the Billboard Hot 100 chart.


This song was not a solo recording of Waylon, but it was one of the songs he recorded with other big names in country music. Jimmy Webb wrote the song “Highwayman” that tells a story of a man being reincarnated into four different people. Webb recorded the song in 1977 and made it part of his album El Mirage. In 1979, Glen Campbell released his version for his album Highwayman. Waylon Jennings, Willie Nelson, Kris Kristofferson, and Johnny Cash teamed up to form the group known as the Highwaymen. They have made the song reach No. 1 on the Billboard Hot Country chart.

There are four verses in the song about four different people but one soul. Nelson sang the part of the Highwayman, Jennings played the part of the Dam Builder, Kristofferson played the part of the Sailor, and Johnny Cash was the starship captain. This is the most famous song they have recorded altogether.

“Rose in Paradise”

Last but certainly not the least, is Waylon Jennings song “Rose in Paradise.” The song was written by Jim McBride and Stewart Harris. McBride shared to The Boot how they came up with the song. He was telling Harris about the house in Huntsville, Alabama, where a woman named Rose lived there in 1800. Five of her husbands died mysteriously. Then, after McBride shared the story, Harris began telling him another ghost story. They planned on writing a ghost story but eventually, it turned into a song about a woman who runs away from her jealous yet rich lover.

The song was recorded by Waylon because upon hearing the song Loretta Lynn said,

“Oh lord, that would be good for Waylon.”

Waylon recorded the song and made it part of his album Hangin’ Tough in 1987. The song was covered by Willie Nelson and Chris Young in 2009.

There you are folks, a compilation of Waylon Jennings’ greatest hit songs.

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Waylon Jennings

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