The Best 20 Waylon Jennings Songs
Waylon Jennings was an American musician with a great voice and a strong personality. As a leading pioneer of the outlaw movement in country music, his raw sound has inspired generations of talent. Jennings was also a professional actor, with prominent roles in feature films and TV shows. His music always took the lead, however, with records released over many years from the 1960s to the 2010s. Jennings passed in 2002 due to complications from diabetes, with his hard life of drinking, drugs, and poor eating habits finally catching up with him.
This incredible artist released tons of great music during his long career, from traditional ballads to love songs and country rock classics. The following top 20 Jennings songs are among his very best.
‘Ned Kelly’
Ned Kelly was an iconic Australian bushranger who lived in the late 1800s. As a rugged outlaw musician, Jennings had a fondness for his bravery and larrikin spirit.
The “Ned Kelly” song was recorded by Jennings for the 1970 film about the Australian outlaw. It was the opening track, with Jennings also recording five other popular songs. Mick Jagger and Kris Kristofferson were two other artists on the soundtrack, so Jennings was definitely in good company. Jennings added his usual country swagger on this song, with his personality shining through.
‘The Chokin Kind’
This song was originally recorded and released in 1967 by Waylon Jennings. Written by Nashville songwriter Harlan Howard, it was a hit for Jennings during the first decade of his career.
“The Chokin’ Kind” reached No. 8 on the US Hot Country Singles chart, solidifying Jennings as a country star. This song featured on his 1968 album, Hangin’ On, which was his eighth studio album release. Waylon loved this song immediately when he heard it, saying, “I remember the first time I’d heard that…I flipped over that song. I loved that song.” The melody is pretty straight by itself, with Waylon’s raw voice responsible for giving it wings.
‘This Time’
Released in 1974, “This Time” was the lead single and title track of a much-loved album. It reached No. 1 on the Billboard Hot Country Singles chart, which was a notable first for Waylon Jennings. While he’d achieved multiple top 10 hits in the ’60s and early ’70s, the top position had always alluded him.
This Time the album also came out in 1974, at the very peak of the outlaw country movement. The long-player was produced by Jennings with Willie Nelson, and it was immediately loved by fans and critics alike. Four of the 12 songs were written by Nelson himself, including a few notable love songs.
‘Good Ol’ Boys’
This is the theme song from the iconic Dukes of Hazzard TV series. Written and recorded by Jennings in 1980, it set the tone for the exciting adventures of Luke Duke, Bo Duke, and the gang. The TV show was a massive hit, running from 1979 to 1985 all over the world.
This song by Jennings was also a big hit, reaching No. 1 on the Billboard Hot Country Singles chart. “Good Ol’ Boys” spent 17 long weeks on the chart, becoming his 12th No. 1. It also brought Jennings mainstream music success, reaching No. 21 on the Billboard Hot 100.
‘Ladies Love Outlaws’
This song is the title track from Jennings’ hit 1972 album. Released on RCA Nashville, it came out at a significant time in the musician’s career. His previous album, Good Hearted Woman, saw a new musical style, and this release cemented the change. With this song and album, he embraced the emerging outlaw country musical style and image.
The sounds were raw, the rhythms were sexy, and the image was definitely more edgy. “Ladies Love Outlaws” is the signature song from this movement, and it made major waves upon release.
‘Are You Sure Hank Done It This Way’
This song was written and recorded by Jennings in August 1975. It was the first single from his Dreaming My Dreams album, which would become one of his most popular. “Are You Sure Hank Done It This Way” was a massive hit for the country rebel and his third No. 1 on the country charts after “This Time” and “I’m a Ramblin’ Man.”
This iconic track quickly became an anthem, and even today, it’s recognized as a signature of the outlaw country movement. This song pays homage to the legendary Hank Williams, holding him up as an authentic figure while criticizing the glitz and glamour associated with modern country artists. This was one of his most popular songs.
‘Bob Wills Is Still the King’
This track also pays homage to a country great, this time to American swing icon Bob Wills. This song was released in two versions — as a live recording on the album Dreaming My Dreams and as the B-side to “Are You Sure Hank Done It This Way.”
While the A-side of this release was a huge hit in the ’70s, this number also became a cult classic. It was a radio favorite in the Deep South for many years, and it’s considered an important track in the history of country music. This track alludes to the Wills song “San Antonio Rose,” and it also references fellow outlaw musician Willie Nelson. This track is a definite inclusion on any “best of” Jennings songs list.
Waymore’s Blues
Also from his Dreaming My Dreams album, “Waymore’s Blues” is a testosterone-driven track fueled by drug use and relationship breakdowns. While recording this number, producer Clement tried to eject Jennings’ wife from the control room. The two men had a disagreement, and Jennings left the studio for two weeks before making a return.
When Jennings attempted to rerecord “Waymore’s Blues,” he couldn’t recapture the feeling of the original. That explains the rather sharp fade toward the end of the song, which was needed to cover up the sound of Jennings leaving the room.
Are You Ready for the Country
This famous song was the title number from Jennings’ 1976 album. It was originally written by Neil Young for his iconic 1972 Harvest album, with Jennings transforming it into a solid country song. Jennings altered the lyrics to fit his bad-boy style, changing “Are you ready for the country / Because it’s time to go” to “Are you ready for the country? / Are you ready for me?”
This song and album followed the hugely successful Wanted! The Outlaws compilation, which united the outlaw country talents of Waylon Jennings, Willie Nelson, Jessi Colter, and Tompall Glaser. “Are You Ready for the Country” is one of the best Waylon Jennings songs of them all.
I Ain’t Living Long Like This
This song has an interesting history in the country music scene. Originally written by Rodney Crowell, it was recorded by Gary Stewart in 1977 and Emmylou Harris in 1978. “I Ain’t Living Long Like This” was also recorded by Waylon Jennings in 1979, when it was released on his popular album What Goes Around Comes Around. This version was a massive hit for the outlaw musician, quickly becoming his 11th country No. 1.
While the early-’70s records released by Jennings get the most critical acclaim for good reason, it’s top songs like this that kept Jennings relevant into the 1980s and beyond.
Only Daddy That’ll Walk the Line
This song was written by Jimmy Bryant and recorded by Jennings in 1968. A big hit early in his career, it was pivotal to his later success. Jennings recorded this song at RCA Victor Studios in Nashville, with the famous Chet Atkins sitting behind the mixing desk as the producer. It was the second single from his Only the Greatest album, with the song’s robust vocals helping to cement Jennings as a star.
According to critics, “Walk On Out of My Mind” and “Only Daddy That’ll Walk the Line” are the most compelling tunes from this iconic long-player. Waylon Jennings songs don’t get much better than this.
Luckenbach, Texas (Back to the Basics of Love)
This song came out in April 1977 as the first single from the Ol’ Waylon studio album. It was written by Chips Moman and Bobby Emmons, who offered it to Jennings thinking he was the perfect fit. Jennings wasn’t a fan himself, saying this many years later in his autobiography: “I knew it was a hit song, even though I didn’t like it, and still don’t.”
“Luckenbach, Texas (Back to the Basics of Love)” is about a high-society couple who make a profound realization. Despite being rich, they’re always fighting and struggling with “the basics of love.” The final refrain of the music features fellow outlaw country star Willie Nelson.
Mammas Don’t Let Your Babies Grow Up to Be Cowboys
Another song with a varied history, “Mammas Don’t Let Your Babies Grow Up to Be Cowboys” has been released by multiple country artists. It was written and first recorded by Ed Bruce with his wife, Patsy, before being recorded by Chris LeDoux later in 1976. Waylon Jennings and Willie Nelson have the best version, however, with the famous duo covering the song on their 1978 duet album, Waylon & Willie.
This song reached No. 1 on the country chart, and it’s also featured in many films and TV commercials over the years.
I May Be Used (but Baby I Ain’t Used Up)
This song came fairly late in Waylon Jennings’ career, hitting the shelves and airwaves in 1984. “I May Be Used (but Baby I Ain’t Used Up)” was written by Bob McDill and recorded by Jennings for his Waylon and Company studio album. While the country outlaw had passed his career peak, this track still reached No. 4 on the Hot Country Songs chart.
“I May Be Used (but Baby I Ain’t Used Up)” sees a 46-year-old Jennings get down and dirty, singing, “It ain’t how you look, it’s what you got under the hood.”
I’m a Ramblin’ Man
The title of this song has been used on many tracks, including well-known hits by Hank Williams and The Allman Brothers Band. This number was written by Ray Pennington, however, and recorded by Jennings in 1967 with a distinct clippety-clop beat.
While it only stayed on the country chart for a week, “I’m a Ramblin’ Man” is notable for being Jennings’ second No. 1 on it. The song has enjoyed something of a comeback, having featured on the official soundtrack of the 2024 Marvel film Deadpool & Wolverine.
I’ve Always Been Crazy
This self-penned country music classic was recorded and released in 1978. It was another country No. 1 by Jennings, with its reflective lyrics and iconic twang coming out during a difficult time for the singer.
After years of recording and touring in the late ’60s and early ’70s, he was in the midst of cocaine abuse while recording this single. The words of this song are almost apologetic, with Jennings singing, “I can’t say I’m proud of all the things that I’ve done / But I can say I’ve never intentionally hurt anyone.”
Lonesome, On’ry Mean
This great track is the title of Jennings’ first RCA label album with total control. Released in 1973, it’s considered an important milestone in the history of country music.
Like the rest of the album, this song has a rugged style that would define the singer’s 1970s output. “Lonesome, On’ry Mean” follows a trucker on the road. It’s about searching for meaning in a chaotic world and moving forward despite the challenges. More than a romantic ideal, however, “Lonesome, On’ry Mean” is about the cost of living life on your own terms.
Rainy Day Woman
This song is a gem from peak ’70s Jennings, although this one hits a more traditional country vein. It was released in 1974, and the singer partners with Tompall Glaser on songwriting credits. “Rainy Day Woman” features a catchy melody and distinct vocal delivery, which pushed the song to No. 2 on the country music chart. It has a captivating groove and fantastic pedal steel solo, combined with an angry story about a woman who never sees the bright side of life.
As Jennings sings, “If it ain’t one thing / It’s another one on the way,” you can’t help but feel his frustration.
Closing In on the Fire
This song was released very late in the singer’s career, coming out on Ark 21 Records in 1998. On this number, the singer incorporated elements of blues and rock with his traditional country sound. It was released on an album of the same name, which also featured contributions from Sting and Tony Joe White, among other artists. As you might expect given these celebrity names, the album was much more eclectic than Jennings’ previous releases.
When it comes to great songs, this one is right up there.
Honky Tonk Heroes
“Honky Tonk Heroes” is a country single and album released by Waylon Jennings in 1973. It features all the elements of the outlaw sound, which added a raw rock-and-roll vibe to a revived honky-tonk sound.
This famous song was co-written by Billy Joe Shaver. Jennings invited the then-unknown songwriter to Nashville after hearing him sing “Willy the Wandering Gypsy and Me” from the back of a camper. This album was widely respected for its robust and no-nonsense sound.
Final Thoughts
Waylon Jennings is an iconic country figure and outlaw music figurehead. He released tons of great music over his long career, with the songs on this list among the very best. If you like your country music raw and uncompromising, Jennings’ greatest hit songs should definitely be on your next playlist.
Head over to USA Heroes Radio to hear Waylon and more iconic country artists from the past and present.
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