If you look up the term “swagger” in the dictionary, you just might find a picture of Waylon Jennings alongside the listing. Beginning in the 1970s, Jennings started to top the charts with music that was heavy on guitar — and a pretty good dose of attitude. More than any artist, Jennings personified the “Outlaw” era with a series of classics that have stood the test of time.
However, that’s just part of the story. The era would have all pomp and circumstance were it not for two essential ingredients — great songs, and one of the most underrated vocal stylings in country music history. Go back and check out his early recordings for RCA, and you will find some work that is astonishing in scope and talent. Granted, he was still looking for his own identity when cutting records like “The Chokin’ Kind” and “MacArthur Park,” but even then, it was apparent that he was on the verge of something very special.
In this discussion of Waylon Jennings songs, we keep the focus on his solo work. After all, there are so many collaborations to consider — Jessi Colter, Johnny Cash, and Willie Nelson among then. And, as you can imagine, the majority of the selections on this list are from 1974 onward, when he began to capture lightning in a bottle. But, there are a few of his early hits that deserve a mention as well!
Best Songs: Alabama | Alan Jackson | Blake Shelton | Brad Paisley | Carrie Underwood | Chris Stapleton | Conway Twitty | Dierks Bentley | Dixie Chicks | Dolly Parton | Eric Church | Garth Brooks | George Jones | George Strait | Jason Aldean | Johnny Cash | John Denver | Keith Urban | Kenny Chesney | Kenny Rogers | Lady Antebellum | Merle Haggard | Miranda Lambert | Patsy Cline | Rascal Flatts | Reba McEntire | Shania Twain | Thomas Rhett | Tim McGraw | Toby Keith | Willie Nelson | Zac Brown Band
15. Waylon Jennings – “Brown Eyed Handsome Man”
Undoubtedly, Waylon was inspired — as many music fans were by Chuck Berry‘s iconic 1956 recording. But there might have been another artist who sparked Jennings’ interest in the song — his one-time boss Buddy Holly, who recorded the song. The song became a hit in the United Kingdom in 1963, four years after Holly’s death. Jennings’ 1970 release — which hit No. 3 on the chart — showed an artist still looking for his own musical direction, but was a significant step in the Outlaw style.
14. Waylon Jennings – “Will The Wolf Survive?”
After two decades at RCA, Jennings signed with longtime friend Jimmy Bowen and MCA Records in 1986. Critics have been mixed of his recorded output there, but he did take a few musical chances that were worth noting. His 1987 “Audiobiography,” A Man Called Hoss, was his best album for the label, but it was this debut single for the label that represented one of the most triumphant Waylon Jennings song performances of his later years, with a song originally recorded by Los Lobos. You might not find this top ten hit on many of these lists, but it’s a performance well worth searching for.
13. Waylon Jennings – “Rainy Day Woman”
By 1975, Jennings had his sound down almost to an exact science, and this No. 2 hit represented one of his most quintessential moments. The song personified the “Outlaw” movement.
12. Waylon Jennings – “Sweet Dream Woman”
This 1972 top ten is noteworthy for his vocal performance, which is one of his more restrained in his catalog. Vocally, the singer held back just a little bit on this gem of a song, and the result was one of his early moments that gave fans a hint at the style in which he was seeking to establish.
11. Waylon Jennings – “Theme From ‘The Dukes Of Hazzard'”
The biggest seller in the Jennings catalog was far from his greatest piece of writing. Any fan would tell you that. But, as the theme song to the classic CBS series from 1979-1985, Jennings hit with a song that wound up being bigger than him — known worldwide. His radio background proved beneficial for his weekly job as “The Balladeer,” the show’s narrator. He would record his intros and outros to the show at radio stations across the nation each week.
10. Waylon Jennings – “Ain’t Living Long Like This”
Perhaps the hardest rocker of Jennings’ career, this Rodney Crowell-penned song gave the singer his first hit of the 1980s. The song would later find its’ way onto the soundtrack of Grand Theft Auto V.
9. Waylon Jennings – “Amanda”
This song was a hit in the 1970s for both Don Williams and Waylon Jennings, with both artists turning in unforgettable renditions of the song. Williams recorded his version in 1973, with Jennings following suit the next year. In 1978, new instrumentation was added to the track — which made his Greatest Hits album, and the song topped the charts in June of 1979.
8. Waylon Jennings – “The Wurlitzer Prize”
As Thanksgiving 1977 neared, Jennings was in a celebratory mood with the release of this Chips Moman / Bobby Emmons composition, which was very much an old school-sounding moment. The song made an impact on a whole generation, with cover performances turned in over the years by artists such as Norah Jones and Kacey Musgraves.
7. Waylon Jennings – “Mental Revenge”
Mel Tillis wrote the song, and enjoyed a hit with it in 1976. But, the first artist to record the tune was Waylon Jennings, who showed his promise as a vocalist with this raw and bitter-edged performance that earned him a No. 12 ranking in 1967. Jennings’ version definitely influenced Hank Williams Jr., who covered the song on his 2016 Nash Icon disc It’s About Time.
6. Waylon Jennings – “Only Daddy That’ll Walk The Line”
Jimmy Bryant wrote the song, and this became third top five Waylon Jennings song in a row. It wasn’t a number one, but spent an amazing five weeks at number two. In a review of the album it was pulled from. Billboard said in 1968, complimented the singer’s “robust, compelling vocal style.” Nearly five decades later, that description is still apt.
5. Waylon Jennings – “Dreaming My Dreams With You”
The lyrics about a man looking back on a previous relationship — via the pen of Allen Reynolds — were nothing short of genius. Jennings turned in a wistful performance of the song, wringing the emotion out of every line. With covers by such artists as Rodney Crowell, Martina McBride, and Crystal Gayle, this could be the most recorded song of all of Jennings’ hits
4. Waylon Jennings – “This Time”
Record companies aren’t particularly known for their patience these days. In 1974, things were drastically different. Nine years had passed since the singer signed with RCA, and he had never hit the top of the charts. This song changed all that, becoming the first Waylon Jennings song to hit the pinnacle of the hit parade. The strong beat of the song — combined with the lyrical content about giving his significant other an ultimatum — connected with audiences in a way no Jennings release had ever done before.
3. Waylon Jennings – “Are You Sure Hank Done It This Way”
Admittedly, Jennings loved recording material every now and then to check Nashville’s sense of humor, and this 1975 release — about the changes that had taken place in the industry over the years since Hank and Lefty — took a sly poke at Music City. In 1999, Clint Black covered it for his D’Electrified album with Jennings on the track, updating it to “Are You Sure Waylon It Done It This Way?”
2. Waylon Jennings – “I’ve Always Been Crazy”
Waylon Jennings knew that he was a little different, and marched to the beat of his own drummer. In the fall of 1978, the singer topped the charts with a song that paid tribute to that difference, and talked about who he was as a person — flaws and all. It was an honest reflection of a man who was being forthright about everything, but stopping short of apologizing. After all, he was what he was — and damn proud of it!
1. Waylon Jennings – I’m A Ramblin’ Man
If you look up the term “Outlaw Music” in the dictionary, you might just find a mention of this hit for Jennings. Originally recorded by writer Ray Pennington in 1967, the song made it to No. 29 in it’s original version. With the strong tempo of the song, infectious guitar work, and hard-hitting lyrics warning a lover to stay away from this rolling stone unless she wants to get hurt, this was proof that by 1975, Waylon Jennings had effectively found his voice, perfecting his sound in the process.