Waylon Jennings, with his distinctive scraggly beard, untamed hair, and deeply resonant baritone, embodied the spirit of outlaw country even before it was formally recognized as a genre. More than his Highwaymen contemporaries Johnny Cash and Willie Nelson, Jennings, a Texan through and through, radiated a rebellious charisma. This swagger defined the edgier, darker style of country music he pioneered in the 1970s, solidifying his place as a true icon.
Here are 20 essential Waylon Jennings Songs, showcasing the breadth and depth of his potent musical legacy:
- Ned Kelly
Few remember the 1970 film Ned Kelly, primarily known for featuring Mick Jagger’s acting, also boasted an intriguing soundtrack. Among the contributors was a pre-fame Waylon Jennings, lending his voice to songs penned by Shel Silverstein. The title track, an acoustic, folk-infused narrative song, sees Jennings recounting the tale of the infamous Australian outlaw. This track is a worthwhile discovery, revealing the nascent stages of Jennings’ signature sound before it fully matured into the outlaw country style he’d become known for. It highlights his storytelling ability even in a folkier context.
Waylon Jennings in Ned Kelly movie
- The Chokin’ Kind
Waylon Jennings and his band, The Waylors, initially released “The Chokin’ Kind,” written by Harlan Howard, in 1967. While it reached number 8 on the US Country chart for Jennings, it found greater success when soul singer Joe Simon recorded it, earning a Grammy Award three years later. Jennings’ rendition is raw and gritty. He portrays a man tormented by a love that feels suffocating, highlighting the darker, more troubled aspects of relationships which became a recurring theme in his work.
Waylon Jennings in Ned Kelly movie
- This Time
“This Time,” one of Waylon Jennings’ early number 1 country hits, recorded in 1973, benefited from the co-production of Willie Nelson. It leans more towards West Coast folk than traditional country, even with Mickey Raphael’s signature harmonica adding a country flavor. The song deals with themes of returning to a lover, but with a characteristic Jennings warning: mistreatment will lead to a final departure. This assertive stance on relationships is a hallmark of his outlaw persona, even in a softer, folkier setting.
Waylon Jennings in Ned Kelly movie
- Good Ol’ Boys
While not necessarily considered Waylon Jennings’ best song by all metrics, “Good Ol’ Boys” is undoubtedly one of his most widely recognized, thanks to its role as the theme song for the immensely popular 1980s television show The Dukes of Hazzard. Its catchy tune and lyrics, which in some ways foreshadowed the “big hat” commercial country style of later decades, propelled it to the top of the country charts in August 1980. This crossover appeal to a broader audience cemented its place in pop culture, even if it represents a more commercial side of Jennings.
Waylon Jennings in Ned Kelly movie
- Ladies Love Outlaws
“Ladies Love Outlaws,” the title track of his 1972 album, is widely regarded as Waylon Jennings’ first fully realized “outlaw” album. It wasn’t just the title that signaled this shift; the entire album embodied a rebellious spirit. Penned by Lee Clayton, the song perfectly encapsulated Jennings’ “doing it my way” image. The inclusion of Waylon and his wife Jessi Colter’s names in the final verse further personalized the outlaw image, linking it directly to his life and relationships.
Waylon Jennings in Ned Kelly movie
- Are You Sure Hank Done It This Way
“Are You Sure Hank Done It This Way” is another Jennings original that delves into the challenges and tribulations of a musician’s life on the road. The lyrics paint a picture of a touring musician weary of the grind. Musically, it features the distinctive, stomping country beat that became closely associated with Waylon Jennings’ signature sound. Although it only held the top spot on the country charts for a week, its evocative lyrics and rhythmic drive made it a lasting fan favorite and a staple of his live performances.
Waylon Jennings in Ned Kelly movie
- Bob Wills Is Still the King
“Bob Wills Is Still the King” is a heartfelt tribute to Western Swing music and the state of Texas. Jennings proudly proclaims his Texas roots and acknowledges Bob Wills, a pioneer of Western Swing, as a musical hero. Originally released as the B-side to “Are You Sure Hank Done It This Way,” it gained significant airplay on its own merit. The song is pure Waylon, even name-dropping Willie Nelson. Around the three-quarter mark, the tempo shifts, briefly incorporating the Western Swing style of Bob Wills, creating a direct musical homage.
Waylon Jennings in Ned Kelly movie
- Waymore’s Blues
“Waymore’s Blues” is a deeper cut, not a major hit, but a beloved track among dedicated Waylon Jennings fans. Featured on his 1975 album Dreaming My Dreams, his first million-selling, gold-certified release, it showcases a more introspective side. The stripped-down arrangement has a jazzy undercurrent, driven by electric piano, and the lyrics are intensely personal and seemingly autobiographical. They candidly address his struggles with infidelity, a theme that resonates with the raw honesty characteristic of outlaw country.
Waylon Jennings in Ned Kelly movie
- Are You Ready for the Country
Neil Young initially recorded “Are You Ready for the Country” as a deep track on his Harvest album, never releasing it as a single. Waylon Jennings took the song and made it the title track of his 1976 album, transforming it into a signature tune. The lyrics, particularly the repeated question “Are you ready for the country? Are you ready for me?” became an anthem of sorts, embodying the outlaw spirit and rural pride. Jennings even re-recorded it in 1995, produced by his son Shooter, demonstrating its enduring appeal throughout his career.
Waylon Jennings in Ned Kelly movie
- Ain’t Living Long Like This
Rodney Crowell’s country rocker, “Ain’t Living Long Like This,” also famously recorded by Emmylou Harris, was a perfect fit for Waylon Jennings’ “lonesome, ornery and mean” persona. The song, from the perspective of a criminal reflecting on his life, resonated deeply with Jennings’ outlaw image. His 1979 version became a number 1 country hit, achieving chart success that previous recordings hadn’t. More recently, younger audiences and gamers might recognize it from its inclusion in the Grand Theft Auto V soundtrack, further extending its reach.
Waylon Jennings in Ned Kelly movie
- Only Daddy That’ll Walk the Line
“Only Daddy That’ll Walk the Line” narrowly missed the top spot in 1968, reaching number 2 on the country charts. This song blended soulful backing vocals and organ with a modified country twang that was characteristic of the era. Even seemingly simple lines like “Everybody knows you’ve been steppin’ on my toes” carry a menacing undertone in Jennings’ delivery. The song is a warning to a girlfriend testing his patience, threatening to leave her to deal with her “funny little moods.” It showcases his ability to infuse even mainstream country sounds with his outlaw edge.
Waylon Jennings in Ned Kelly movie
- Luckenbach, Texas (Back to the Basics of Love)
Ironically, Waylon Jennings claimed to dislike “Luckenbach, Texas (Back to the Basics of Love),” a classic written by Chips Moman and Bobby Emmons. Despite his personal feelings, it became a massive hit, reaching number 1 on the country chart and number 25 on the pop charts in 1977. Perhaps his reluctance stemmed from being name-checked in the lyrics alongside Willie Nelson (who actually guests on the final chorus), Hank Williams, and Mickey Newbury. The song’s bittersweet story of a wealthy couple seeking to rekindle their love in the small town of Luckenbach resonated with audiences, making it one of Jennings’ most commercially successful and enduring songs.
Waylon Jennings in Ned Kelly movie
- Mammas Don’t Let Your Babies Grow Up to Be Cowboys
“Mammas Don’t Let Your Babies Grow Up to Be Cowboys” is equally associated with both Willie Nelson and Waylon Jennings. This 1978 duet topped the country charts and perfectly captured the contrasting vocal styles of Nelson’s delicate quiver and Jennings’ booming growl. The song became an instant classic due to its simple yet powerful message, warning mothers against raising sons who prioritize songs and cowboy lifestyles over material wealth and stability. Its timeless theme of romanticizing the cowboy life while acknowledging its hardships struck a chord with listeners across generations.
Waylon Jennings in Ned Kelly movie
- I May Be Used (But Baby I Ain’t Used Up)
“I May Be Used (But Baby I Ain’t Used Up),” released in 1984, is a testament to Waylon Jennings’ enduring virility and defiant spirit. At 46, Jennings sings with a gruff, world-weary voice that belies his age, projecting the persona of a man older than his years. Despite the wear and tear of life, he asserts his readiness for love and passion, famously proclaiming, “It ain’t how you look, it’s what you got under the hood.” This raw, unapologetic sexuality, delivered with his characteristic swagger, made it a memorable and humorous hit.
Waylon Jennings in Ned Kelly movie
- I’m a Ramblin’ Man
Not to be confused with songs of the same name by Hank Williams Sr. or The Allman Brothers Band, Waylon Jennings’ “I’m a Ramblin’ Man,” written by Ray Pennington, perfectly captures his restless spirit. The song’s driving, “clippity-clop” rhythm and Jennings’ direct warning against emotional attachment – “cause he’s, you know, a rambling man” – became an anthem for his vagabond image. Ironically, Jessi Colter, his wife, did not heed this warning, highlighting the complex relationship between his public persona and personal life.
Waylon Jennings in Ned Kelly movie
- I’ve Always Been Crazy
“I’ve Always Been Crazy,” a self-penned number 1 country hit from 1978, was written during Waylon Jennings’ well-documented period of cocaine abuse. The song is reflective and melancholic, a twangy ballad with apologetic lyrics. Lines like “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” reveal a vulnerability rarely seen in his more outwardly rebellious songs. It’s one of his most personal and confessional recordings, offering a glimpse behind the outlaw facade.
Waylon Jennings in Ned Kelly movie
- Lonesome, On’ry & Mean
“Lonesome, On’ry & Mean,” the title track of Jennings’ first album under his RCA contract that granted him artistic control, was a pivotal song in defining his outlaw image. While not written by him (Steve Young penned it), it perfectly encapsulated his renegade spirit. The song served as a powerful re-introduction of a new, ruggedly individualistic Waylon to the music world. It tells the story of a trucker whose hard life on the road has shaped his “lonesome, on’ry & mean” personality, a label he ultimately rejects in the final verse, adding a layer of complexity to the outlaw archetype.
Waylon Jennings in Ned Kelly movie
- Rainy Day Woman
“Rainy Day Woman,” an early gem from 1974 co-written with fellow outlaw Tompall Glaser, leans slightly more traditional than some of his later, edgier work. Its infectious melody propelled it to number 2 on the country charts. Despite its upbeat tempo and catchy pedal steel solo, the song’s lyrics reveal a more exasperated and less traditionally “outlaw” sentiment. It tells the story of a man frustrated by a perpetually pessimistic woman, capturing a relatable everyday relationship dynamic with Jennings’ characteristic vocal delivery.
Waylon Jennings in Ned Kelly movie
- Closing In on the Fire
“Closing In on the Fire,” the title track from Waylon Jennings’ final studio album released in 1998, marked a powerful comeback. This sizzling swamp rock track, written by Tony Joe White, the genre’s king, showcased Jennings’ undiminished vocal power. His growling vocals, accompanied by a haunting harmonica and soulful gospel backing vocals, proved that even late in his career (he passed away four years later), Jennings still possessed remarkable creative energy and musical vitality, pushing boundaries and exploring new sounds.
Waylon Jennings in Ned Kelly movie
- Honky Tonk Heroes
“Honky Tonk Heroes,” the title track of the 1973 album that catapulted both Waylon Jennings and songwriter Billy Joe Shaver (who penned this and most of the album) to widespread fame, is arguably his most essential song. While not a chart-topping hit itself, it was transformative. The song’s raw, edgy blend of country with rock and roll energy defined Jennings’ outlaw persona and charted a new course for country music. It’s a cornerstone of the outlaw country movement and remains a definitive statement of Jennings’ artistic vision and rebellious spirit.
Waylon Jennings in Ned Kelly movie
Listen to Holler’s The Best Waylon Jennings Songs playlist below:
For more on Waylon Jennings, explore further:
Waylon Jennings Artist Page
Written by Hal Horowitz
Waylon Jennings in Ned Kelly movie
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