Waylon Jennings wasn’t just a country music icon—he was a trailblazer who redefined the genre with his rebellious spirit and unmistakable voice. Known for his role in the Outlaw Country movement of the 1970s, Jennings broke away from the polished Nashville sound and carved out a road all his own, blending traditional country with rock, blues, and honky-tonk grit. His music spoke to the raw, unvarnished truth of life, love, and loss, resonating with fans who craved authenticity. From gritty tales of heartache to defiant anthems of independence, Jennings’ discography is packed with timeless classics that have left an indelible mark on the world of country music. In this list, we’re counting down the top 10 most popular Waylon Jennings songs of all time—tracks that not only dominated the charts but also helped shape the very essence of country music. Whether you’re a lifelong fan or just discovering the legend that is Waylon, these songs are sure to remind you why Jennings remains one of the most influential and beloved artists in music history. So, grab your cowboy hat, and let’s dive into the very best of Waylon Jennings!
1. “Mammas Don’t Let Your Babies Grow Up to Be Cowboys” (1978)
Released in 1978 as part of the iconic Waylon & Willie album, “Mammas Don’t Let Your Babies Grow Up to Be Cowboys” is a duet that showcases the undeniable chemistry between Waylon Jennings and Willie Nelson. Written by the talented duo of Ed and Patsy Bruce, this song serves as a charming yet bittersweet cautionary tale from mothers to their sons. The lyrics warn of the rough, uncertain life that comes with being a cowboy—a life filled with adventure but also fraught with challenges. Jennings’ deep, resonant voice blends beautifully with Nelson’s distinctive twang, creating a timeless anthem that perfectly encapsulates the Outlaw Country genre. The track’s mix of humor, warmth, and a dose of realism struck a chord with millions of listeners, making it not just a country classic, but a crossover hit that appealed to fans of various genres. Its themes of independence and rugged individualism resonate strongly, while the catchy chorus ensures it remains a favorite among Jennings’ fans. This song’s enduring popularity is a testament to its relatable message and the stellar collaboration between two of country music’s legends.
2. “Good Hearted Woman” (1972)
“Good Hearted Woman,” first released by Waylon Jennings in 1972, found its way into the hearts of listeners when Jennings teamed up with Willie Nelson for a live duet in 1976. This beloved track, co-written by Jennings and Nelson, pays tribute to the steadfast women who loyally support their outlaw men, despite the turmoil that often comes with that lifestyle. Jennings’ smooth delivery, combined with the song’s heartfelt lyrics, made it a staple of country music. The upbeat tempo and relatable narrative helped solidify Jennings’ status as a leading figure in the genre. The live rendition is particularly special, as it captures the camaraderie and chemistry between Jennings and Nelson, adding an extra layer of authenticity and charm to the performance. It’s not just a song; it’s a celebration of love, loyalty, and the complexities of relationships, making it resonate deeply with fans and newcomers alike.
3. “Luckenbach, Texas (Back to the Basics of Love)” (1977)
“Luckenbach, Texas (Back to the Basics of Love),” released in 1977 as part of the Ol’ Waylon album, stands out as one of Waylon Jennings’ most iconic tracks. In this heartfelt anthem, Jennings invites listeners to escape the hustle and bustle of modern life and return to simpler times, where love and authenticity reign supreme. The song paints a vivid picture of the small Texas town of Luckenbach, embodying the laid-back spirit of the Outlaw Country movement. With its easygoing melody and Jennings’ relaxed vocals, the track evokes a sense of nostalgia that resonates with many. It quickly became a massive hit, soaring to #1 on the country charts and remaining a fan favorite for its evocative portrayal of rural life. The song’s philosophical musings on love and happiness, combined with its catchy refrain, have solidified its status as a timeless classic that continues to be cherished by country music lovers today.
4. “Are You Sure Hank Done It This Way” (1975)
In 1975, Waylon Jennings boldly expressed his frustrations with the commercialization of country music through “Are You Sure Hank Done It This Way.” Featured on the Dreaming My Dreams album, this track serves as both a critique of the Nashville music machine and a tribute to the legendary Hank Williams, one of country music’s greatest icons. With its driving beat and defiant lyrics, Jennings questions whether the pioneers of the genre would have approved of the slick, polished direction country music was heading. The song resonated deeply with fans and fellow artists alike, quickly becoming an anthem for the Outlaw Country movement. Jennings’ fierce determination to return country music to its raw and authentic roots helped solidify his status as a leader of this transformative movement, earning him respect and admiration from listeners who craved a more genuine sound in their music.
5. “I’ve Always Been Crazy” (1978)
“I’ve Always Been Crazy,” released in 1978 on the album of the same name, stands out as one of Waylon Jennings’ most autobiographical songs. In this track, Jennings candidly reflects on his life as a rebel, embracing both the joys and the pitfalls that accompany his unconventional lifestyle. With the memorable line, “I’ve always been crazy, but it’s kept me from going insane,” Jennings captures the essence of the Outlaw Country artist, proudly acknowledging his status as an outsider. The playful yet introspective nature of the song made it a hit, climbing the country charts and resonating with listeners who admired Jennings for his unfiltered honesty and fearless approach to life and music. This track serves as an anthem for those who embrace their individuality, celebrating the beautiful chaos that often accompanies a life lived authentically.
6. “Lonesome, On’ry and Mean” (1973)
A pivotal release in Waylon Jennings’ career, “Lonesome, On’ry and Mean” emerged in 1973 as the title track of his album. This song marked Jennings’ full embrace of the Outlaw Country movement, featuring gritty lyrics and a raw, rebellious energy that resonated deeply with fans. Written by Steve Young, the track tells the story of a man hardened by life on the road, who refuses to conform to societal expectations. Jennings’ gravelly voice and the relentless rhythm of the song capture the essence of the outlaw spirit, making it a defining moment in his transformation from a Nashville outsider to a country music pioneer. The song became a rallying cry for those who rejected the mainstream, polished sound of country in favor of something more authentic and raw, solidifying Jennings’ legacy as a torchbearer for the Outlaw Country movement.
7. “Amanda” (1974)
Originally released in 1974 on The Ramblin’ Man album, “Amanda” stands out as one of Waylon Jennings’ most tender and heartfelt ballads. Written by Bob McDill, the song serves as a beautiful ode to a woman named Amanda, whose love is celebrated with quiet reverence. Jennings’ deep, gravelly voice adds a layer of sincerity and emotional depth to the song, making it a favorite among fans. While it didn’t achieve immediate commercial success, the song gained renewed popularity when it was included on Jennings’ 1979 Greatest Hits album, where its poignant lyrics and simple beauty shone through. “Amanda” is notable for its stripped-back production, allowing Jennings’ voice and the song’s touching message to take center stage, making it an enduring classic that resonates with listeners of all ages.
8. “This Time” (1974)
“This Time,” released in 1974 from the album of the same name, marked a significant turning point in Waylon Jennings’ career. This track was not only the first song Jennings wrote and produced entirely on his own but also symbolized his newfound creative freedom after years of battling with record labels. The song’s smooth, laid-back groove and Jennings’ understated delivery made it an instant hit, reaching #1 on the country charts. Lyrically, “This Time” speaks to themes of redemption and personal growth, with Jennings vowing to make amends for past mistakes. Its success helped cement Jennings’ place as a key figure in the Outlaw Country movement, showcasing his ability to thrive on his own terms while delivering music that resonates deeply with his audience.
9. “Only Daddy That’ll Walk the Line” (1968)
Waylon Jennings’ 1968 hit “Only Daddy That’ll Walk the Line” catapulted him into the national spotlight and showcased his early experimentation with a more rock-influenced sound, blending his country roots with an infectious rhythm. Released on the Only the Greatest album, this song tells the story of a man standing his ground against a domineering woman, and Jennings’ commanding vocal performance adds a swagger that makes the track irresistible. The song became a significant success, reaching #2 on the country charts and marking one of Jennings’ first big hits. Its edgy tone foreshadowed the rebellious direction that Jennings would later embrace, setting the stage for his emergence as a defining figure in country music.
10. “The Wurlitzer Prize (I Don’t Want to Get Over You)” (1977)
Released in 1977 on the Waylon & Willie album, “The Wurlitzer Prize (I Don’t Want to Get Over You)” is a beautifully melancholic song that showcases the softer side of Waylon Jennings. Written by Chips Moman and Bobby Emmons, this track features Jennings lamenting a lost love while finding solace in the music emanating from a Wurlitzer jukebox. The slow, mournful melody, paired with Jennings’ tender vocals, creates an atmosphere of quiet despair that resonates deeply with listeners. This emotionally charged song struck a chord with fans, and it became another #1 hit for Jennings, proving that he could seamlessly deliver rowdy outlaw anthems as well as poignant ballads, solidifying his reputation as one of country music’s most versatile and enduring artists.