Waylon Jennings wasn’t just a country music star—he was a renegade, a pioneer, and a voice that changed the landscape of the genre forever. With his deep, gravelly vocals and rebellious spirit, Jennings helped shape the “Outlaw Country” movement of the 1970s, challenging Nashville’s polished sound with a raw, authentic style that resonated with audiences far and wide. His music became the anthem of rebels, drifters, and dreamers, cementing his legacy as one of the most influential figures in country music history.

From chart-topping hits to soulful ballads, Jennings’ catalog is filled with unforgettable songs that still stir the hearts of listeners today. Whether you’re a lifelong fan or just discovering his music, this list of the top 10 most popular Waylon Jennings songs will take you on a trip through his legendary career. Get ready to dive into the tunes that defined a generation, blending hard-living lyrics with a sound that’s unmistakably Waylon. So grab your cowboy hat, turn up the volume, and let’s explore the timeless tracks that made Waylon Jennings a true outlaw legend!

1. “Amanda” (1974)

“Amanda” first appeared on Jennings’ 1974 album The Ramblin’ Man, but it wasn’t released as a single until 1979, when it became a major hit. The song is a tender ballad, showcasing a softer, more sentimental side of Jennings. Written by Bob McDill, the lyrics express deep admiration and love for a woman named Amanda, portraying her as the grounding force in the narrator’s life. Jennings’ heartfelt delivery, paired with the song’s gentle melody, makes it one of his most beloved tracks. The simplicity and sincerity of “Amanda” have made it a timeless country love song, resonating with fans long after its initial release.

2. “The Wurlitzer Prize (I Don’t Want to Get Over You)” (1977)

Released in 1977, “The Wurlitzer Prize (I Don’t Want to Get Over You)” is a melancholic yet captivating song that showcases Jennings’ ability to convey deep emotion with restraint. Written by Chips Moman and Bobby Emmons, the song features a simple, piano-driven melody that complements Jennings’ smooth, understated vocal performance. The lyrics speak to the pain of a love lost and the temptation to drown those sorrows in a barroom jukebox. The song became a No. 1 hit and was one of the standout tracks on Waylon & Willie. Its gentle, mournful tone set it apart from the rowdier songs of the Outlaw Country era, proving Jennings’ versatility as a performer.

3. “Only Daddy That’ll Walk the Line” (1968)

Released in 1968, “Only Daddy That’ll Walk the Line” was one of Waylon Jennings’ early breakthrough hits. The song features a driving beat and catchy rhythm, blending traditional country sounds with a rebellious rock influence. The lyrics describe a man who stands his ground in a tumultuous relationship, making it a perfect fit for Jennings’ tough, no-nonsense persona. The song reached No. 2 on the country charts and helped establish Jennings as a rising star in the Nashville scene. It also foreshadowed the direction his music would take as he became a leader in the Outlaw Country movement, pushing against the constraints of the country music establishment.

4. “Lonesome, On’ry and Mean” (1973)

“Lonesome, On’ry and Mean” is one of the defining tracks of the Outlaw Country movement. Released in 1973, the song’s gritty lyrics and rugged sound struck a chord with fans of the genre who were tired of the polished, formulaic country music coming out of Nashville. Written by Steve Young, the song tells the story of a restless, wandering man who struggles to find peace. Jennings’ raw, powerful delivery perfectly captures the sense of isolation and defiance at the heart of the song. It became the title track to one of Jennings’ most influential albums and solidified his reputation as a trailblazer willing to challenge the status quo.

5. “Rainy Day Woman” (1974)

Released in 1974 as part of the The Ramblin’ Man album, “Rainy Day Woman” is a rollicking, upbeat track that showcases Jennings’ talent for blending traditional country with rock influences. The song’s infectious rhythm and playful lyrics tell the story of a man who’s always getting into trouble with women but can’t seem to stay away. Jennings’ charismatic performance and the song’s energetic arrangement make it an undeniable crowd-pleaser. “Rainy Day Woman” became a Top 5 hit on the country charts and is still one of Jennings’ most fun and memorable songs, highlighting his ability to balance humor and heart in his music.

6. “Luckenbach, Texas (Back to the Basics of Love)” (1977)

Released in 1977, “Luckenbach, Texas (Back to the Basics of Love)” is one of Waylon Jennings’ most celebrated songs. It’s a poignant anthem that taps into the yearning for simplicity amidst the complexities of life. Written by Bobby Emmons and Chips Moman, the song channels a sense of nostalgia for a time when life was less complicated, using the small Texas town of Luckenbach as a metaphor. The song’s minimalist country sound, combined with Jennings’ rich baritone, creates a warm, wistful atmosphere. Its chorus, “Let’s go to Luckenbach, Texas, with Waylon and Willie and the boys,” cemented the track as a cultural touchstone, enamoring fans with its laid-back, back-to-roots vibe. It became a No. 1 hit on the country charts and is still a fan favorite today, symbolizing the Outlaw Country movement’s desire to break free from the constraints of the Nashville establishment.

7. “Good Hearted Woman” (1972)

“Good Hearted Woman”, first released in 1972, holds a special place in Waylon Jennings’ discography. Co-written with Willie Nelson, the song tells the story of a woman who stands by her man despite his rough-around-the-edges lifestyle. The lyrics, filled with warmth and gratitude, are a love letter to the strong, devoted women who support their partners unconditionally. In 1975, a duet version of the song was released on the album Wanted! The Outlaws, which became the first country album to be certified platinum. Jennings’ rugged voice paired with Nelson’s distinct delivery made the track a standout, and it resonated deeply with fans, particularly those who admired the rebellious spirit of the Outlaw Country movement. The song became a Top 10 hit and is still regarded as one of Jennings’ signature tunes.

8. “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” became an instant classic. This cautionary tale, written by Ed and Patsy Bruce, warns mothers to steer their sons away from the roaming, rugged life of a cowboy. The song’s playful yet heartfelt lyrics perfectly capture the romanticized yet challenging existence of cowboys, a metaphor for the rebellious country lifestyle Jennings embodied. The duet with Willie Nelson elevated this track to legendary status, blending their contrasting voices in perfect harmony. The song topped the country charts and became a Grammy Award-winning hit, solidifying both Jennings and Nelson as leading figures in the Outlaw Country movement.

9. “Are You Sure Hank Done It This Way” (1975)

“Are You Sure Hank Done It This Way” is a bold critique of the commercialization of country music, released in 1975 on the Dreaming My Dreams album. In this track, Jennings questions whether the genre’s pioneers, like Hank Williams, would approve of the slick, polished direction country music was heading in. Jennings masterfully blends a rebellious attitude with respect for the roots of country music, making this song both a tribute and a call to action. The gritty guitar riffs and raw vocals reflect the frustration many Outlaw Country artists felt at the time, as they sought to reclaim the authenticity of the genre. This track became a No. 1 hit on the country charts and remains a defining moment in Jennings’ career.

10. “I’ve Always Been Crazy” (1978)

Released in 1978, “I’ve Always Been Crazy” is a deeply personal track from Jennings, reflecting his self-awareness and acceptance of his wild lifestyle. The song is a declaration of his refusal to conform, with lyrics that highlight both the highs and lows of being an outlaw in country music. The driving rhythm and Jennings’ soulful delivery give the song an edge, while the introspective lyrics provide a glimpse into the man behind the outlaw persona. The track became a No. 1 hit on the country charts and is often seen as an anthem for those who proudly live outside societal norms. It’s a standout example of Jennings’ ability to blend vulnerability and defiance in his music.