Waylon Jennings wasn’t just a country music singer—he was a legend, a rebel, and one of the driving forces behind the outlaw country movement. With his deep, rugged voice and a sound that broke away from the polished Nashville formula, Jennings carved out a legacy that still resonates with country fans today. His music wasn’t about following the rules; it was about telling raw, honest stories of love, loss, freedom, and the road-worn life of a true outlaw.
From heartfelt ballads to foot-stomping anthems, Jennings’ catalog is packed with unforgettable songs that defined a generation of country music. Whether he was singing about the wild spirit of cowboys, the struggles of a rambling man, or the simple joys of small-town life, his music spoke to the soul of America. His collaborations with Willie Nelson, Johnny Cash, and other legends only cemented his status as one of country’s greatest icons.
In this list, we’re diving into the top 10 most popular Waylon Jennings songs of all time—the tracks that shaped his career and continue to inspire musicians and fans alike. Get ready to take a trip through some of the greatest outlaw country songs ever recorded. 🎸🔥
1. “Mammas Don’t Let Your Babies Grow Up to Be Cowboys” (1976)
Originally penned by Ed and Patsy Bruce, “Mammas Don’t Let Your Babies Grow Up to Be Cowboys” first appeared on Ed Bruce’s 1976 album, but it was Waylon Jennings and Willie Nelson who turned it into a country music classic. Their duet, released on the 1978 album Waylon & Willie, became an anthem of the outlaw country movement. The song tells the story of a mother’s warning about the lonely, rugged life of a cowboy—a life filled with hardship, wandering, and emotional distance. While it cautions against the cowboy way, the song also carries a sense of admiration for those who embrace it. Jennings and Nelson’s unmistakable harmonies, combined with their laid-back yet soulful delivery, struck a chord with fans. Their version soared to No. 1 on the country charts, further solidifying their status as legends. The song has since been covered multiple times and remains one of the defining tracks of outlaw country.
2. “Luckenbach, Texas (Back to the Basics of Love)” (1977)
Written by Chips Moman and Bobby Emmons, “Luckenbach, Texas” became one of Waylon Jennings’ most beloved hits upon its release in 1977. The song tells the story of a couple lost in material wealth and societal pressures, longing to return to a simpler, more authentic way of life. With references to country greats like Hank Williams and a spoken cameo from Willie Nelson, the song perfectly captures the anti-establishment spirit of the outlaw country movement. Jennings’ deep, gravelly voice gives the lyrics a nostalgic yet rebellious feel, making it a song that resonated with anyone who had ever dreamed of escaping the rat race. It quickly became a country anthem, spending weeks at No. 1 and cementing itself as one of Jennings’ signature songs.
3. “Good Hearted Woman” (1972)
Inspired by an ad about Tina Turner, Waylon Jennings and Willie Nelson co-wrote this classic country tune, celebrating a strong woman who remains loyal to her free-spirited, sometimes reckless man. Jennings originally recorded it solo in 1972 for his album Good Hearted Woman, but it was the 1975 duet with Nelson—featured on the compilation Wanted! The Outlaws—that became legendary. The song’s catchy melody and heartfelt lyrics resonated deeply with fans, making it a defining track of the outlaw country era. It tells a story of love, patience, and devotion despite life’s ups and downs, making it relatable to countless listeners. Today, it remains one of Jennings’ most enduring and frequently played songs.
4. “Are You Sure Hank Done It This Way” (1975)
From the album Dreaming My Dreams, this song is a sharp critique of the evolving country music industry. Jennings questions whether modern artists have strayed too far from the raw, authentic style of Hank Williams, lamenting the polished, commercialized Nashville sound. The track’s gritty lyrics and driving beat reflect Jennings’ frustration with the mainstream country scene, making it an anthem for the outlaw movement. Fans embraced its rebellious energy, and it became one of Jennings’ most influential songs, inspiring future generations of country artists to stay true to their roots.
5. “I’ve Always Been Crazy” (1978)
This introspective song serves as a personal anthem for Waylon Jennings, reflecting on his rebellious nature and the highs and lows of his life. Released in 1978 as the title track of his album, the song blends humor with honesty, acknowledging both the struggles and the joys of living by one’s own rules. Jennings’ distinctive voice, paired with the song’s smooth yet defiant melody, made it an instant favorite among fans. Its introspective lyrics gave listeners a glimpse into the mind of a man who had walked his own path, regardless of the consequences. It remains one of his most celebrated tracks, encapsulating his fearless, unapologetic spirit.
6. “Theme from The Dukes of Hazzard (Good Ol’ Boys)” (1980)
Perhaps one of Waylon Jennings’ most widely recognized songs, this track served as the theme song for the hit television show The Dukes of Hazzard. Released in 1980, it perfectly captured the show’s rebellious, fun-loving, and Southern spirit. With its laid-back rhythm and Jennings’ rich, deep vocals, the song became an instant classic. Not only did it reach No. 1 on the country charts, but it also became deeply ingrained in pop culture. Even today, hearing the first few notes instantly brings back memories of fast cars, country roads, and the outlaw charm of The Dukes of Hazzard.
7. “Amanda” (1974)
Originally written by Bob McDill and first recorded by Don Williams, Waylon Jennings brought new life to “Amanda” when he recorded it for his 1974 album The Ramblin’ Man. The song is a tender, reflective ballad about a man acknowledging how his wild ways may have been unfair to the woman who loved him. Jennings’ gravelly voice adds depth and sincerity to the song’s wistful lyrics, making it one of his most touching performances. When re-released as a single in 1979, it quickly soared to No. 1 on the country charts, becoming one of his most cherished recordings. The song remains a timeless classic, loved for its heartfelt emotion and simple yet powerful storytelling.
8. “Only Daddy That’ll Walk the Line” (1968)
One of Jennings’ early hits, this energetic track was released in 1968 on his album Only the Greatest. Written by Ivy J. Bryant, the song features a bluesy, honky-tonk sound with a driving beat that perfectly showcases Jennings’ evolving musical style. The lyrics tell the story of a man stuck in a demanding relationship, yet remaining the only one willing to stick around. The song’s fiery attitude and electric guitar riffs helped establish Jennings’ presence in the country music world before he fully embraced the outlaw movement. It remains a standout in his early catalog.
9. “I Ain’t Living Long Like This” (1979)
Originally written and recorded by Rodney Crowell in 1978, Waylon Jennings made this song his own when he included it on his 1979 album What Goes Around Comes Around. The lyrics tell the story of a man living on the edge, caught up in a life of crime, danger, and reckless decisions. Jennings’ raw, urgent vocals and the song’s hard-driving rhythm made it an instant outlaw anthem. The track resonated with fans who admired Jennings’ unfiltered honesty, reflecting his own struggles with substance abuse and run-ins with the law. It remains one of his most powerful and electrifying performances.
10. “Highwayman” (1985)
One of the most legendary country collaborations of all time, “Highwayman” was written by Jimmy Webb and recorded by The Highwaymen—Waylon Jennings, Willie Nelson, Johnny Cash, and Kris Kristofferson—in 1985. Each member took a verse, portraying different incarnations of a wandering soul: a highwayman, a sailor, a dam builder, and a starship pilot. Jennings’ deep, commanding voice added gravity to the song’s powerful storytelling. The track became the signature song of the supergroup, topping the country charts and leaving a lasting legacy. It remains one of the most iconic recordings in outlaw country history, cementing the legends of the men who sang it.
Samuel Moore is a frequent contributor to Singers Room. Since 2005, Singersroom has been the voice of R&B around the world. Connect with us via social media below.
