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Readers’ Poll: The 10 Best Waylon Jennings Songs

From a TV theme song to an Outlaw anthem, your picks for the late legend’s greatest hits

Waylon Jennings

Waylon Jennings recorded some of Outlaw Country's most famous songs before his death in 2002.

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Worshipped as the patron saint of the perennially popular Outlaw Movement, Waylon Jennings helped turn staid Nashville on its head, carving his own path through label politics to bring a fresh energy and rock-edged sound to Music Row. Though he wore a black hat, he was truly one of music's good guys. Here's ol' Waylon's 10 Greatest Songs, as chosen by our readers. 

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10. “Amanda”

One month before the birth of his son Shooter, Jennings ducked into the recording studio to add different lyrics to "Amanda," a song he'd originally released five years prior. The new version — including the revised line "I got my first guitar when I was 14/Well, I finally made 40, still wearing jeans" — was included on 1979's Greatest Hits, a best-of compilation that unofficially capped the most successful decade of his career. Sung by a man who was still nose-deep in a crippling cocaine addiction, "Amanda" was soft and sweet, proof that even the roughest outlaws had a smooth side.

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9. “Theme From The Dukes of Hazzard (Good Ol’ Boys)”

As the narrator of CBS's 1979-85 hillbillies-in-hot-rods series The Dukes of Hazzard, Jennings set the stage every Friday night for Bo and Luke Duke's car-jumping adventures. It was also his voice singing the tailor-made theme song he wrote especially for the show. With Dukes proving popular, the parenthetically titled "Good Ol Boys" also took off on radio, racing to Number One on the country singles chart. While its lyrics obliquely referenced the law-bending main characters, Jennings wrote directly about his own below-the-neck appearances on the show in the final verse: "I'm a good ol' boy, you know my mama loves me/but she don't understand they keep a-showing my hands and not my face on TV." For such a hokey song, it was a glimmer of self-referential brilliance.

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8. “I’ve Always Been Crazy”

Released during the peak of his popularity, "I've Always Been Crazy" was a self-penned hit that doubled as both apology and defiant mission statement. The year was 1978, and Jennings — still reeling from a cocaine bust by the DEA — was tired of being the de facto spokesperson for a movement that grew out of the desire to gain artistic control, not media attention. This take-me-or-leave-me anthem set those frustrations to music. "I've always been crazy… nobody knows if it's something to bless or something to blame," he sang in the song's final verse, letting his own audience judge his fate. They responded by sending the album to the top of the country charts for two months.

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7. “Only Daddy That’ll Walk the Line”

Step off, honey. That's the gist of this 1968 bit of bravado, as Jennings tells a petulant woman to quit playing games or, rest assured, he will split. "When I start a-walkin', gonna hear you start a-squawkin', begging me to come back home," he sings. The song was among the first to foreshadow what would become Jennings' signature raw sound, less polished than his Nashville contemporaries. Full of swagger, "Only Daddy" even punctuated a key scene in this season's Mad Men, after an especially confident Don Draper crashes a meeting. Something tells us Draper and Jennings would have gotten along just fine.

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6. “Lonesome, On’ry and Mean”

You go ahead and tell Jennings that "ornery" isn't spelled that way. Though written by Steve Young, the pen behind the Eagles' evocative "Seven Bridges Road," "Lonesome, On'ry and Mean" became Jennings' theme song, summing up the way the seminal outlaw went through at least part of his career. Never released as a single, the song was the title track to his acclaimed 1973 album, as well as the lead-off track to 1979's multi-platinum Greatest Hits compilation. Covered by everyone from Travis Tritt to Dierks Bentley, "Lonesome, On'ry and Mean" remains testament to Jennings' wild, wandering and, at times, exhausted spirit. Listen to him sing the line "there's no escaping from his snowy white dream," and your own body will ache.

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

Jennings didn't play an actual gig in Luckenbach until July 4, 1997, two decades after he recorded this mid-tempo ballad about rekindling the flame in a small Texas town. That didn't stop him from turning the tune into a nostalgic, heartrending tribute to the simpler things in life, anchored by big, booming, baritone vocals and a tip of the cowboy hat to pre-outlaw pioneers like Hank Williams and Jerry Jeff Walker (who recorded a live album, Viva Terlingua, at the Luckenbach Dancehall in August 1973). Willie Nelson even got a piece of the action, singing the song's final verse while prepping fans for the Waylon and Willie album that would appear one year later.

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4. “Mammas Don’t Let Your Babies Grow Up to Be Cowboys”

If anyone was qualified to warn expectant mothers against the dangers of the rock & roll lifestyle, it was Waylon Jennings, who started making his living as a hard-living cosmic cowboy in the late 1950s. To strengthen the message, he teamed up with Willie Nelson to record this cautionary classic in 1978. Ed Bruce, the song's original writer, cracked the Top 20 in 1976 with his own version, but it was Jennings and Nelson's rendition that turned "Mammas" into a staple of outlaw-era country, leaving such a long, multi-faceted legacy that everyone from Black Lips to Alvin & the Chipmunks has since attempted to cover it. Oddly enough, Waylon's wife — fellow country rebel Jessi Colter — didn't take her husband's advice, leaving the couple's only son, Shooter Jennings, to launch his own career as a country singer two decades later. Whoops.

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3. “I Ain’t Living Long Like This”

Written by Rodney Crowell and recorded by Emmylou Harris, this live fast, die whenever anthem took on new energy when Jennings wrapped his rough-hewn baritone around it. While he may not have done exactly everything the lyrics talk about — although he did run afoul of the law in 1977 for cocaine possession —  Jennings sang it with such believability that one would believe he was a lifelong jailbird. The song further cemented his image as a badass and also gave him his 11th Number One country single. Today, "I Ain't Living Long Like This" remains a honky-tonk staple with artists from Justin Moore to Andy Griggs offering interpretations. Most recently, Vince Gill and Grand Ole Opry favorite Chris Janson performed it together on the Opry stage.

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2. “Honky Tonk Heroes”

Billy Joe Shaver may have written most of Honky Tonk Heroes, including the title track, but it was Waylon Jennings who injected the album with roughnecked, rocky-tonk attitude, bridging the gap between the rootsy twang of country music and the rule-breaking stomp of rock & roll. Jennings also threw a bone to his road band, the Waylors, who had been contractually blocked from performing on any of his RCA records previously. Fueled by the hard-won freedom to finally call his own shots — and, if the album's cover art is any indication, a good bit of alcohol — Jennings turned "Honky Tonk Heroes" into the mother of all outlaw country tunes, birthing an entire movement in three minutes and 36 seconds.

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1. “Are You Sure Hank Done It This Way”

Of all the songs Jennings has written, none has galvanized country fans quite like this one, which looks at country's changing sound through the eyes of its revered patriarch, Hank Williams. Whether it's a positive or negative view is open to debate. One on hand, the opening verse states the "same old tune, fiddle and guitar" needs a change, and asks "where do we take it from here?" But by the time Jennings sings "tell me one more time just so I understand, are you sure Hank done it this way?" there's a clear sense of "you gotta be shitting me" in his query. Progressive-minded artists favor the more benign interpretation — Keith Urban once projected a clip of Jennings singing the opening verse on his tour's jumbo screens — while country purists use the titular question to take genre-bending artists to task. Either way, it's a damn fine bit of writing.

In This Article: Waylon Jennings, Willie Nelson

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