Top Ten Songs by Waylon Jennings

The late Waylon Jennings, who passed away in 2002, was one of the pioneers of country music. Jennings combined his country roots with rock ‘n roll training from Buddy Holly and his own entertaining, if troubled, personal life to create the “outlaw” movement in country music. Jennings, followed by country luminaries including Johnny Cash and Willie Nelson (who, along with Kris Kristofferson, would join Waylon in the legendary Highwaymen), took music away from Nashville and infused country music with new spirit, new influence, and new style.

In Jennings’ honor, we now present an extraordinarily subjective list of his ten greatest songs, in reverse order:

10. Theme From the Dukes of Hazzard (Good Ol’ Boys)

“Good Ol’ Boys” makes the list not for any sort of musical brilliance, but because it arguably became his best-known song, though certainly not his best song. The theme from the CBS show “Dukes of Hazzard” (for which Jennings also acted as narrator) was played for millions of Americans each week, many of whom were unfamiliar with Jennings’ music. While some of Jennings hits from the 1970s, such as “Luckenbach, Texas” and “Amanda” did make the pop charts, “Dukes of Hazzard” undoubtedly gave Jennings his largest amount of national exposure.

As a song, “Good Ol’ Boys” was a good fit for the show: simple, fun, and unsophisticated. It cannot compare with the soul or the talent of many of Waylon’s other works, but given its notoriety, the theme from the “Dukes of Hazzard” slides into the tenth spot on the list.

9. Only Daddy That’ll Walk The Line

First released on 1967’s “Only The Greatest”, Jennings’ “Only Daddy…” was the first cut of the album, and one of the first glimpses of Jennings’ move away from more traditional Nashville-based country sounds (such as Waylon Sings Ol’ Harlan, released earlier that year). The distinctive opening bass line was reminiscent of 1950s blues and rock, while Waylon’s voice blends seamlessly into one of his greatest tunes.

“Only Daddy…” also displays the roots of Waylon’s “outlaw” attitude. Defiant and soulful, this song was the beginning of the Waylon of the 1970s: irreverent, arrogant, talented, and dark.

8. This Time

A milder, if still defiant, Waylon Jennings shines through on “This Time,” Waylon’s first number one single (off the 1974 album of the same name). With a wailing harmonica and poetic lyrics (written by Waylon himself), “This Time” is beautiful in its simplicity, both in music and in theme. Even while showing off his, ahem, sensitive side, Jennings remains in control, reminding his partner, “You’re gonna have to toe the mark and walk the line.”

7. Rainy Day Woman

While not a number-one hit (in fact, “I’m A Rambling Man” was a bigger hit off the same album), “Rainy Day Woman” belongs any list of essential Waylon Jennings songs. The high-pitched, quick-picked guitar is a direct result of Buddy Holly’s influence, and the result is one of Jennings’ most distinctive songs. The lyric “sure as hell looks just like rain” was a dangerous choice in an industry which 20 years later still would censor the word “hell” in Randy Travis’ “The Hole”.

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

Recorded during the prime of his career, this number one hit released in 1976, is a country music classic. Jennings’ voice is never better than in the opening two lyrics, sung nearly a capella: “The only two things in life that make it worth livin’/Is guitars tuned good and firm feelin’ women”.

A soft, simple melody frames Jennings voice perfectly; the result is a profound, humble paean to self-reliance and a warning of the dangers of success. A guest appearance by old friend Willie Nelson is a perfect ending to a song that remains, and will forever remain, a country music classic.

5. Are You Sure Hank Done It This Way

Jennings puts his anti-Nashville feelings to words in his 1975 chart-topper “Are You Sure Hank Done It This Way” off the aptly titled LP “Dreaming My Dreams”. A hard-driving bass line and a rebellious attitude toward the Nashville establishment – “We’ve been the same way for years/We need to change” – are signatures of Waylon’s career, and fully on display in “Are You Sure…”

4. Lonesome, On’ry And Mean

Perhaps Jennings’ angriest song – and definitely his darkest hit – “Lonesome” was the title track of a 1973 album, then re-released on “Greatest Hits” in 1979. The “Lonesome” LP was Jennings’ first under a new contract, and reflected his first break from the Nashville sound toward his unique blend of rock, country, hillbilly, and folk, a blend on display in this classic road song. While neither the album, nor the song, were a major hit, the song and album “Lonesome, On’ry And Mean” were a major step toward Jennings’ move from a clean-shaven, producer-led Nashville artist to the bearded, road-weary, hell-bent outlaw described in the song. Along with “Are You Sure Hank Done It This Way”, “Lonesome…” is one of Waylon’s best road songs, one of his most distinctive hits, and a key song in the revolution of country music in the 1970s.

3. Good Hearted Woman

Waylon’s first number one duet with Willie Nelson, 1975’s “Good Hearted Woman” is another of Waylon Jennings’ – and country music’s – all-time great songs. Simple, poignant, and somehow heartening, “Good Hearted Woman” is country music at its best.

“Good Hearted Woman” was released on “Wanted! The Outlaws”, a compilation that propelled both Waylon Jennings and Willie Nelson into the country music spotlight. While Jennings would later dispute the “outlaw” label, “Good Hearted Woman” and the ballad “My Heroes Have Always Been Cowboys” led “Wanted!” to the top of not only the country charts but the pop charts. The success of the album put Jennings squarely in the spotlight and opened the most successful portion of his career, both artistically and financially.

2. Mamas Don’t Let Your Babies Grow Up to Be Cowboys

Another duet with Willie Nelson, “Mamas…” is a sorrowful ballad, an ode to the cowboy life, sung by two artists often referred to as the last of the true cowboy singers. Released on 1978’s “Willie and Waylon,” this song marks the end of an era both for America and for country music at large. One of Waylon’s biggest hits, it won him his second Grammy and led “Willie and Waylon” to the number one spot on the Billboard Country chart.

1. I’ve Always Been Crazy

To be sure, trying to pick the single greatest song by Waylon Jennings is a futile, subjective, and argumentative task. Given the range of his songs, the varying styles used, and the remarkable success he enjoyed over more than forty years in music, it’s a fool’s game to pick one song. But, if there is any one song that showcases Jennings at his absolute best, and which captures him perfectly, “I’ve Always Been Crazy” should get the nod.

Musically, “I’ve Always Been Crazy” may be the best example of Jennings’ versatility as a songwriter and as a singer. “Crazy” uses the standard hard-charging bass line, this time combined with piano, along with a long instrumental break which showcases Jennings’ guitar-picking skills. Jennings’ vocals are spectacular, as usual, and the song’s coda even features horns, unusual for Waylon’s music.

But it’s the attitude of “Crazy” that makes it Jennings’ greatest song. The lyrics capture Jennings’ stubborn, irreverent personality; “I’ve always been crazy/But it’s kept me from going insane” is the perfect couplet for a man who lived the life about which he sung.

To be sure, “Crazy” was a number one hit, though not Jennings’ biggest-selling album. But “I’ve Always Been Crazy”, a tune written when Jennings was at the peak of his career, is our choice as Waylon Jennings’ greatest song of all time. Disagree? Check out the “comments” section below and make your voice heard!

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