Waylon Jennings began performing professionally in the late 1950s, but it wasn’t until he freed himself from the shackles of Nashville in the 1970s that he became a star. With his gruff baritone, rock and roll infused honky tonk, leather jackets, and rebellious attitude, Jennings personified the outlaw country movement more than any other performer. Despite experiencing a slump in sales in the latter half of his career, Jennings remained a huge live draw right up until his death in 2002, a superstar until the very end. Here, we take a look back at some of his finest moments with our pick of the 20 best Waylon Jennings albums.
20. What Goes Around Comes Around
After the outlaw movement took off in the early 1970s, Jennings became white-hot. His singles were charting in the top ten (and predominantly at number one) and his albums were chart-toppers. But by 1979, the music landscape had moved on. With interest waning, What Goes Around Comes Around became his first album since 1975 not to hit the No. 1 spot (although it still managed to spend 14 weeks at number 2). But while his hot streak may have been coming to an end, it’s still a gorgeous album, with Jennings’ rough baritone adding a raw earthiness to even the most sweetly sentimental ballad.
19. Closing In On The Fire
If Jennings’ hot streak was on its last legs by the end of the 1970s, it was nothing but a distant memory by 1995. But only a fool would dismiss late-career offerings like Closing In On The Fire, a fabulous album that shines a spotlight on Jennings’ weathered but still powerful vocals and superlative songwriting talents. Guest appearances from the likes of Mary Stuart, Mark Knopfler, and Sheryl Crow are a nice touch, but not strictly necessary – Waylon is, as ever, the star of the show. The album, which reached number 71 on the country charts, was the final studio album ever released by the singer before his death in 2002.
Sonically, Folk-Country is a world away from the sound that would turn Jennings into one of country’s biggest stars in the 1970s. Determined to fashion Jennings into a traditional country star in the style of Patsy Cline or Jim Reeves, producer Ched Atkins polished up his rough edges, toned down his earthy quality, and bought his assertive masculinity down a few notches. The result might not be the Waylon we know best, but it’s still wonderfully listenable, particularly on stand-out tracks like Man of Constant Sorrow and Harlan Howard’s Another Bridge to Burn.
17. Good Hearted Woman
In 1972, Jennings released two albums that helped transform him from a talented but standard issue country star into one of the pioneers of the outlaw movement. The first was Good Hearted Woman. Described by All Music as “a pretty sensational outing for Jennings” in which the singer is “feeling his power,” the album was greeted warmly by fans, who appreciated Jennings’ new, looser style enough to send the album to number 7 on the country charts.
16. Hangin’ On
There’s a couple of skippable songs on 1968’s Hangin’ On, but the quality of most of the material songs is so high, it’s almost impossible to care. Buoyed by the success of the top ten hit single, The Chokin’ Kind, the album was a commercial success, peaking at number 9 on the country charts.
15. I’ve Always Been Crazy
The outlaw country movement may have turned Jennings into a megastar, but being a permanent fixture on the country charts comes with a downside – attention. By 1978, Jennings was sick of the attention, sick of the hype, sick of how Nashville was cashing in on the success of the movement, and sick of being splashed across the front pages (although in fairness, his spiraling cocaine addiction and frequent drug busts were responsible for more of the headlines than his music). I’ve Always Been Crazy was his middle-fingered salute to the madness. Caustic, wryly humorous, and full of piss and vinegar, it spent almost a year floating around the charts after hitting the top spot.
14. Just to Satisfy You
Jennings closed out the 1960s on a high note with the excellent Just to Satisfy You. The standout song is the title track, a highly enjoyable country/ rockabilly mash-up written by Jennings and Don Bowman. It’s been covered on numerous occasions since (most notably by Glen Campbell), but never performed quite so well as it is here. Released in March 1969, the album reached number 7 on the Billboard country albums chart.
13. Love of the Common People
In his autobiography, Jennings called the title track to his 1967 album, Love of the Common People, one of his favorite songs, writing, “It had it all, the horn stabs that I loved so much, an insistent piano figure that lodged in your brain, and four (count ’em) key modulations upward, so the song never stopped getting you higher. The lyrics were especially meaningful, for a poor country boy who had worked his way up from ‘a dream you could cling to’ to a spot in the working world of country music.” The rest of the album isn’t exactly shoddy either, with Jennings’ innovative covers of Mel Tillis’ Ruby Don’t Take Your Love to Town and the Beatles’ You’ve Got to Hide Your Love Away standing out as highlights.
12. Singer of Sad Songs
By 1970, Jennings’ relationship with Nashville was at breaking point, and on Singer of Sad Songs, his bubbling discontent is obvious. In its offbeat selection of unconventional covers (including a blazing version of the Rolling Stones’ Honky Tonk Woman and a lovely rendition of Tim Hardin’s folky classic, If I Were a Carpenter), vigorous energy, and layered guitars, the wind of change can be smelt. Annoyed at Jennings’ decision to record only the title track in Nashville, RCA Records refused to promote the album, resulting in it stalling at number 23 in the charts – Jennings’ lowest position since 1967.
11. Ol’ Waylon
Released in April 1977 at the very peak of his fame, Ol’ Waylon became Jennings’ fourth consecutive chart-topper, spending 13 weeks at number one and becoming the first country album by a solo artist to certify platinum. The massively successful Luckenbach, Texas (Back to the Basics of Love) gets most of the attention, but the rest of the album deserves just as much glory, with This is Getting Funny, If You See Me Getting Smaller, and Lucille all deserving a revisit.
Jennings kicked off the 1970s in style with Waylon. It’s best remembered for the rollicking cover of Chuck Berry’s Brown Eyed Handsome Man, which soared to number 3 on the charts. The real star, however, is his version of Mickey Newbury’s The Thirty-Third Of August, a gorgeously layered, wonderfully textured slow burner that whispers of the change in musical direction that would become ever more apparent over his next few releases.
9. Are You Ready For Country
The outlaws always had more in common with rock stars than traditional country singers, so it was almost inevitable that at some point, they’d cross the line and start singing the songs that went with their image. In 1976, Jennings did just that with Are You Ready For Country, a collection of rock-orientated songs that takes its title from a Neil Young song (which Jennings does a blazing cover of) and includes tracks by everyone from Dr. Hook and Jimmy Webb to the Marshall Tucker Band. It may be a step outside Waylon’s comfort zone (and probably the listeners too), but it’s still outstandingly entertaining.
8. Waylon Sings Ol’ Harlan
As Pop Matters notes, Harlan Howard is rightly considered one of country music’s greatest songwriters ever, and on the wonderful Waylon Sings Ol’ Harlan, Jennings brings the dark vision of his songs to life. “Harlan was everybody’s friend…I was writing more and more, and Harlan talked to me continually about the craft, giving me advice,” Jennings later said. His admiration for the writer led him to cover over 70 of his songs during his career, but here, he’s cherry-picked the best, with the slyly humorous Sunset and Vine and heartbreaking Beautiful Annabel Lee standing out as highlights.
7. Wanted! The Outlaws
In 1975, Jennings teamed up with fellow outlaws Willie Nelson, Jessi Colter, and Tompall Glaser for Wanted! The Outlaws. Released at the very peak of the movement’s fame, it became a huge crossover hit, reaching number 1 on the country charts and number 10 on the pop charts. Within just a few months of its release, it made history by becoming the first-ever country album to be certified platinum after selling over one million units. Keys tracks to take for a whirl include Suspicious Minds and Good Hearted Woman, which reached number 2 and number 1 in the charts respectively.
6. The Ramblin’ Man
By the time he came to release The Ramblin’ Man in 1974, Jennings had fully embraced the outlaw movement. The album may be a little glossier and more commercial than its direct predecessors, but the diverse song list, raucous sound, and earthy vocals are as untamed as you’d expect from country’s unruliest maverick. As countrythangdaily.com notes, the solid tempo and infectious guitar work make the title track (and No. 1 single) a particular highlight, but the heartbreaking Amanda and lovely Oklahoma Sunshine also deserve a mention.
5. The Taker/ Tulsa
As atthebarrier.com writes, in contrast with some of his earlier albums, it’s clear that Waylon was calling the shots with regard to material on his 1971 album, The Taker/ Tulsa. The diverse tracklist, which includes four Kris Kristofferson compositions, highlights Jennings’ increasing frustrations with the constraints of Nashville and his first steps on the path to becoming an outlaw. Chief highlights include the wonderfully gentle Lovin’ Her Was Easier (Than Anything I’ll Ever Do Again) and the poignant cover of Bobby Bond’s anti-war song, Six White Horses.
4. This Time
The topics on This Time are typical of most of Jennings’ material: songs about the West and outlaws and women. But while the subject matter might be basic, Jennings’ delivery is transformative. Even on the songs penned by other writers (four of the ten songs were written by Willie Nelson), Jennings’ soulful performance and ability to get inside the lyrics makes them his own.
3. Dreaming My Dreams
Jennings’ twenty-second studio album was a critical and commercial sensation, becoming his first album to go gold and earning him the award for Male Vocalist of the Year by the Country Music Association. Described by Billboard as a “solid mix of ballad and rockers, some straight country and lots that cannot be classified,” the album showcases Jennings’ talents as an interpreter, a writer, and a singer, delivering passion, humor, and tenderness in equal measure.
2. Lonesome, On’ry and Mean
In 1972, Jennings negotiated a deal with RCA that gave him the freedom to produce his own records whenever he wanted. The first result of the deal was Lonesome, On’ry and Mean, an album that All Music describes as the “quintessential Waylon Jennings outlaw record.” Produced by Jennings and his band, it’s an electrifying set that jumps from rock and roll to country, folk to honky tonk with effortless grace. Released in March 1973, it became one of his biggest hits till that point, peaking at number 8 on the country charts.
1. Honky Tonk Heroes
On Honky Tonk Heroes, Jennings’ revived honky tonk, thrust the outlaw moment into the limelight, and established himself as one of country music’s biggest stars. He also made an album that, almost 50 years after its release, is still considered one of the most influential recordings in music history. Described by Billy Joe Shaver (who wrote or co-wrote every track on the album) as “the touchstone of the Outlaw movement,” it takes risks and plays around with genres so compellingly, even people with no time for country music can’t help but be enthralled by it.