The path to becoming a well-versed, know-it-all country stan seems pretty exhausting, and as we mentioned in the first part of this series, we’re here to help you get a head start. First, we discussed the eighties, a melting pot of traditional, progressive, and iconic sounds that is easy enough for modern fans to digest and helped shape many of today’s country standards. Now, it’s time to turn the spotlight toward some of country’s greatest outliers: the outlaws.
In the country sphere, the term “outlaw” can refer to a few different things. More broadly, it describes artists who pushed against the genre’s norms and challenged the Nashville establishment. The “Outlaw Movement,” however, refers to a more specific shift led by artists like Willie Nelson and Waylon Jennings, who fought for greater creative control rather than being puppeteered by their labels. Its roots can be traced back to the late sixties, and its influence has continued to shape a broader strain of country music over the decades. For the sake of this series, we’ll focus on three classic albums released between the late sixties and early eighties that helped define this rebellious side of country music and remain influential today.
Willie Nelson – Shotgun Willie
While today’s listeners may see Willie Nelson as pop culture’s stoner grandpa, there’s much more to the braided legend than meets the modern eye. Constantly getting himself in and out of trouble, Nelson seemed to be up against the whole world during his prime. After leaving RCA Records, he recorded Shotgun Willie. Released during the early stages of his scruffy-beard-and-long-hair era, the record cemented both his image and his sound, helping establish him as one of the leading figures of the outlaw movement. The title track and cover art especially helped paint the new persona, attaching his name to an image.
This album included the timeless “Sad Songs and Waltzes,” which has been covered numerous times by artists such as Keith Whitley, Cody Johnson, Ernest Tubb, and even CAKE. “Devil in a Sleepin’ Bag” showed Willie’s freedom to write about whatever caught his attention. The song tells the story of his friend and drummer Paul English’s uncomfortable tour bus sleeping arrangements. Fully separated from the standardized “Nashville Sound,” Shotgun Willie wasn’t just a career success. It was the beginning of a whole wave of era-defining nonconformists who had their own way of doing things. Not to mention, it included “Whiskey River,” one of Nelson’s biggest hits and a staple of his live shows.
Hank Williams, Jr. – Habits Old And New
Looking at the legacy Hank Williams Jr. has created, rebellion is perhaps the most foundational element of it all. Growing up, Jr. was more of a tribute act, doing cover shows with his late father’s material. Stepping out of Sr.’s shadow, Hank finally debuted his own original work, showcasing a brash, larger-than-life personality that had been living beneath the surface. His album, Habits Old And New, showcased some of his most defiant work, with plenty of flavor as he sang a mix of his most controversial yet iconic songs to date. Songs like “Old Habits” and “The Blues Man” showed a more serious, vulnerable Hank, while “Dinosaur” and “The American Way” presented him as an untameable wildcat set in his ways.
Today, these songs remain relevant in country music, not only as fan favorites but also as influential pieces of country music history that paved the way for some of the rowdiest generations to follow.
Waylon Jennings – Dreaming My Dreams
If there’s a song that captured the thesis of the Outlaw Movement, it was Waylon Jennings’s “Are You Sure Hank Done It This Way.” Jennings points out the irony of an industry that held Hank Williams Sr. up as the standard while following its own inauthentic, cookie-cutter formula. This track was included on his 1975 album, Dreaming My Dreams, alongside many other standouts like “Bob Wills Is Still the King” and the rambunctious “Waymore’s Blues,” which showed more of Waylon’s wild attitude.
This record took place at the height of Waylon’s artistic freedom. Thanks in part to Willie Nelson’s departure from RCA, the label was more willing to negotiate with Waylon Jennings a few years before this release, giving him much more leverage and room to breathe. By selecting each song and the musicians who played on his records, he made moves that went against industry norms and ultimately laid the groundwork for country music. Dreaming My Dreams is one of the greatest results of that transformation.
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Today, plenty of artists still roam under the outlaw umbrella. Folks like Benjamin Tod, Charley Crockett, Sierra Ferrell, and Cody Jinks fit the description through their unconventional ways while still carrying on certain stylistic elements of the artists who carved out the path before them. Reflecting on albums like Shotgun Willie, Habits New And Old, and Dreaming My Dreams, it’s apparent that some of the best art is made with no restrictions. As far as a good introduction to outlaw music goes, Willie, Waylon, and Hank Jr. have you covered.
