Waylon Jennings
The Ramblin' Man

The context: Waylon Jennings first made waves as a professional musician in the late '50s, recording his debut single, "Jole Blon," with producer Buddy Holly and filling in as a bassist in Holly's band, The Crickets. (Jennings was supposed to be on the fateful flight that killed Holly in 1959, but gave up his seat to The Big Bopper.) By the late '60s, Jennings was a mid-level country singer working in the Nashville system, using the city's corps of proven session musicians on hits like "Walk On Out Of My Mind" and "I Got You." Jennings didn't become a superstar until he distanced himself from the country establishment a few years later, aligning with rebellious songwriters like Willie Nelson, Kris Kristofferson, and Billy Joe Shaver and making records with his live band, The Waylors. Beginning with the classic tandem of Lonesome, On'ry And Mean and Honky Tonk Heroes in 1973, Jennings' incredible run of '70s albums—including 1974's The Ramblin' Man—personified the burgeoning "outlaw" country sound.  


The greatness: The Ramblin' Man is typically regarded as a transitional work amid acknowledged masterpieces like Honky Tonk Heroes and This Time, also released in 1974 and made around the same time as The Ramblin' Man. By the time the blockbuster outlaw compilation Wanted! The Outlaws arrived in 1976, Jennings' and Nelson's unlikely triumph over Nashville's hostile indifference had been confirmed. But The Ramblin' Man sums up Jennings' appeal as well as any of his classics from the period, presenting 10 songs—mostly recorded over three days in July of '74—that weigh the pros and cons of being a hard-headed loner. While the iconic title track (a No. 1 country hit) might be Jennings' definitive tough-guy anthem, and the cover of The Allman Brothers Band's "Midnight Rider" reveals his Southern rocker side, The Ramblin' Man leans heaviest on weary ballads. Jennings might value his hard-won freedom, but on songs like "Rainy Day Woman" (featuring Ralph Mooney's astonishing steel guitar) and "Memories Of You And I," he surveys the damage it has wrought on his personal relationships. Fortunately, there's still room for hope: The album closes with the heartbreakingly sentimental "Amanda" (written by Bob McDill), where Jennings talks lovingly about a woman who accepts him for who he is, singing: "It's a measure of people who don't understand the pleasures of life in a hillbilly band / I got my first guitar when I was 14, well, I finally made 40, still wearing jeans."

Defining song: Jennings looks drunk, tired, and sweaty on the cover of The Ramblin' Man, like he was caught right after a three-hour show at some lowdown honky tonk on the wrong side of town. Similarly, "Memories Of You And I" sounds like it was a recorded after such a gig. A sweeping sigh of regret over leaving a lover for the road, "Memories Of You And I" is the flip-side of the strutting title song: "As the lines in my face grow deeper, and the well of my soul runs dry / I find that I drink more and more from the memories of you and I." The lyrics are dire, but the music is epic and romantic like a Sam Peckinpah western, showing Jennings' unique ability to simultaneously critique and glamorize his outlaw image.