Nashville never knew what to do with him or what to do about him. This one-time, disc-jockey refugee and bass player of Buddy Holly’s band who gave up his seat on that fateful plane ride to J.P. Richardson, the Big Bopper. He’d been in Nashville for almost ten years occasionally recording great songs like "Just To Satisfy You" and "Only Daddy That’ll Walk The Line," sometimes hitting the charts but basically going nowhere recording lots of what can charitably be called product until they let him do what he wanted. And he had to fight to do it. Even then it took that whole "Outlaw" thing to really get him noticed. It was bullshit of course. As Jennings said, "It was a good marketing tool." Or as George Jones told me at the time, "I think that’s just people talkin’ when they call it the Outlaw Movement or Progressive Country. I just think that’s people that love to dream up things and talk. Country music is country music."

Waylon Jennings, now that he’s gone, will forever be known as a country singer and he could sing country. He probably could’ve sung anything and sometimes did. What he really was however was a rocker disguised as a country singer. His best albums, a remarkable series of records starting with Lonesome On’ry & Mean in 1973 and continuing for the rest of that decade proves it. Whatever that magical thing is that makes certain singers great, Waylon had it to spare. He knew what he was singing about and sang with a quiet yet simmering intensity few possess. There was a soulful desperation in his voice that could draw you in and make you listen for hours. In his voice and also in his great band, The Waylors, was a restrained energy that threatened to explode but never did and it worked because the threat was enough.

Jennings was a master at slow ballads, such as "We Had It All" or Willie Nelson’s, "It’s Not Supposed To Be That Way." He had brilliant dynamics and an understanding of tension that could make an otherwise mundane line in a song totally dramatic. The second side of his album This Time is all slow ballads and he holds your attention for every second.

Even though in the country world he was a big star with 16 number one hits, I always felt he should’ve been bigger. For whatever reason he never really caught on with the audience attuned to "roots rock." Those who knew about him knew about him and it pretty much stayed that way his entire career. Jennings didn’t help matters with his somewhat legendary drug use and by the early ’80s when he should have been at the peak of his powers he began to fade artistically. His voice seemed weaker and it was obvious that he cared less about his albums leaning more towards songs that would continue to perpetuate his outlaw image instead of finding worthwhile material.

I only saw him perform a few times. Country music never really caught on in Philadelphia and only those artists who crossed over such as Willie Nelson would play the area frequently. The best time was in the mid-seventies when he appeared at the usually folk coffeehouse, the Main Point in the suburb of Bryn Mawr. Though Jennings later mentioned the show in a song, there weren’t many people in attendance, maybe 20 or 30, plus the members of Asleep at the Wheel who were appearing there the following night. The band was the classic version of the Waylors with Jennings' long-time drummer, Richie Albright, Donnie Brooks on harp and one of the true legends of the pedal steel, Ralph Mooney. Jennings, who was a big man, came out with his famous leather-coated Telecaster and proceeded to eye every woman in the place as he sang. He performed as if the small audience was in the hundreds, blowing minds with his trademark "chicken pickin’" lead guitar work. One of the most unacknowledged things about Waylon Jennings is that he was one of the great lead guitar players. The man not only knew what twang was all about, but he was funky, a Texas kind of funky.

About 12 years later I saw him again at a place that was usually a disco, again in the suburbs. (I don’t think Waylon Jennings ever performed within the city limits of Philadelphia.) His band was nowhere as good, with the keyboard player synthesizing the harmonica parts and the man on stage seemed a pale imitation of the one I’d seen before, dwelling more on the personae than the music.

In recent years, though he was plagued by illness—he couldn’t even walk on stage—he seemed revitalized and paying attention to the music. His albums started getting good reviews after years of mostly negative ones. He started doing new material including Dylan’s "Things Have Changed."

In 1993, RCA released a two-CD set, Only Daddy That’ll Walk The Line—The RCA Years that didn’t tell the whole story, leaving off some of his greatest songs. His masterpiece remains his album Honky Tonk Heroes which consists entirely of classic Billie Joe Shaver-penned songs except for the emotional closer, "We Had It All,"—perhaps Jennings' finest rendering of a ballad. On this and other albums recorded around that period such as Lonesome On’ry & Mean, This Time, Ramblin’ Man and Dreaming My Dreams you’ll find out why Waylon Jennings was not only a great country singer, but one of the great singers.

Related Stories:
Are There Any More Real Cowboys?
Interviews with Waylon Jennings and Willie Nelson.
By Jayson Whitehead
Nov '98

Just A Good Ol' Boy:
Waylon Jennings talks about Buddy Holly.
By Jayson Whitehead
Feb '99