Country music in 1999 looked a lot different from country music in the early 1960s, when Waylon Jennings began recording music under his own name. By the time the last year of the 20th century rolled around, Jennings was an icon who built his entire career on doing the opposite of what the music industry wanted or expected him to do. An entire subgenre of country music, outlaw country, centered around Jennings’ attitude and the attitude of his contemporaries, like Willie Nelson and Kris Kristofferson.
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Still, that’s not to say Jennings didn’t have opinions about what was going on in 1999—even if he did feel like an aged-out outsider.
Waylon Jennings Name-Drops His Favorite Country Acts From 1999
When you get three decades in the music industry under your belt, you tend to see an enduring act (or, conversely, a fleeting one) when you see it. Waylon Jennings had seen countless musical acts come and go over his 30+ years in the business, some of whom got their start before he did. Some left because they fell off the charts. Others tragically left this world altogether, like Jennings’ famous one-time bandleader, Buddy Holly.
By 1999, Jennings had also amassed his own list of personal favorite artists. “People like Andy Griggs, Leroy Parnell, Travis Tritt, I mean, them guys are here forever,” Jennings said during a fan Q&A portion of PrimeTime Country. “Mostly the women. I’m really impressed with them. Trisha Yearwood just kills me. She’s a great singer.” Around the time Jennings appeared on the popular television program, Yearwood was enjoying success on both the Billboard Hot 100 and Country charts with her 1999 track, “I’ll Still Love You More”.
The Outlaw Country Music Icon Felt Like an Outsider in the Industry
As younger and younger generations of country music artists began to enter the scene, acts like Waylon Jennings graduated to legacy status. In 1999, Jennings was sitting comfortably as an outlaw country pioneer whose longevity alone was enough to sustain his career. He was no longer the aspiring green musician he was in the late 1950s. But even then, Jennings didn’t have to go through what the country music artists of 1999 were going through, and that was just as well for the “Good Hearted Woman” singer.
“Being an artist anymore,” Jennings said while on PrimeTime Country. “You know…anything I say might sound like sour grapes. But I have my opinion ‘cause I’m looking at it [like an outsider]. I don’t understand some of it, you know. They got image consultants. Can you imagine me and Willie Nelson in the room? He’d come out without one. I’ve blown every image I ever had.”
Two decades after he started the outlaw country movement with his long-time friend and collaborator Willie Nelson, Jennings showed he still felt just as strongly about abiding only by his creative vision. He described receiving a message about coming down to a record label to discuss Jennings writing songs “that the record company wanted.” He continued, “Who cares about what the record company wants? They’re supposed to sell what you do.”
Photo by Paul Natkin/WireImage
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