Waylon Jennings: The Eternal Outlaw

“He was left at the studio to record Honky Tonk Heroes by himself! They pulled out and he did it and it was a hit. It just happened! We just were living music and creativity and it just happened,” recalls Colter. “There was nothing planned. Do what you can, the way you see it, and hope for the best. That was his aim.”

When it’s offered that Honky Tonk Heroes, the rugged 1973 album composed almost entirely of songs by a then-unknown Billy Joe Shaver, is rather hard to imagine with a horn section, Stewart groans and Colter merely rolls her eyes.

“I love the stuff he did with Chet Atkins as much as I love the stuff he did on his own. I think he was great no matter who was producing him,” says Dierks Bentley, who grew up in Arizona. “He really did stir it up and kick down a lot of doors. For the rest of us, a lot of things are taken for granted, like having a say on who plays on our records and writing our songs and how they sound. A lot of that is an ode to Waylon and his lawyer at the time, who really changed the way things were done in Nashville. I think he has a real mystique and coolness about him that you can’t manufacture.”

By the mid-1970s, Jennings’ unmistakable stamp was all over country radio. A solo version of “Good Hearted Woman” reached No. 3 in 1972 and the beloved duet version with Nelson won a CMA award three years later. He also wrote his first No. 1 single, “This Time,” as well as future hits like “Are You Sure Hank Done It This Way,” “I’ve Always Been Crazy” and “Rainy Day Woman.” The brashly-titled 1976 collection, Wanted: The Outlaws, with selections by Jennings, Nelson, Colter and Tompall Glaser became country music’s first million-selling album, even though many of the tracks had been previously issued.

Throughout the 1970s, Jennings supplemented his original material with songs by Ed and Patsy Bruce (“Mammas Don’t Let Your Babies Grow Up To Be Cowboys”), Bobby Emmons and Chips Moman (“Luckenbach, Texas”), Bob McDill (“Amanda”), Shel Silverstein (“The Taker”) and even Neil Young (“Are You Ready For The Country”). His first No. 1 hit of the 1980s was “I Ain’t Living Long Like This,” written by Rodney Crowell. Jennings promptly returned to the top of the country chart as a songwriter with the iconic “Theme From The Dukes of Hazzard (Good Ol’ Boys)” and served as the TV series’ wise narrator. He reunited with Nelson on the No. 1 hit, “Just to Satisfy You,” which they co-wrote, then brought Cash and Kristofferson to the party for the enduring Grammy-winning single, “Highwaymen,” written by Jimmy Webb.

Although he can’t pinpoint one specific song as his father’s signature hit, Shooter points to “Don’t You Think This Outlaw Bit’s Done Got Out of Hand” and “I’ve Always Been Crazy” as quintessential Waylon. But when it comes to his father’s overall catalog, Shooter says, “All those songs are totally timeless. They’ll always stand up because they came from a real place. They weren’t crafted songs. They were written from the heart.”

“Waylon, on his records, represented the good, the bad, the dark, the light, everything about country music,” Bentley believes. “The temptations and trials, but also breaking through and doing your own thing and finding success on your own terms. He really was a ground-breaker for a lot of other artists, as far as forcing his will to be able to write his own songs, use his own studio, use his own band and have more of an involvement in the music being put out there.”

Although Jennings continued to write and release singles, his career momentum faded after moving to MCA Records in the mid 1980s. (His final No. 1 hit, “Rose In Paradise,” peaked in 1987 and he went missing from the Top 10 after 1990.) However, he did earn his GED during this time, finishing an education he abandoned in the tenth grade, and conquered a cocaine addiction. His candid autobiography, Waylon, was released in 1996. When Jennings died in 2002, Shooter Jennings performed “I’ve Always Been Crazy” at the funeral. Meanwhile, Kristofferson delivered “I Do Believe,” a song that he reprised for the new trilogy of albums.

“I want people to hear ‘I Do Believe,’” Stewart insists. “Sure, you know ‘Good Hearted Woman’ but ‘You Asked Me To’ and ‘Belle of the Ball’ and these other songs are so profound. Waylon left such a mark on this business, so I hope by engaging these young people who loved him that a whole new generation will discover him. There’s so much to discover about him. It’s a whole lot more than The Dukes of Hazzard.”

At that last comment, Colter starts applauding.

“I’m just delighted that a new generation will come to know Waylon’s songs,” she concludes. “I’ve found the younger people, especially the young rockers, are so able to get into the history, maybe more than other people who were a part of it. They’re going to really search and they’re going to know him. That thrills me and puts a smile on my face.”