100 Greatest Men: #11. Waylon Jennings

Waylon Jennings100 Greatest Men: The Complete List

Waylon Jennings was the very embodiment of the country music outlaw movement in the seventies, demonstrating that legendary music can be made if artists are liberated to create it in the way that they want to.

Jennings was born in Littlefield, Texas, and was playing the guitar and singing on the radio by the time he was twelve years old.    Jennings dropped out of school at age fourteen, and picked cotton while pursuing music in his spare time. When he moved to Lubbock, he became friendly with rising rock star Buddy Holly, who took Jennings under his wing. Holly produced a single for Jennings and had him fill in as a bass player in the Crickets.

Tragedy struck when Cricket died in a plane crash.  By a twist of fate, Jennings had given up his seat on that plane to the Big Bopper, an act of generosity that saved his life.   Jennings formed his own rockabilly band called the Waylors, which led to an independent label deal in 1961.  When their releases were unsuccessful, Jennings moved to Los Angeles, where he had another unsatisfying label experience with A&M Records, which wanted him to move away from country and toward a pop sound.

Jennings then moved to Nashville, where Chet Atkins brought him on board the RCA label.   He had only moderate success for a long stretch of time.  Feeling that label interference was the problem, he renegotiated his contract to allow for more artistic freedom.  Soon, Jennings was recording albums of songs written by writers like Billy Joe Shaver and Kris Kristofferson, and incorporating the driving honky tonk sound that would become his trademark.

As fans responded positively to the new material, Jennings became more aggressive with his sound and image.  His live shows became legendary, and a concert recording in 1976 became one of his biggest-selling records.  He collaborated with Willie Nelson on several occasions, topping the country charts and winning major industry awards for their work together.   As the seventies drew to a close, his album sales were reaching groundbreaking heights for a country artist, with several albums selling millions of copies each.

He struggled with addiction in the eighties, but his career recovered from it, and he was still scoring hits until the end of that decade.  While he was one of many acts that faded from radio during the nineties boom, his concert popularity never faltered, nor did his artistic approach to his work.  His work during the nineties was critically acclaimed, much like that of Nelson, his Outlaw contemporary.

Health struggles kept him from recording toward the end of his life, and while industry honors were not important to him, his son Buddy proudly represented him when he was inducted into the Country Music Hall of Fame in 2001.   Only a year later, Jennings succumbed to his illnesses, passing away at the age of 64.

Essential Singles:

  • Only Daddy That’ll Walk the Line, 1968
  • This Time, 1974
  • I’m a Ramblin’ Man, 1974
  • Are You Sure Hank Done it This Way, 1975
  • Good Hearted Woman (with Willie Nelson), 1975
  • Luckenbach, Texas (Back to the Basics of Love), 1977
  • Mammas Don’t Let Your Babies Grow Up to be Cowboys (with Willie Nelson), 1978
  • Don’t You think This Outlaw Bit’s Done Gone Out of Hand, 1978
  • Amanda, 1979
  • America, 1984

Essential Albums:

  • Sings Ol’ Harlan, 1967
  • The Taker/Tulsa, 1971
  • Lonesome, On’ry, and Mean, 1973
  • Honky Tonk Heroes, 1973
  • This Time, 1974
  • Ramblin’ Man, 1975
  • Dreamin’ my Dreams, 1975
  • Waylon Live, 1976
  • Ol’ Waylon, 1977

Next: #10. George Strait

Previous: #12. Eddy Arnold

100 Greatest Men: The Complete List


  1. He’s probably ranked a little too highly. I always felt Waylon’s best songs pre-dated the so-called “Outlaw” era. Moreover, he recorded a lot of garbage after he gained control of his own recordings and didn’t have someone to keep his worst impulses in check. Even now I can’t stand to listen to “Clyde” or “Shine”

    I would nominate 1968’s ONLY THE GREATEST as Waylon’s best album. Track for track it never lets up on the quality

  2. Good write up, but sorry to see no mention of his role in the Dukes of Hazzard, both as narrator and singer of one of the most well-known TV themes in history.

  3. Waylon is not ranked too highly! I’d say he’s ranked about right, depending on who is still to come on the list.

    All the albums listed here as “Essential” are stone cold classics.

  4. I feel that Waylon was always an outlaw, in the sense that he was a tough-minded individual who would not kowtow to rules and regulations, even those on Music Row; and I think this was evidenced early on with “The Only Daddy That’ll Walk The Line” and his version of “Brown-Eyed, Handsome Man.” This is not something that I think most of the poseurs of the so-called “bro country” movement get when they drop his name in their songs.

    Amusingly, I had heard his and Willie’s classic 70s style being something on the order of “Bro country for old men”–minus the misogyny of most bro-country songs, of course.

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