Waylon: Outlaw Hero

My copy of the album, 45 years old
Waylon Jennings’ favorite album, 1975

Waylon Jennings (1937 – 2002) was at his best when he was Lonesome, On’ry, And Mean. Which was a song he recorded in 1974, about the time I first heard him and his band. It was sometime in the early Seventies. I was a bartender at the Warehouse, a night club in Denver, Colorado, where he performed.

Waylon became an instant hero to me. His music, live, spoke to me and my idea of living free. I operated the service bar in the back corner of the show room. The only folks allowed in were the cocktail waitresses and the band members. We had a good time, drinking and snorting cocaine.

Waymore, as he was sometimes called, created a new brand and style of music that took over American Country music, and even crossed over into Rock and Pop. He broke all the rules. He did things his way and that pissed off Nashville, the seat and heartbeat of country music. His music was called Rockabilly at first, combining traditional country swing with rock, blues, and jazz riffs. Eventually, “Outlaw Country” became its own genre.

Some definitions

are needed:

Hero: a person who is admired or idealized for courage, outstanding achievements, or noble qualities. That definition is consistent across all cultures. Waylon Arnold Jennings, without a doubt, satisfies two of those criteria. Noble qualities is debatable. However, one of his mantras was “I never intentionally hurt anyone.” Also up for debate. Self defined as a “fighter”, isn’t a fighter’s intention to hurt their adversary? There are many contradictions in Waylon’s life, which speaks to the Outlaw persona.

Outlaw: not a criminal in this context; but a person who operates outside conventional rules, or boundaries. Again, in Waylon’s words, “You all have a good time. Do what you want.”

One reason Waylon became a hero to many Americans in the Seventies.
Straight from the heart

Of course, some behaviors will be “criminal”. Such as drug use, speeding, trespassing, etc. and so on. Or not wearing a seat belt (or a mask?) And also not being politically correct, following convention. Jennings quotes Bob Dylan regarding this: “To live outside the law you must be honest.” Waylon: “To us, Outlaw meant standing up for your rights, your own way of doing things.” (pg. 223) In other words – being free.

Cowboy: in this context is best defined by his song Don’t Let Your Babies Grow Up To Be CowboysHe and Willie Nelson wrote this song together. The Cowboy hero/myth/legend was a huge part of Americanism in the 20th Century. Paula Cole’s song Where Have All The Cowboys Gone nails it.

This book

is as much a history book as autobiography. If you want to understand the 20th Century in America, this is a must read. Jennings’ memory is extraordinary. I’ll not recount his account here. I’ll only say – it’s accurate. If you want to understand American music and the people who made it – read this book! You’ll get up-close and personal accounts of Hank Williams, Buddy Holly, Elvis Presley, Jonny Cash, Willie Nelson, drug use and so on. And the women who loved them.

Jennings includes an index and a discography. There are maybe a thousand persons mentioned! Not only musicians, but people and organizations who had a great impact on American culture: President Jimmy Carter, Muhammad Ali, Presidents Ronald Reagan and Bill Clinton, the Hell’s Angels, the Oakland Raiders football team and so on.

Waylon Jennings was an influencer before the word existed.

Ladies Love Outlaws

might be the takeaway from this book. As well as an explanation for why things unfold the way they do in the world.  It’s a song Waylon wrote in 1972. I can attest to its veracity.

Me as Waylon
The lady and the outlaw



There are three, at least, evolutionary explanations for this:

  1. Display hypothesis
  2. Show-off hypothesis
  3. Handicap hypothesis

And yet no one wants to talk about this. Because it’s politically incorrect.





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