Top Definition
The greatest Country music singer of all time and a legend of the "Outlaw Country" movement when Country was still about the passion of the music. Waylon was originally a bass player for Buddy Holly. After Buddy's death, Waylon began to follow his own act and became one of the founding members of the "Outlaw Movement" of Country -- also known as the greatest music ever created (examples would be Willie Nelson, Johnny Paycheck, Kris Kristofferson, Johnny Cash, Merle Haggard, David Allen Coe, and George Jones). Waylon peaked in the 70's before Country music began to slowly turn to commercialized crap (a process completed by the mid-late 90's). He was married to the very beautiful Jessi Colter, who as the "First Woman of Outlaw Music" would have had no issue in kicking someone like Taylor Swift's scrawny little ass, before passing away in 2002.

Waylon had a very distinctive voice and passion in his music that is un-characteristic of bubblegum Country of today where men wear $4,000 cowboy hats from New York Department stores and women have fake breasts and fake blonde hair. Great Country legends like Waylon Jennings smoked non-filtered Pall Mall's and drank Pabst Blue Ribbon, often drunk as hell before getting up on stage, and still managed to give all their heart in their music. Waylon was a gentleman at heart and like many others in the "Outlaw Country" movement, his body faded away from us all long before the spirit within him could be given proper voice within his music.
"Man, Country just ain't what it used to be!"

"I hear that, we need some Waylon Jennings, Willie, and the boys!"
by JDFP February 14, 2010

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