A Battle of Outlaws: Waylon Jennings vs Willie Nelson

Posted by: on Mar 21, 2011 | One Comment

In a battle of outlaws, only the orneriest will survive. Willie and Waylon have a long history together in the “Outlaw Country” subgenre, but how does their actual cred hold up when pitted against each other?


Waylon Jennings: 
Waylon’s father played guitar in Texas dancehalls, and encouraged his son to pursue music. He started his first band at the age of 10, and was later kicked out of music class for not learning to read notes. At 21 he was asked to play bass in Buddy Holly’s band.

Willie Nelson: 
Willie wrote his first song at 7 and joined a local band at age 9. He began performing in dancehalls and honky tonks as a way to earn money aside from picking cotton. Though he finished high school, his early success in music would pull him away from college and into our outlaw hearts.


Waylon Jennings: While working as a DJ, Waylon and friend Buddy Holly were influenced by the Mayfield Brothers of West Texas, as well as other early country and bluegrass acts.

Willie Nelson: Influenced by some of country music’s great forefathers, Willie drew inspiration from musicians like Lefty Frizzell, Hank Snow, Ray Price, Hank Williams, Ernest Tubb and Django Reinhardt.


Waylon Jennings: Despite his dangerous reputation, Waylon’s actual criminal record is limited to a 1977 arrest for cocaine possession that was later dropped. This of course doesn’t mean he never engaged in desperado-esque activities, it just means he never got caught.

Willie Nelson: Willie’s outlaw antics are also thin, with only one recent arrest for marijuana possession. Unfortunately, even this doesn’t impress much when everyone knows you’ve been a pothead throughout your entire career in music. Willie still has a few years left to rob a some trains though… just give him some time.


Waylon Jennings: “Bessie was a lovely child from West Tennessee / Leroy was an outlaw hard and mean / One day she saw him starring & it chilled her to the bone / She knew she had to see that look on a child of her own / ‘Cause ladies love outlaws / Like babies love stray dogs / Ladies touch babies like a banker touches gold / Outlaws touch ladies somewhere deep down in their soul.”

Willie Nelson: “Cowboys are special, with their own brand of misery from being alone too long / You could die from the cold in the arms of a nightmare, knowing well that your best days are gone / Picking up hookers instead of my pen, I let the words of my youth fade away / Old worn out saddles and old worn out memories, but no one and no place to stay.”


Waylon Jennings: While Waylon’s most renowned collaborations are with his competitor in this post, he’s worked with many country greats, including Jerry Reed, Johnny Cash and Kris Kristofferson. He also provided his voice to Family Guy shortly before his death.

Willie Nelson: Willie’s collabs are straight out of country music heaven, and include the aforementioned members of the Highwaymen, as well as Bob Dylan, David Crosby, Bonnie Raitt, Merle Haggard, Emmylou Harris and of course, Waylon.

AND THE ORNERIEST IS: Are/were Willie and Waylon true outlaws? A cocaine addiction in and of itself is not particularly “outlawish” until it lands you in jail, in which case you’d better pray the charges aren’t dropped due to the DEA’s incompetencies (sorry, Waylon). Getting arrested for marijuana possession is nothing to shake a crusty, outlaw stick at either, unless you’re Willie Nelson and, like Snoop Dogg, you’ve built a cult of personality around your drug addiction. Regardless of their lack of true bad boy credentials like illegal gambling or bank robberies, Waylon and Willie are still two of orneriest outlaws in country music, which is why I’m calling this one… a draw. These boys work better as an outlaw team anyway.

Waylon Jenning’s “Lonesome, On’ry and Mean”:

Willie Nelson’s “Whiskey River”: