Waylon Jennings’ Best Quotes of All Time: Lessons of Authenticity from the American Outlaw

by Emily Morgan

There’s a lot to be said for the simplistic yet genuine nature of country music: the artists may come and go, but the lessons of the lyrics remain self-evident. One artist who exemplifies all that is good about country music was Waylon Jennings.

He may have only lived until he was 64, but he packed a life well lived in that small amount of time. 

Waylon Jennings: Philosopher in Another Life

You probably wouldn’t know it from his music, but Jennings dropped out of high school at the age of 16. That minor setback didn’t keep him from pursuing his dreams, nor did it make him any less intelligent than the next guy. In fact, “The Highwayman” often pondered the same ideas and theories studied by philosophers. 

“I mean, I think we’re put here on earth to make your own destiny, to begin with. I don’t think there’s anything you can do this way or that way to change anything.”

Despite his rough exterior as a country music outlaw, Jennings was a fan of the metaphysical. Even though he lacked formal education, Jennings didn’t let that stop him from contemplating life’s most challenging questions. After dropping out of school, Jennings’ perseverance shone through when he worked different jobs, such as stocking shelves in a dry goods store, picking cotton, and driving a truck. What he lacked in academic education, he made up for it with hard work and street smarts. 

Waylon Reminds us to Care about the Music

While the debate continues about the new country music versus the old, outlaw style of country music, Jennings lays it out fairly simply: you have to foster what you create. That’s the beauty of Jennings’ philosophy; it wasn’t complicated or needed to incorporate big vocabulary words. It was evident and easy to comprehend for the average American. 

“You’ve got to care about the music… You’d better not be doing it for the publicity, the fame or the money. And you’d sure better not be doing it because it’s a way to make a living, ’cause that ain’t always going to be easy. You got to believe it, believe in the music. You got to mean it.”

Waylon wasn’t Afraid to be who he was

In the year 2020, it’s commonplace to shy away from offering your opinion in response to the cancel-culture movement. However, Jennings was not a man to hold his tongue when it came to his beliefs. War is never a pleasant conversation topic, but Jennings knew how to use his platform when he saw something unjust occur. 

“The men who could not fight, in a war that didn’t seem right. You let them come home, America.”

Jennings’ “America” was a hit in the summer of 1984. Seamlessly, Jennings captures the spirit of brotherhood that Americans should feel towards one another: “My brothers are all black and white, yellow too, and the red man is right to expect a little from you—promise and then follow through, America” is a reminder that we are all equal, and we have work to do.”

His opinion on draft dodgers is what made Jennings such a well-respected man; he’s not judging them. Instead, he’s praising America for being willing to forgive the men. 

Be yourself, that’s all you’ve got in this World 

If there’s one thing Jennings wasn’t, it was anyone else. The prolific outlaw country singer didn’t care if you loved him or hated him. Instead, he focused on remaining true to himself and his values, even if it didn’t sell records or put him on the Top 40 hit list. 

“Don’t ever try and be like anybody else, and don’t be afraid to take risks.”

Waylon Jennings: More Relevant Now More than Ever

The outlaw movement birthed by county music artists such as Waylon Jennings, Willie Nelson, Kris Kristofferson, Chris Gantry, Johnny Cash, and Merle Haggard wasn’t about selling records, gaining popularity, or selling out shows. Instead, it was unapologetically about the sanctity of individuality— something that seems to be rapidly escaping our modern world. 

No matter who you are, even if you aren’t a fan of his music, it’s impossible not to appreciate the gritty, genuine nature of Jennings’ determination to fearlessly be himself.