The Best Waylon Jennings Songs of All Time

DISCLAIMER: I love Waylon Jennings. I've read his autobiography 3 times. I love all phases of Waylon. Young Waylon who played bass for Buddy Holly. Slighty older cool-haired Waylon the front man. The long haired outlaw most people envision when they think of Waylon Jennings (the Waylon and Willie and the Boys version). And, of course, old-man Waylon with is "Country My Ass" (CMA) baseball cap.

The day Waylon Jennings died, I was a college student. I remember that my buddy and I paid tribute to Waylon that night by drinking whiskey (kind of how we paid tribute to everything back then) playing Madden on the Playstation (not necessarily in tribute) and listening exclusively to Waylon Jennings music on Napster. Remember Napster? We must have listened to100 Waylon songs that night.

I didn't grow up on Waylon Jennings, like you might have. I was born in 1980, after "Wanted: The Outlaws" had already made its mark. I knew who he was, and I knew the big hits. But Waylon was one of the first artists I fell in love with on my own. Nobody said "Dude, you gotta listen to this." I decided on my own to dive into Waylon's catalog, and I fell in love. 

So, I present to you, the best Waylon Jennings songs of all time (in my humble, but correct opinion). You will likely disagree with me. But ain't that the best thing about opinions?

Drinkin' and Dreamin'

Waymore's Blues

Are You Sure Hank Done it This Way?

The Conversation

Song for the Life

I've Always Been Crazy

Brown Eyed Handsome Man

If You See Me Gettin' Smaller

Slow Rollin' Low

The Wurlitzer Prize (I Don't Wanna Get Over You)