3 of the Most Perfectly Written Outlaw Country Lyrics of the 20th Century

Outlaw country is the kind of subgenre that remains enjoyable and unforgettable, no matter how many years have passed since its heyday in the 20th century. And when it comes to lyrics and songwriting, you just can’t beat the following outlaw country songs. Let’s revisit a few classics, shall we?

Videos by American Songwriter

“Highwayman” by The Highwaymen (1985)

“I fly a starship / Across the Universe divide / And when I reach the other side / I’ll find a place to rest my spirit if I can / Perhaps I may become a highwayman again / Or I may simply be a single drop of rain / But I will remain / And I’ll be back again.”

The Highwaymen was an outlaw country supergroup composed of Willie Nelson, Waylon Jennings, Kris Kristofferson, and Johnny Cash. They complemented one another beautifully and kept the outlaw country torch lit through the 1980s. But when it comes to this legendary song, I still get goosebumps when Cash’s line comes in. His voice was incredibly iconic, and his particular part of “Highwayman” is riveting. Interestingly enough, this song was originally written by Jimmy Webb in the 1970s.

“Mammas Don’t Let Your Babies Grow Up To Be Cowboys” by Waylon Jennings and Willie Nelson (1978)

“Mamas, don’t let your babies grow up to be cowboys / Don’t let ’em pick guitars or drive them old trucks / Let ’em be doctors and lawyers and such.”

There’s no reality in which this list would be complete without mentioning Willie Nelson and Waylon Jennings outside of The Highwaymen. And yet, they make it to this list with a cover song. This humorous tune with a touch of seriousness was originally penned by Patsy and Ed Bruce in the 1970s.

“It’s Morning (And I Still Love You)” by Jessi Colter (1975)

“Have you ever been / At the end of the day / When you held the world / And you let it get away?”

An outlaw country icon who deserves so much more love for her contributions to the genre, Jessi Colter could have made it to this list of beautiful outlaw country song lyrics with several different songs. I went with “It’s Morning (And I Still Love You)”. It’s just so gorgeous, and it also happens to be the first song by Colter I ever heard. And it was a hit for her back in 1976, peaking at No. 11 on the Hot Country Songs chart.

Photo by Karen Wiles/Newsday RM via Getty Images