When we think back to the 1950s, often ideas of a squeaky-clean life come to mind. In movies, whenever characters go back in time to the 50s, life always seems so square and simple compared to today. But of course, that wasn’t always the case.

That’s just what we wanted to dive into today. We wanted to look back at three country songs from the 1950s that were anything but square and simple. Instead, they’re dark, insightful, and timeless. Indeed, these are three country songs from the 1950s that are actually perfect for your next karaoke night.

“Don’t Take Your Guns To Town” by Johnny Cash from ‘The Fabulous Johnny Cash’ (1958)

Johnny Cash’s career began in the 1950s thanks to his deep voice, excellent songs, and that chugging guitar behind him. Cash could sing about numbers in the phone book and get a crowd—he was that good, even back then. But one of his maybe lesser-known hits of the day was “Don’t Take Your Guns To Town”, a song with a mighty good lesson for people today.

“Cold, Cold Heart” by Hank Williams (Single, 1950)

There are a number of Hank Williams songs from the 1950s that can shine for Karaoke night, including “Cold, Cold Heart”. The man practically set the foundation for modern country music. Incredibly, though he had a short life (dying at 29 years old on New Year’s Day 1953), he left a lasting legacy of music, including this lamenting track. This one is a real classic for the ages.

“Walkin’ After Midnight” by Patsy Cline from ‘Patsy Cline’ (1957)

Any country and western song that talks about being out late is perfect for karaoke night. You and all your karaoke patrons are, in fact, out late—perhaps even after midnight. So, let Patsy Cline sing about what it’s like to be out late at night, out on the town, in search of something. Hear her vocals belt out “Walkin’ After Midnight” and remember that things weren’t so different in the world, even some 70 years ago.