3 of the Coolest Country Singers in the History of Music

When it comes to music and the people who make it, there is cool and then there is country cool. Sure, it’s easy to come from a big city and put on a leather jacket and wear necklaces or fancy sunglasses. But then there are the people who are the strong, silent type, who can tell how far a coyote is just by hearing it howl and who know how to write a song that cuts to the core of being a human being.

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Indeed, country cool is a real thing, and there have been several country music stars throughout history who have exhibited that sense of cool to the nth degree. That’s what we wanted to examine here today. These are three of the coolest country singers in the history of music.

Johnny Cash

With a voice like Johnny Cash, there is no escaping just how cool the singer was. But add to that his mystique as The Man in Black and his songs about rings of fire and walking the line, and you get one especially cool customer. But wait, we’re not done. Known as one of the quintessential outlaw country stars, Cash worked with everyone from June Carter (his wife!) to Bob Dylan. The cherry on the proverbial sundae, however, is the fact that he recorded a top-notch album from prison, singing about the prison blues or a boy named Sue. What a guy!

Merle Haggard

With 38 No. 1 hits on the Billboard country charts, Merle Haggard was one of the most successful and influential country stars ever. And what a name! Merle Haggard. It just sounds rough. But beyond that, Haggard walked his talk. While Cash sang about being in prison, Haggard spent real time there. But it was his talent with a six-string and a microphone that saved his life. He got out of jail and pursued a career in music, bringing his man’s man sensibilities to the stage. Today, he is remembered as one of the most important figures in the genre.

Kris Kristofferson

Kris Kristofferson had a presence about him. He was gruff but sweet. Thoughtful yet brusque. He pined over the ways of love, and yet he could write a song as easily about drinking and riding the rails as he could about settling down. Not only that, but Kristofferson was a notable actor, bringing his outlaw sensibilities to the silver screen in movies like the Blade series. Playing the character Whistler, Kristofferson was as believable on screen as he is in the recording studio. Why? Because he’s just so darn cool!

Photo via ‘The Johnny Cash Show’