Kris Kristofferson had a reputation in Nashville.

Brilliant.

Intense.

Hard to read.

EVEN WAYLON JENNINGS WAS SAID TO BE INTIMIDATED BY HIM.

Kris was not the usual country star. He was a Rhodes scholar, an Army helicopter pilot, a boxer, an actor, and a songwriter who could make a country song sound like literature.

But Willie Nelson was not scared.

He heard the music first.

Mammas Don’t Let Your Babies Grow Up to be Cowboys-The American Outlaws

But here’s what made Willie different…

Willie was not trying to outthink Kris.

He was trying to understand him.

A simple country boy with a guitar found common ground with one of Nashville’s most intimidating minds, and that bond helped open the door for the band that will define a whole new genre.

Johnny Cash had no trouble fitting in.

Waylon was a bit hesitant at first.

But once the four men found their rhythm, The Highwaymen became country music history.

And that’s not all…

It is almost ironic that Waylon was nervous around Kris at first, because by the end, they became each other’s chosen family..

Here’s the moment that shows what their bond became…

Here’s the truth…

The Highwaymen were not just four legends sharing a stage.

They were four difficult, brilliant, wounded men learning how to trust each other.

And when Kris reached the end of his life, the story goes that he smiled and told his children he was going to meet his friends.

Waylon and Johnny had already passed away before him.

Now Kris was ready to join them.

So… Which Highwayman do you miss the most?