Most people don’t equate the term “country music outlaw” with the term “woke.” But despite the ignorance of such things, the fact is the group of outlaws also known as “The Highwaymen” that consisted of Kris Kristofferson, Johnny Cash, Willie Nelson, and Waylon Jennings were quite “woke” — especially for their day. 

A prime example of that is from 1992. The scene was a Bob Dylan tribute concert that was as “star studded” as they come. Many of the time’s top artists were there to pay tribute to Dylan by performing songs of his in their own way.

Two of those artists were Kris Kristofferson and Sinead O’Connor — two artists that probably didn’t travel in the same circles or have many fans in common. In fact, after an incident on Saturday Night Live just a few days ago, where O’Connor ripped up a picture of the Pope to protest the church’s refusal to properly address the issue of priests sexually abusing children. Most people who saw the SNL episode or heard about it in the media over the next days didn’t get the nuance of what O’Connor was protesting. All most people saw was her “disrespecting” the Catholic Church and Jesus.

So, it is safe to say, O’Connor was not very popular at that moment.

Kristofferson introduced her at the tribute concert as a person who represented “courage and integrity.” And with that she took the stage to a mix of cheers and boos. But the boos seemed to dominate the response.

O’Connor was seemingly frozen out on the stage as the boos and jeers continued. Kristofferson then went out and whispered in her ear “don’t let the bastards get you down.” Sinead was supposed to sing Dylan’s “I Believe In You.” She called off the band and then stepped to the mic and rattled off the lyrics acapella  to a Bob Marley song called “War.” The same song she sang on SNL. When she completed the lyric, she then headed off stage as the boos increased. Kristofferson met her in the wings of the stage and escorted her off in a comforting and supporting manner.

This is how Kristofferson described the event:

In (an) interview with with Miriam O’Callaghan on Saturday Night with Miriam in August 2010, Kris explained about one of their first meetings: “Sinead had just recently on Saturday Night Live torn up a picture of the Pope, in a gesture that I thought was very misunderstood. And she came out and got booed. They told me to go get her off the stage and I said “I’m not about to do that”

He added: “I went out and I said ‘Don’t let the bastards get you down.’ She said ‘I’m not down’ and she sang. It was very courageous. It just seemed wrong to me, booing that little girl out there. But she’s always had courage.”

Sinead O’Connor always seemed like an artist that would rather be heard than adored. She never shied away from speaking out against injustice no matter where she saw it or how powerful that purveyor of injustice was.

And Kris Kristofferson got that — and supported it. So did the folks in the audience that understood Bob Dylan. Unfortunately, those people were outnumbered even at a tribute to Dylan himself. Dylan would rather be heard than adored. But most didn’t get that, as they were there to adore Dylan rather than actually internalize what Bob Dylan was about.

Years later, Kris Kristofferson would work with Sinead O’Connor. They did a fine duet of the country classic “Help Me Make It Through The Night” which is considered one of his finest compositions. He would also write a song in tribute to her, called “Sister Sinead.” That song would probably shock many country music fans, especially the ones who like to convolute their music tastes with right wing politics. Those same people would probably think people like Kris Kristofferson and his outlaw buddies would agree with them when they express their ideologies through country music. Newsflash — they wouldn’t.

O’Connor made public the fact that her and Kristofferson went on to have a brief fling, and later felt he was “toxic” in their personal relationship, but that really isn’t relevant here. At that moment in 1992, Sinead O’Connor was in a rough spot, and “woke” Kris Kristofferson was the 1st and only person who was willing to offer her understanding and compassion, and not judgement and condemnation when she needed it.

Check out the event in 1992 below …

Their duet of Help Me Make It Through The Night below …