John Prine Meets Kris Kristofferson: How One Night In Chicago Changed Country Music Forever

John Prine and Kris Krisotfferson
Don Paulsen/Michael Ochs Archives/Getty Images

You just have to love when someone pays it forward.

Kris Kristofferson is truly one of the most unique humans in country music history.

Before playing music full time, Kris racked up a resume that can stand toe to toe with pretty much anyone’s, especially when you consider he did all these things before he was 30 years old: Published writer, Golden Gloves boxer, three sport college letterman, Rhodes Scholar, Army Ranger, and helicopter pilot. (And those are just the “prestigious” accomplishments)

Despite all the success he had in his life, when he made the decision to fully chase the music dream, his family was extremely unhappy and actually disowned him, which you can read all about in this piece.

Kristofferson moved to Nashville in 1965 with little more than a wife and sickly young son, medical debt, a motorcycle, and a dream. To pay the bills, he began taking odd jobs, including as a janitor at Columbia Records.

He specifically applied for the custodial role at Columbia Records after a chance meeting with June Carter. He’d given her some demo tapes and asked her to take them to her husband, Johnny Cash, and while she did give Johnny the tapes, they wound up in a pile with all the other demos he had been pitched.

While working at Columbia Records, he would inevitably run into the country stars of the day, but folks like Cash, George Jones, and Bob Dylan didn’t normally take songs from the guy sweeping floor, and Kris, at this time, was no exception.

That’s when Kris decided he needed something big to get their attention and settled on landing a helicopter on Johnny Cash’s front yard to personally deliver his demo tapes, one of which being the now iconic “Sunday Morning Coming Down”.

Although neither Johnny nor June was there that fateful day, word got around and Johnny took a listen to those tapes and realized this janitor was way more talented with a pen than a broom.

From that point, Kris’ career was pretty much a rocket ship and he quickly became one of the most recognizable figures in country music history, but the fame and fortune that came his way never made him forget what it took for him to break into the industry, and a few years later, he did the same for an artist that would go on to inspire countless numbers of aspiring songwriters.

According to a Facebook post from his own account shortly after his death, John Prine was cutting his teeth in the Chicago folk music scene and was truthfully not getting anywhere despite a tenacity that would provide the groundwork for why so many artists looked up to him.

In 1971, Kristofferson was playing a 4-night residency at the Quiet Night, a small venue on the northside of the Windy City, and acclaimed songwriter Steve Goodman was in his ear the whole time saying he had to go listen to some local act.

Well, Sunday night rolled around and Kris finally agreed to go, so after his show they headed across town to John Prine’s gig at the legendary Earl Of Old Town, a popular folk music spot. Fun fact, the Earl Of Old Town closed a long time ago and the space now houses Corcoran’s, an Irish pub where many episodes of our very own Whiskey Riff Raff podcast were planned. There’s a newspaper clipping of Prine framed on the wall.

But back to John Prine… by the time they got there it was around 2am and the place was closing up. Prine’s set was over and he was just waiting for his paycheck so he could leave, but Kris asked him to get back up on stage and play a few songs for him to hear.

When Kris Kristofferson asks to hear a few songs, you play a few songs, and John hopped up and played 7 more songs while the waitresses counted tips. Apparently Kris liked what he heard, so he bought John a beer and asked him to play those 7 songs again along with anything he had written, and Prine happily obliged.

Everyone departed and I’m sure John was holding onto hope that something would come of it, and sure enough a few nights later Kris invited him to open his show at the Bitter End in New York City. Little to John’s knowledge, there was an executive for Atlantic Records named Jerry Wexler in attendance and he liked what he heard so much that he called John up at 10am the next morning and offered him a record deal.

Prine later talked about what happened next:

“I told my dad when I got the record contract. He was sitting on the front porch watching the cars go by and drinking his beer. And I told him they gave me $25,000 and a record contract. And he was real silent and then he looked over at me and he said, “Watch out for those F’in lawyers.” I thought that was good advice”

It was advice that he would end up taking about 10 years later after he got fed up with the commercialized corporate music industry and opened his own label, Oh Boy Records, in Nashville in 1981.

But between signing that first deal and making his own label, Prine had a good amount of success. His self-titled debut album is one of the most critically acclaimed of all time, featuring staples like “Angel From Montgomery”, “Illegal Smile”, “Sam Stone”, and “Paradise”, and he would release his first ever Billboard Top 100 Album with Common Sense in 1975.

As we know, Prine’s music would go on to inspire an insanely long list of artists, including Sturgill Simpson, Jason Isbell, Tyler Childers, and Kacey Musgraves, but it’s possible that none of them, or any of us, would have heard his music if it wasn’t for Kris Kristofferson making a 2am trip through Chicago to listen to a then no-named artist play.

What would country music be like today if there was no John Prine? Would have the resurgence of “real” country music? Would unsigned artists have the confidence to do it their way, buck the system, and build a fanbase organically to the point where they’re pretty much a mainstream act without a dime of corporate money? (Cough, cough, Muscadine Bloodline).

Who would “your favorite artist’s favorite artist” be? What if his example and way with words never had the chance to spread and inspire the great music we all love today?

Artists lifting other artists up instead of fight to “keep their spot” is good for everyone. The rise of independent music is a great example of this continuing to be played out today, but it’s important we recognize the legends that started that trend in the face of no shortage of reasons not too.

Johnny Cash helped give us Kris Kristofferson, who helped give us John Prine, who helped give us Sturgill Simpson, who helped give us Tyler Childers, who helped give us, well I think I’ll stop here because the lineage is going to spread quite wide with Tyler Childers, who I personally think was more instrumental in the resurgence of quality songwriting and true country instrumentation throughout the genre than anyone else in the past decade or so.

If there’s a lesson somewhere in here for us common folks, maybe it’s to be a bit more helpful. Whether at work, with our family and friends, or with strangers, you never know what that person will go on to do if you personally give them a little nudge.

Let’s have a Friday and listen to two artists whose influence on country music can never be overstated: Kris Kristofferson and John Prine.

A beer bottle on a dock



A beer bottle on a dock