60 Years Ago: Kris Kristofferson Gets His Start in Music … As a Janitor
It’s not where you start, it’s where you end up. Alan Jackson got his start in the music business as the mail room boy at CMT. John Anderson got his start roofing the Grand Ole Opry House. When Kris Kristofferson arrived in Nashville on November 1st, 1965, he got his foot in the door by taking a job as a janitor at the Columbia Recording Studios sweeping floors and emptying waste baskets. Incidentally, all three men ended up in the Country Music Hall of Fame.
For Kris Kristofferson, taking a job as a janitor was probably the most humbling of all. Alan Jackson and John Anderson came from the working class. Kris Kristofferson had been named a Rhodes Scholar at Oxford University. He’d also been an officer in the US Army, making it to the Captain rank as a trained Army Ranger and helicopter pilot. But his passion to want to become a songwriter is what compelled him to move to Nashville, and take whatever job he could to be closer to the music.
It wasn’t just a pay cut and a demotion in social status that Kris Kristofferson had to endure to chase his dream. His family disowned him for the decision. Kris Kristofferson was supposed to be an academic. He volunteered for Vietnam while in the Army and stationed in West Germany. But noticing Kristofferson’s knack for the written language, the Army assigned him to teach English at West Point. Kris asked for a discharge, and picked up a mop instead.
Things didn’t go especially well for Kristofferson at the start. The words of his landmark song “Sunday Morning Coming Down” were taken from his real life experience. Estranged from his family, failing at making it as a songwriter, he was nearing the end of his rope. However, that training as a helicopter pilot came into use in his songwriting career after all.
While still working as a studio janitor, Kristofferson also took part-time work with the National Guard to help pay the bills. To try and get Johnny Cash’s attention, Kristofferson decided one day to deviate from his flight plan in a helicopter while on a training run and landed in Johnny Cash’s front yard in Hendersonville.
What happened next depends on who you ask, but according to Cash, Kristofferson came sauntering out of the helicopter with a beer in one hand, and his demo tapes in another, demanding to be heard. Kristofferson painted a more subdued picture, saying, “Y’know, John had a very creative imagination. I’ve never flown with a beer in my life. Believe me, you need two hands to fly those things.I still think I was lucky he didn’t shoot me that day!”
Whatever story you believe, the daring mission resulted in Johnny Cash listening to those demos, and getting Kris Kristofferson on the Newport Folk Festival lineup where Cash invited him out on stage. This is when the world was officially introduced to Kris. When Johnny Cash recorded his version of Kristofferson’s “Sunday Morning Coming Down” and it won the CMA Award for Song of the Year in 1970, Kris became one of the hottest songwriters in the business.
Things ended up working out pretty well for ol’ Kristofferson. Along with becoming an award-winning songwriter, he became a successful performer himself, started being cast in movies, became an American heartthrob, dated Barbara Streisand and Janis Joplin—not bad for a former janitor—and he eventually married Rita Coolidge.
Through his songs and their transformational power in country music, Kris Kristofferson wouldn’t just prove his family wrong, he would revolutionize the mindset the entire listening public had about country, and clue them into the poeticism and the power that country music could wield through written word set to rhyme. This would open up the entire genre to an entirely new audience, and a new era as the Outlaws came to prominence in country.
But none of this might’ve happened if Kris Kristofferson wasn’t willing to take a chance on himself, and willing to do whatever it took to make his dream happen, from commandeering a United States helicopter to pay a visit to Johnny Cash, to scrubbing a commode in a recording studio.
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November 1, 2025 @ 9:50 am
That’s a wild story. I think Dottie West was a big help to Kris as well. I recall her saying she used to have all the unknown, struggling songwriters and musicians come to her house and she would make dinner for everyone. I recall in an interview that she said he gave her his “Help Me Make It Through The Night” to record, and she turned it down, thinking it was too sultry for her image. She completely regretted it.
November 1, 2025 @ 2:33 pm
RIP Kris. Thankfully his amazing songs will live forever.
November 1, 2025 @ 4:21 pm
Good friend of the family beyond humble. a all around genuine person loved him So did my mom
November 1, 2025 @ 4:58 pm
Interestingly, the first artist to record a Kristofferson song when Kris came to Nashville was a an artist who’s not all that well-known now, but was a popular middle-of-the-road country singer of the era, and was sometimes called “the Perry Como of Country Music”: Roy Drusky. The song, “Jody and the Kid,” was a modest hit for him Drusky 1968.
Here, 30-some years later, Drusky told the back story and some other historical anecdotes and performed the song on the Country reunion series. Drusky died in 2004.
https://www.youtube.com/watch?v=jzMzVjlj32s&t=3s
https://www.youtube.com/watch?v=0VhktmOy8EI
November 2, 2025 @ 9:19 am
In addition to his talents as a songwriter & singer, Bill Anderson is also a credible country music historian. So I’m rather surprised that both he and Roy Drusky got their facts so wrong on this one. “Jody And The Kid” was not Kris Kristofferson’s first success as a songwriter.
Months after Kris moved to Nashville in 1965, Dave Dudley (who was Drusky’s Mercury label-mate at that time) recorded Kris’ song “Viet Nam Blues.” Derived from his military service and his own experiences, the talking-blues song was an answer to the growing anti-war protests and sentiment during that era. Dudley chose that song for his album of patriotic themed songs recorded in October 1965. That same month Johnny Wright’s “Hello Vietnam” topped the country chart. Given that success, Mercury selected “Viet Nam Blues” for a single release in early 1966 and that recording ultimately rose to #12.
https://www.youtube.com/watch?v=sjz0aYPChEM&list=RDsjz0aYPChEM&start_radio=1
“Jody And The Kid” proved much less successful peaking at #24 for Roy Drusky in September 1968.
A couple of other notes:
– Kristofferson released two of his own songs, “Golden Idol” b/w “Killing Time” as an Epic single in late 1967. That recording did not chart.
– “Sunday Morning Coming Down” was first released as a single by Ray Stevens. His Monument Records version stalled at #55 in late 1969. Johnny Cash’s live version recorded during a broadcast of his ABC-TV show in early 1970 hit #1 later that year.
Here’s Ray’s recording
https://www.youtube.com/watch?v=0uXj7EGyGBA
November 2, 2025 @ 12:24 pm
You can’t rely on entertainers for precise history. Entertainers, first and foremost, tell stories in a way to engage their audience. And this is a forum where artists–many with failing memories–swap tall tales.
Seems Dusky did a very early recroding of a Kristofferson song, Drusky was THERE to perform, so Bill Anderson gave him a clean and engaging intro, calling the first artist to record a Kris song, rather than the more accurate, but unexciting second. And Drusky, as the guest, certainly knew that the last thing a guest is supposed to do on a light-hearted entertainment show is correct the host.
I’ll give them both a pass on this minor bit o misinformation.
November 3, 2025 @ 7:56 am
Entertainers indeed amend and embellish stories to fit their own narrative. But completely ignoring Dave Dudley’s hit recording of Kristofferson’s song is puzzling. Whether intentional or not it’s a slight to Dudley who took a chance by recording a song by a then-unknown writer. Kristofferson’s career received a big boost when he really needed it.
A significant amount of misinformation exists on YouTube and the internet in general. It’s unfortunate whenever those lies are perpetuated and magnified by those that repost them to other sites where the lies are given additional oxygen. Due diligence should be exercised before any reposting video or article. Sadly too many people take posts at face value and do not question their accuracy, truthfulness or integrity.
The lesson here is that it’s better to be part of the solution rather than part of the problem. Had this falsehood not been corrected visitors to this site would have been mislead and Dave Dudley would have been denied his well-earned credit for his role in boosting Kristofferson’s early career.
Good for Drusky that he also took a chance with one of Kris’ early songs. But he was not the first.
November 3, 2025 @ 8:52 am
“But completely ignoring Dave Dudley’s hit recording of Kristofferson’s song is puzzling. Whether intentional or not it’s a slight to Dudley…”
I can say as a member of the media, when things are forgotten or overlooked, it’s rarely if ever meant as a slight, and is very often simply an oversight. No human possesses omniscience, though we’re expected to as members of the media.
November 2, 2025 @ 6:16 pm
Most of this I know is true, he was a Rhodes Scholar, went to teach later at Oxford U. His father was a career military. Wanted Kris to follow him. He did go rogue with a US Army helicopter from Ft Bragg to Johnny Cash’s home in Hendersonville also in NC, not even close. The rest is history. Saw him and then wife Rita Coolidge in 1975 in Charlotte.
November 3, 2025 @ 4:20 am
Nah, the first one(s) who recorded a Kristofferson song, was Jack Sanders with “Vietnam Blues” in 1965, and Dave Dudley got a minor hit with his version in 1966 (also recorded in 1965).
November 3, 2025 @ 10:57 am
I recognize Roy Drusky as a co-writer of “Alone With You,” made a hit by Faron Young back around ’59 or ’60. And covered awful well, in my estimation, by Sierra Ferrell at that Nashville venue with all the tinsel hanging down.
https://www.youtube.com/watch?v=D2vXBciojf0&list=RDD2vXBciojf0&start_radio=1
Faron Young and Lester Vanadore the other co-writers
November 1, 2025 @ 5:32 pm
Him and Billy Joe are the absolute kings in my opinion!!!!
November 1, 2025 @ 8:45 pm
Kristofferson, was a great writer, singer, andaddlituon to country music. Kris, Willie, Waylon saved the real thing. Thanks fellas
November 2, 2025 @ 5:35 pm
The one song I loved by him was why me lord 💞 I never knew he could sing. . to me for years he would sing a song do others would record it . And make a hit with it. I was blown away when he put his heart ❤️ in that song. . I thought after all these years s he does have a voice .just like Willie nelson he made 82 albums before anyone knew who he was. Another great writer. . then he made his best song and did not sing thru his nose. And I loved his best song ever. Kiss big booty good bye. . I always knew if he would just hang in their he would fly naly make a nice recording. .
November 2, 2025 @ 9:23 am
Great story! Now discover me. I am a great lyricist!! BMI writer and publisher
November 2, 2025 @ 9:28 am
Much more than just a country singer/songwriter. His acting was pretty damn good too.
November 2, 2025 @ 9:38 am
Loved him, in A Star Is Born, with Streisand.
November 2, 2025 @ 9:52 am
I woke up this morning, and put on my cleanest, dirty shirt… and the beer I had for breakfast wasn’t bad, so I had one more for dessert…
November 3, 2025 @ 8:15 pm
that line is iconic!
November 2, 2025 @ 12:08 pm
Loving her was easier than anything I will ever do again is absolutely my favorite. Lost my sweet hubby of sixty years and everytime I hear this I think of him and a flood of tears follow.
November 2, 2025 @ 12:55 pm
His folks lived next to my friend’s house ( the Hays family) in Fallbrook, CA (San Diego).and Kris was often there when hed have some down time…Not sure if the Kristopherson house is still in their family line ..prob sold long ago ..Anyway Kris was quite an amazing talent ..and so wonderful he followed his heart where he needed to go. Ironically my friend Bob Hays because a famous Actor ….so he and Kris knew the demands of celebrity..!
November 2, 2025 @ 5:43 pm
Also loved him .in a star was born. . With some actress named Barbara She made a few good movies. . She was a good actress I wonder what happened to her. . Also wille was a better actor then a nose singer. I think if he had his nose fixed he would be successful recording artist.
November 3, 2025 @ 12:27 pm
On TV one time KK said his band told him he sounded like a duck
November 2, 2025 @ 6:01 pm
I love Kris, but…he’s a bit overrated??
A lot of his songs to me are kinda folk/soft rock/pop and very much of their time.
He’s great! But from a country music perspective, is he really one of the best songwriters of the time?
November 2, 2025 @ 8:46 pm
Kris also flew commercial helicopters for PHI as an oil rig transport after he quit the Army. That’s a relatively high-paying job, at least relative to janitorial wages, so I’m pretty sure things would have worked out for him if the whole singer/songwriter/actor gig didn’t pan out
November 3, 2025 @ 5:56 pm
Wow, Kris had only one hit single. Why Me Lord. I had no idea. I thought he had some other major hit singles of his own. He did well on the album charts. I understand his immense songwriting superstardom, and I understand his appeal due to his good looks and being amazingly photogenic. But I’ve never understood the hype and hoopla of Kris as a recording artist thrust into rarified air on the level of, say, Willie Nelson.
His name was always tossed in the air, for decades, when people would name major singers.
On the other hand – I recognize that a body of work can transcend and I think this is what worked for Kris as far as recognition and elevation as a recording act. After all, he is quoted as saying “I can’t sing, I sound like a frog!” His albums have character and lend substance and layer to his legend as a songwriter. He wrote, he recorded, he acted; he was a mainstream celebrity in 70s pop culture making movies with the likes of Burt Reynolds and was in some Oscar nominated movies.
He seemed like a cool guy that you could say hello to on the street.
November 6, 2025 @ 8:16 am
Like other greats (Dolly and Johnny come to mind) Kristofferson had deep character. I will never forget him to standing up for Sinéad O’Connor when she was getting booed at (I think it was) the Bob Dylan 30th Anniversary concert.
November 6, 2025 @ 9:19 am
Another other connection to country legends was the story of “Why Me?” Connie smith took him to Jimmie Rodgers Snow’s church ( Hank Snows son) and during the altar call found himself inexplicably moved to accept Christ as his Lord and Savior…the song came next. Amazing man and life
November 8, 2025 @ 12:13 pm
These “XX years ago” features are my favorite articles on this site, so I hope Trigger keeps writing them, especially ones that focus on great songwriters like Kristofferson.