Kris Kristofferson is one of the most celebrated songwriters and storytellers in American music history. He has written countless songs that have touched people around the world, some more famous than others.
From his earliest days as a struggling songwriter to his later success as an actor and director, Kris Kristofferson’s life reads like a country song with all its twists and turns.
His songs have been covered by artists like Johnny Cash, Willie Nelson, Emmylou Harris, Roy Orbison, Ricky Skaggs, and Jerry Jeff Walker. He has sold more than thirty million albums worldwide.
With so many great songs to choose from it’s hard to pick just 10 that are the best but here they are:
Top Songs by Kris Kristofferson
For The Good Times
This song is one of the most covered country songs. It was originally recorded by Ray Price, but when it hit number one on the charts for him Kris quickly made a version that would become his signature song.
“For The Good Times,” tells about all those things in life we are powerless to stop changing and passing us by with an emotional longing in his voice that makes you feel every word he sings even though he never has had or will have any idea who you are or what your story is.
This song is one of the best because it is so honest and human that it makes you feel not just the story of loss but your own.
Me and Bobby McGee
This is the song that helped Kris Kristofferson become a household name. It was written by his friend Janis Joplin. It tells the story of two people who have nothing in common except they are free together, and “Bobby says don’t ever look back”.
It’s about letting go of everything that would hold you back from being free.
It was number one for four weeks on the Billboard Hot 100 in 1971 and has been covered by artists like Johnny Cash, LeAnn Rimes, Emmylou Harris, Pink Floyd, and Bette Midler.
It is one of the best songs by Kris Kristofferson because it has universal themes that anyone can relate to no matter what their background.
Sunday Mornin’ Comin’ Down
The song talks about a man who is desperately unhappy with his life and wants to end it all.
He recalls a few memories from his childhood that he thinks may have led him down the wrong path but in the end, decides there is no hope for happiness, “There’s nothin’ here worth stealin’, so I guess I’ll go”.
It was recorded by Johnny Cash for his album “The Junkie and the Juicehead Minus Me”. The song tells a powerful story that anyone can relate to and that is why it falls under this category.
Help Me Make It Through The Night
This song was first recorded by Tammy Wynette, but Kris’ version put him on the map. It tells the story of a man who has just been released from jail and goes to see his lady.
He asks her if she will go away with him, but he knows that if she says no it would be better for both of them so they can move on because there is nothing left for either one except pain.
The song was written by Kris Kristofferson. It’s one of the best because it is so honest about how we can hurt each other without even knowing it and that sometimes ending something before it’s gone is better than trying to hold on just for love.
The Pilgrim Chapter 33
This song has a lot of religious imagery which was unusual for Kris, but it tells the story of a man who is on his way to California.
He has left everything behind including his woman and he knows that he will end up alone like all the other pilgrims before him with nothing to show for their journey except scars from life’s battles.
This song was written by Terry Smith. It is one of the best because it is a metaphor for life and how we all end up at the same destination no matter what road we take.
The Silver Tongued Devil and I
Kris wrote this song about his third wife. It tells the story of a man who has been burned by love and knows he can’t trust it anymore.
When temptation comes knocking at his door and seduces him with promises of bliss, he gives in knowing that it is not real because she doesn’t even know what the silver-tongued devil means.
The song falls under this category because it shows how love is often more about what people want rather than who they are.
“Why Me” is about a man who has spent his whole life trying to do the right thing but always ends up alone. He thinks that maybe he is being punished for something.
It was first recorded by Johnny Cash and later covered by artists like Bob Dylan, Waylon Jennings, and Elvis Presley.
The song falls here because it is an honest look at how we sometimes feel like there must be a reason why things happen and that we are being punished for something unknown even though in the end we know it is not true.
New Mister Me
The song is about a man who is in a bad relationship and wants to get out of it but he doesn’t have the courage. He talks about being depressed all day long when you’re living with someone that isn’t right for you.
It is one of the best because it is honest about how hard ending a relationship can be because there are often consequences that go along with saying goodbye. It is a true reflection of what people face in relationships.
A Moment Forever
“A Moment Forever” is about a man who sees an old woman in his rearview mirror and can’t get her off his mind.
He realizes that she has been there the whole time even though they have never met because he knows what it’s like to feel alone all the time.
This is one of the songs by Kris Kristofferson that people love because it is about the idea that we often don’t realize how much someone means to us until they are gone and then suddenly it’s too late.
This song was written by Kris and Will Jennings. It is about a man who has been through so much in his life that he feels like the only thing left to do now is die, but then someone comes along and somehow makes him feel alive again.
The song falls under this category because it talks about how relationships can change us when we are at the lowest point in our lives and makes us feel like we can do anything.
These are some of the best songs by Kris Kristofferson. However, it does not mean that they are the only good ones. There are many other songs that people can listen to for entertainment or inspiration so they don’t miss out on all that Kris has to offer.