5 of Kris Kristofferson’s Most Heartwrenching Song Lyrics

The late great Kris Kristofferson penned many heartwrenching and beautiful song lyrics, and picking the most beautiful of those lyrics is no easy feat. Still, these four songs have a special place in our hearts. 

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This short list is far from exhaustive, but we think these four Kristofferson classics are worth revisiting for their lyrical beauty.

1. “Tell Me One More Time”

This underrated track from the 2009 album Closer To The Bone deserves way more love than it gets. It’s a lovely little song about love and not giving up, with some loaded and beautifully written lyrics. “Look for me to go on living / If you’re loving me or leaving darling / Tell me one more time before you do” is just one line that comes to mind.

2. “This Old Road”

A classic from 2006, “This Old Road” is one of Kristofferson’s most relatable songs. He was 69 when he wrote it, and the song is very much an ode to anyone who is struggling with the inevitable process of aging. 

A few noteworthy lyrics include “smiling ain’t so easy now” and “I guess you count your blessings with the problems that you’re dealing with today.” When describing tough times, Kristofferson refers to struggle as “one more rainbow for the road.” 

Gettin’ old is far from easy, but at least we got to be alive at the same time as Kris Kristofferson.

3. “Lovin’ Her Was Easier (Than Anything I’ll Ever Do Again)”

The best song lyrics Kris Kristofferson ever wrote can be found in his 1971 hit “Lovin’ Her Was Easier (Than Anything I’ll Ever Do Again)”. The song was originally penned for Waylon Jennings, who did release his own version, but nothing beats Kristofferson’s version.

It’s a devastating and uplifting song all in one. “I have seen the morning burning golden on the mountain in the skies / Aching with the feeling of the freedom of an eagle when she flies / Turning on the world the way she smiled upon my soul as I lay dying / Healing as the colors in the sunshine and the shadows of her eyes” is just one verse out of three that hits you in the gut.

4. “Feeling Mortal”

Kristofferson likely didn’t intend for this 2013 song to be as heartwrenching as it is in the wake of his passing, but it’s certainly a heartwrenching song for us and all of his fans. It’s another song about aging and declining, but it’s more of Kristofferson’s own meditation on his life. 

“Wide awake and feeling mortal / At this moment in the dream / That old man there in the mirror / And my shaky self-esteem” is just heartbreaking.

Photo by Tim Mosenfelder/Getty Images

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