Top 10 Kris Kristofferson Solo Songs

Kris Kristofferson has had an illustrious career behind the pen, behind the mic, and behind a number of collaborations. His musical chops amounted to a number of hits and, eventually, garnered the attention of Hollywood.

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He is well-known as a quarter of the outlaw country supergroup the Highwaymen and as a duet partner with Rita Coolidge, but his solo career is arguably something to admire more. Here are 10 of Kris Kristofferson’s top solo songs.

10. “The Silver Tongued Devil and I”

Kristofferson crafts a story song in “The Silver Tongued Devil and I,” bellowing, I took myself down to the Tally Ho Tavern / To buy me a bottle of beer / And I sat me down by a tender young maiden / Who’s eyes were as dark as her hair / And as I was searching from bottle to bottle / For something un-foolish to say / That silver tongued devil just slipped from the shadows / And smilingly stole her away.

From his sophomore album of the same name, “The Silver Tongued Devil and I” gallops along with bright strings and matter-of-fact vocals, weaving a tale about the devil reflected back in the mirror.

9. “Help Me Make It Through the Night”

The brightly twinkling ballad, “Help Me Make It Through the Night,” was not only a success for Kristofferson, but it has also been a hit for several other artists.

Since its 1970 release, the country standard has been covered by so many, including Tammy Wynette, Loretta Lynn, Glen Campbell, Joan Baez, Jerry Lee Lewis, Elvis Presley, Mariah Carey, Willie Nelson, Olivia Newton-John, and more.

8. “The Taker”

Another tune from The Silver Tongued Devil and I, “The Taker,” is about a ne’er-do-well lover, and is punctuated by bright Spanish horns, a warm, shuffling beat, and Coolidge’s refreshing backing vocals.

While penned by Kristofferson, “The Taker” was first recorded by country icon Waylon Jennings for his 1971 album of the same name.

7. “From the Bottle to the Bottom”

That’s the way that I’ve been feeling since the day I started falling / From the bottle to the bottom stool by stool / Learning hard to live with losin’ you, Kristofferson howls. The bare bones “From the Bottle to the Bottom” is a tune about a down-and-outer living with heartbreak.

When the song was released as a duet with his then-wife Coolidge, it took home the 1974 Grammy Award for Best Country Performance by a Duo or Group with Vocal.

6. “The Pilgrim, Chapter 33”

From his hit-riddled The Silver Tongued Devil and I, Kristofferson’s “The Pilgrim, Chapter 33” is a song that wafts with mystique.

He’s a poet, he’s a picker / He’s a prophet, he’s a pusher / He’s a pilgrim and a preacher, and a problem when he’s stoned / He’s a walkin’ contradiction, partly truth and partly fiction / Takin’ ev’ry wrong direction on his lonely way back home, the artist lists off, never really revealing the pilgrim’s identity.

5. “Casey’s Last Ride”

“Casey’s Last Ride” is a boot-stomping, spur-spinning cowboy anthem featured on Kristofferson’s 1970 self-titled debut. Full of ominous thunder and then tender strings, the song tells the tale of a lonesome outsider lost in love.

4. “Gettin’ By, High and Strange”

I’ll keep livin’ till the day I die / As long as I can get it up for one more try / Gettin’ by (gettin’ by) high (good and high) / And strange (gonna get some strange), Kristofferson cheekily sings in “Gettin’ By, High and Strange.”

From his 1972 release, Border Lord, the song, like many others on the album, harbors themes of traveling and life on the road, something that became a constant with his building success.

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

The wistful lullaby, “Loving Her Was Easier (Than Anything I’ll Ever Do Again),” is another track from The Silver Tongued Devil and I. It is also another of Kristofferson’s songs that quickly became a highly covered standard among the country music world and beyond.

2. “Sunday Morning Coming Down”

On the Sunday morning sidewalks / Wishing, Lord, that I was stoned / Cause there’s something in a Sunday / That makes a body feel alone / And there’s nothin’ short of dyin’ / Half as lonesome as the sound / On the sleepin’ city sidewalks / Sunday mornin’ comin’ down, moans the melancholy tune “Sunday Morning Coming Down.”

Appearing on his debut album, the Kristofferson penned “Sunday Morning Coming Down” may have been a No. 1 hit for Johnny Cash, but it’s a classic of the songwriter’s all the same.

1. “Me and Bobby McGee”

Kristofferson’s masterpiece just so happens to appear on his already impressive debut. While it was another of his tunes made famous by another artist, “Me and Bobby McGee” is without a doubt the Kristofferson essential. Covered by innumerable acts, it has gone on to span genres, decades, and generations, making it an enduring hit to this day.

Photo by Don Paulsen/Michael Ochs Archives/Getty Images

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