10 of Kris Kristofferson’s Best Songs [Ranked]

On September 28, legendary country music singer and actor Kris Kristofferson passed away at the age of 88.

Kristofferson’s passing is a significant loss to the entertainment world. Over his nearly 40-year career, he released more than 20 studio albums and was a member of the supergroup The Highwaymen alongside Johnny Cash, Waylon Jennings, and Willie Nelson. A gifted songwriter, Kristofferson wrote hits for legends like Waylon Jennings and Janis Joplin. He also saw incredible success as an actor, starring with Barbra Streisand in the 1976 film A Star Is Born and appearing in many other blockbuster movies.

As we take a look back on his incredible career, it’s only fitting to recognize some of the best songs he ever wrote, which have earned their place in music history.

See a ranking of Kris Kristofferson’s 10 best songs below.

10. “Good Morning John”

“Good Morning John” is a track from Kris Kristofferson’s 20th studio album, released in 2009. Kristofferson wrote the song for his close friend Johnny Cash as a gesture of support during Cash’s journey toward sobriety.

9. “Jesus Was a Capricorn”

“Jesus Was a Capricorn” is the title track from Kris Kristofferson’s fourth album, inspired by fellow singer-songwriter John Prine. Released in 1972, the song became a No. 1 hit on the Billboard Country chart and reached No. 21 on the Billboard 200. The album’s cover featured Kristofferson alongside his soon-to-be wife, Rita Coolidge.

8. “To Beat the Devil”

“To Beat the Devil” is a powerful song from Kris Kristofferson’s debut album, released in 1970. The album also includes well-known tracks like “Me and Bobby McGee” and “Sunday Morning Coming Down.” At the start of the song, Kristofferson talks directly to the listeners, explaining how the song came to be, making it even more personal.

“A couple of years back I come across a great and wasted friend of mine in the hallway of a recording studio,” Kristofferson says in the intro. “And while he was reciting some poetry to me that he had written, I saw that he was about a step away from dying, and I couldn’t help but wonder why. And the lines of this song occurred to me.”

7. “The Pilgrim, Chapter 33”

Kristofferson wrote and recorded “The Pilgrim, Chapter 33” for his second studio album, The Silver Tongued Devil and I, released in 1971. In the spoken introduction to the original recording, he shared that the song was inspired by several of his friends, including Johnny Cash, Dennis Hopper, Donnie Fritts, Billy Swan, Bobby Neuwirth, Jerry Jeff Walker, and Ramblin’ Jack Elliott.

6. “Why Me”

“Why Me” was recorded by Kris Kristofferson in 1972, featuring backing vocals from Rita Coolidge, and rising singer-songwriter Larry Gatlin. Released on the album Jesus Was a Capricorn in 1973, it became the biggest hit of Kristofferson’s career.

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

“Loving Her Was Easier (Than Anything I’ll Ever Do Again)” became Kris Kristofferson’s first charting single and remains one of only two top 40 pop hits of his career. Originally written for Waylon Jennings, the song has since been covered by many country legends, including Willie Nelson and The Glaser Brothers.

4. “For the Good Times”

“For the Good Times” was written by Kris Kristofferson and first recorded by Bill Nash in 1968. It later appeared on Kristofferson’s debut album in June 1970. The song gained widespread recognition when Ray Price recorded it, turning it into a #1 hit single later that month. This success not only solidified Kristofferson’s reputation as one of country music’s top songwriters but also marked Price’s first chart-topping country song in 11 years.

3. “Help Me Make It Through the Night”

“Help Me Make It Through the Night” first appeared on Kris Kristofferson’s debut album. However, it is best known for the version by Sammi Smith, which reached No. 1 on the Hot Country Singles chart. The song also won a CMA Award for Single of the Year and a Grammy for Best Country Song, as well as earning Smith a Grammy for Best Female Country Vocal Performance.

2. “Sunday Mornin’ Comin’ Down”

“Sunday Morning Coming Down” is considered Kris Kristofferson’s breakout song, famously recorded by Johnny Cash. Cash’s version was included on his 1970 live album The Johnny Cash Show, which was recorded at the Grand Ole Opry House and linked to his popular TV show. The album spent two weeks at No. 1 on the Top Country Albums chart and won the CMA’s Song of the Year award.

1. “Me and Bobby McGee”

“Me and Bobby McGee” is arguably Kris Kristofferson’s most iconic song. Co-written by Kristofferson and Fred Foster, it was initially recorded by Roger Miller in July 1969 but gained popularity when Janis Joplin released her version in 1970, just before her death. The song topped the U.S. singles chart in 1971 and has since been covered by legendary artists, including Johnny Cash, Dolly Parton, and Loretta Lynn.