Top 10 Kris Kristofferson Songs (2023)

Kris Kristofferson has led one of the most interesting lives of any songwriter in country music, and it shows in the richly textured and subtly nuanced songs that he writes.

The iconic songwriter started life as the son of a military officer, and he moved around the country before ending up in California, where he graduated high school. Kristofferson was a gifted student and athlete, and he earned a Rhodes scholarship to Oxford University, where he took part in rugby and boxing before earning a Master's degree in English Literature. He also served as a helicopter pilot in the Army and refused a position teaching at West Point to drop out and pursue songwriting full-time.

Kristofferson's varied life experiences and literary bent both helped shape him into one of the most unique songwriting voices of his generation, whose songs have been covered by artists as diverse as Johnny Cash, Waylon Jennings, Ray Price, Ronnie Milsap and even Janis Joplin, in addition to his own solo hits. Though Kristofferson has had a long and successful solo career, many of the Top 10 Kris Kristofferson Songs are familiar primarily because of iconic recordings from other artists.

  • 10

    "They Killed Him"

    From: 'Repossessed' (1986)

    Kristofferson turned more and more to themes of politics and social justice for his later work, including many of the songs on Repossessed. Though it didn't have the chart success of some of the other top Kris Kristofferson songs, "They Killed Him" still stands as one of his best. The lyrics pay tribute to his heroes, including Martin Luther King, Jr., Mohatma Gandhi and Jesus Christ. Kristofferson builds the narrative masterfully, explaining how each of those men came in peace, and ending each story with the powerful refrain, "My God, they killed him." Johnny Cash and Bob Dylan also cut their own versions of the song.

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  • 9

    "Loving Her Was Easier (Than Anything I'll Ever Do Again)"

    From: 'The Silver Tongued Devil and I' (1971)

    Kristofferson scored one of his biggest solo hits with "Loving Her Was Easier (Than Anything I'll Ever Do Again)," which was released as a single from his sophomore solo album. Interestingly, the song was never promoted to country radio; instead, it became a hit in the Adult Contemporary format. Roger Miller also cut the song.

  • 8

    "For the Good Times"

    From: 'Kristofferson' (1970)

    "For the Good Times" appeared on Kristofferson's landmark debut album, which helped re-write the rules of Nashville songwriting. It had been previously recorded by Bill Nash, but by far the most recognizable version of the song came from Ray Price, who took it to the top of the charts in 1970. His recording of "For the Good Times" took Song of the Year honors at the ACM Awards. Perry Como also had a hit with "For the Good Times" in the UK in 1973.

  • 7

    "The Taker"

    From: 'The Silver Tongued Devil and I' (1971)

    Kristofferson collaborated with Shel Silverstein -- who would go on to find fame as the author of children's books -- on "The Taker," which appeared on his second album in a horn-laden rendition that has a Tex-Mex flair. That same year, Waylon Jennings cut a better-known version and made it the title song of his album The Taker/Tulsa, which featured a total of four Kristofferson cuts. His take on the song reached No. 5.

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  • 6

    "Please Don't Tell Me How the Story Ends"

    From: 'Natural Act' (1978)

    Kristofferson and his then-wife, Rita Coolidge, recorded a duet version of "Please Don't Tell Me How the Story Ends" in 1978, the year before they divorced. But it was Ronnie Milsap's recording that brought it to the public's attention. Milsap first recorded the song for his debut album in 1971, then re-recorded it for his Pure Love album in 1974. That version reached No. 1 on the country charts. Willie Nelson, Bobby Bare, Joan Osborne and even Sammy Davis, Jr. are among the other artists who have recorded the song.

  • 5

    "The Pilgrim, Chapter 33"

    From: 'The Silver Tongued Devil and I' (1971)

    Kristofferson's second album is a treasure trove of masterful songwriting, and one of the standout cuts is "The Pilgrim, Chapter 33." The songwas inspired by an encounter with Johnny Cash and ultimately written as an homage to all of the gifted, difficult artists who had served as an inspiration to Kristofferson, including Dennis Hopper, Bobby Neuwirth and Ramblin' Jack Elliott. The song contains one of Kristofferson's most iconic lyrics: "He's a walkin' contradiction, partly truth and partly fiction /Takin' every wrong direction on his lonely way back home."

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  • 4

    "Why Me"

    From: 'Jesus Was a Capricorn' (1972)

    Kristofferson is known for the gritty realism of many of his best songs, but "Why Me" is a stark contrast, a country-gospel song written from the heart and without the poetic bent and hard-nosed world viewof some of his other efforts. Kristofferson was inspired to write the song at a low point in his life after attending a church service where Larry Gatlin sang a song called "Help Me Lord," and Gatlin sings backing vocals on the track, which is a direct plea for divine intervention: "Lord help me, Jesus / I've wasted it so help me Jesus / I know what I am /Now that I know that I've needed you / So help me Jesus, my soul's in your hands." The song was Kristofferson's only solo country hit, reaching No. 1 in 1973.

  • 3

    "Help Me Make It Through the Night"

    From: 'Kristofferson' (1970)

    Kristofferson was inspired to write "Help Me Make It Through the Night" after reading an interview Frank Sinatra gave to Esquire magazine. He cut it for his debut album, but it's also one of the most-recorded songs in his songbook, with cuts from Loretta Lynn, Lynn Anderson, Tammy Wynette, Dottie West, Ray Price, Johnny Cash, Charley Pride and many more. Sammi Smith scored the biggest hit on the song; her 1971 rendition reached No. 1 on the country charts and won a Grammy for Best Female Country Vocal Performance.

  • 2

    "Me and Bobby McGee"

    From: 'Kristofferson' (1970)

    "Me and Bobby McGee" became one of the most iconic songs of the 1970s. Kristofferson co-wrote it with his producer, Fred Foster, whose friend Boudleaux Bryant had a secretary named Bobby McKee. In Kristofferson's original, Bobby is a woman. Roger Miller first cut the song in 1969, and Kristofferson included it in his 1970 debut album, but it was Janis Joplin's 1971 recording that launched the song, helping cement Kristofferson's position as one of the most important songwriters of his generation.

    (Video) Kris Kristofferson - Sunday morning coming down (1970)
  • 1

    "Sunday Mornin' Comin' Down"

    From: 'Kristofferson' (1970)

    Among the many iconic songs on Kristofferson's self-titled debut album, "Sunday Mornin' Comin' Down" is arguably the most important for its long-term impact. First cut by Ray Stevens in 1969, the song was then cut by Kristofferson himself in 1970, but the best-known cover came from Johnny Cash that same year. He took the song to No. 1 in 1970, winning the CMA Award for Song of the Year in the process. The song helped launch Kristofferson on a career trajectory that saw him become one of the most prolific and important songwriters of the 20th century.

What Are Your Favorite Kris Kristofferson Songs?

With decades and decades of songs to draw from, this list of the Top 10 Kris Kristofferson Songs doesn't come anywhere near to doing justice to his overall output as a songwriter and artist. Did we leave out one of your personal favorites? Or include a song that shouldn't be here? Let us know in the comments section below.

Next: Top 10 Merle Haggard Songs

(Video) K.r.i.s K.r.i.s.t.o.f.f.e.r.s.o.n 2023 MIX ~ Top 10 Best Songs ~ Greatest Hits ~ Full Album


Top 10 Kris Kristofferson Songs? ›

Kristofferson briefly dated Janis Joplin before her death in October 1970. His second marriage was to singer Rita Coolidge in 1973, ending in divorce by 1980. Kristofferson married Lisa Meyers in 1983.

What was Kris Kristofferson's greatest hits? ›

16 Biggest Hits: Kris Kristofferson
  • Me and Bobby McGee. Me and Bobby McGee. ...
  • Jody and the Kid. Jody and the Kid. ...
  • Sunday Mornin' Comin' Down. Sunday Mornin' Comin' Down. ...
  • From the Bottle to the Bottom. From the Bottle to the Bottom. ...
  • Once More with Feeling. ...
  • For the Good Times. ...
  • The Taker. ...
  • Help Me Make It Through the Night.

Were Kris Kristofferson and Janis Joplin lovers? ›

Kristofferson briefly dated Janis Joplin before her death in October 1970. His second marriage was to singer Rita Coolidge in 1973, ending in divorce by 1980. Kristofferson married Lisa Meyers in 1983.

Did Kris Kristofferson ever have a hit song? ›

Kris Kristofferson – “Sunday Mornin' Comin' Down”

55 on the Country Singles chart in 1969, but it was “The Man In Black” who made it a worldwide hit.

What hit songs did Kris Kristofferson have? ›

The Best Kris Kristofferson Songs
  • New West | 2009. Good Morning John. ...
  • Mercury Nashville | 1986. They Killed Him. ...
  • Monument | 1970. To Beat The Devil. ...
  • Monument | 1991. From The Bottle To The Bottom. ...
  • Sony | 1972. Jesus Was A Capricorn (Owed To John Prine) ...
  • Sony | 1972. Nobody Wins. ...
  • Sony | 1971. Loving Her Was Easier. ...
  • New West | 2009.
Jun 23, 2022

Who wrote the most hit songs in history? ›

Most number one singles by a songwriter (US/UK)

The most successful songwriters in terms of number one singles are John Lennon (1940-80) and Paul McCartney (b. 18 Jun 1942).

What did Kris Kristofferson think of Barbra Streisand? ›

Kris Kristofferson said: "Filming with Barbra Streisand is an experience which may have cured me of the movies." Kris Kristofferson did not get along with the director.

Are Willie Nelson and Kris Kristofferson friends? ›

Willie Nelson and Kris Kristofferson are great friends.

Are Barbra Streisand and Kris Kristofferson friends? ›

Streisand called Kristofferson "one of my favorite leading men" before inviting the music legend to the stage. It's clear the co-stars have remained close in the decades since sharing the screen. As for their personal lives, Streisand has been married to actor James Brolin since 1998.

What was the song Kris Kristofferson wrote about Janis Joplin? ›

Me and Bobby McGee,” though usually associated with Janis Joplin (who recorded it shortly before her death in 1970), was written by Kristofferson and first recorded by Roger Miller in 1969.

What rank did Kris Kristofferson achieve in the military? ›

Kris was a Golden Gloves boxer and went to Pomona College in California. From there, he earned a Rhodes scholarship to study literature at Oxford University. He ultimately joined the United States Army and achieved the rank of captain. He became a helicopter pilot, which served him well later.

Was Kris Kristofferson a good boxer? ›

In his younger years, Kristofferson was an accomplished athlete, skilled at rugby and American football. He also was a Golden Gloves amateur boxer. Pretty much anything that required giving or taking a beating, he was up to it.

Who sang with Kris Kristofferson at Joni Mitchell? ›

Joni can be seen clapping her hands over her head at the end of Chaka's dynamic performance. Kris Kristofferson, the oldest of the headliners at the the age of 82 is joined on stage by Brandi Carlile who probably comes in as the youngest member of the group.

Did Kris Kristofferson serve in Vietnam? ›

In 1965 I volunteered for Vietnam–and was turned down. They told me I was going to be assigned to West Point to teach English. I decided to get out and go to Nashville instead….”

Are Kris Kristofferson and Rita Coolidge still friends? ›

When they divorced she did not ask him for anything. However, in 2016 Coolidge told People that she and Kristofferson still shared a bond. Coolidge married Tatsuya Suda, a world leader in computer architecture research, on June 19, 2004, in the Cook Islands.

How many wives has Kris Kristofferson had? ›

Kris Kristofferson was married to Frances Beer for 9 years, Rita Coolidge for 7 years, and Lisa Meyers for 40 years.

What was Kris Kristofferson's number one song? ›

1: “Why Me” Kris Kristofferson has one single No. 1 hit as a solo artist and that is “Why Me.” He recorded the track with backing vocals from his wife Rita Coolidge and Larry Gatlin. The song was inspired by Gatlin's track, “Help Me Lord,” along with his church.

Who had a huge hit in 1976? ›

The Top 100, as revealed in the year-end edition of Billboard dated December 25, 1976, is based on Hot 100 charts from the issue dates of November 8, 1975 through October 30, 1976.
Billboard Year-End Hot 100 singles of 1976.
1"Silly Love Songs"Wings
2"Don't Go Breaking My Heart"Elton John & Kiki Dee
3"Disco Lady"Johnnie Taylor
97 more rows

What song did Kris Kristofferson write for Janis Joplin? ›

Me and Bobby McGee,” though usually associated with Janis Joplin (who recorded it shortly before her death in 1970), was written by Kristofferson and first recorded by Roger Miller in 1969.


1. Cher - Country Medley (with Kris Kristofferson & Rita Coolidge) (The Cher Show, 04/13/1975)
2. The Highwaymen - Silver Stallion
(The Highwaymen)
3. Bobby Bare - Come Sundown She'll Be Gone
(Country Road TV)
4. Kris Kristofferson - Love Is The Way
(Kris Kristofferson)
5. Casey's last ride by Kris Kristofferson play along with scrolling guitar chords and lyrics
(Joanne Cooper Play Along Videos)
6. You Ask Me To (Waylon Jennings Cover)
(Carson McKee)
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