Top 10 Kris Kristofferson Songs

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.

Sterling Whitaker is a Senior Writer and Senior Editor for Taste of Country. He focuses on celebrity real estate, as well as coverage of Yellowstone and related shows like 1883 and 1923. He’s interviewed cast members including Cole Hauser, Kelly Reilly, Sam Elliott and Harrison Ford, and Whitaker is also known for his in-depth interviews with country legends including Don Henley, Rodney Crowell, Trace Adkins, Ronnie Milsap, Ricky Skaggs and more.


  • 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.

  • 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.

  • 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 song was 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.”

  • 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 view of 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.

  • 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.

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