100 Greatest Men: #48. Kris Kristofferson

100 Greatest Men: The Complete List

Though his Hall of Fame career has now stretched several decades, Kris Kristofferson will forever be defined by his legendary songwriting in the late sixties and early seventies.

An intellectual of Swedish descent, Kristofferson’s father was in the U.S. military, and as a result, he moved around quite a bit while growing up.   His twin passions were writing and rugby, and he pursued both vigorously while completing his undergraduate studies in California.   He earned a Rhodes Scholarship to Oxford University, and while studying there, he gained distinction in boxing, and more importantly, he began writing songs.

He briefly pursued a performing career while in England, with hopes that success could help him toward his real goal of publishing a novel.   When this was unsuccessful, he succumbed to family pressure and joined the army in 1960.   Five years later, he left the army, which resulted in estrangement from his family, and he arrived in Nashville to pursue his songwriting craft full time.

The cuts came slowly, but after having a few chart hits by artists like Dave Dudley and Roger Miller, he became established around town.   As the sixties turned into the seventies, Kristofferson’s pen became legendary, thanks to a string of hits for other artists.   Sammi Smith’s recording of “Help Me  Make it Through the Night” won him a Grammy for Song of the Year, while he earned the CMA trophy for “Sunday Morning Coming Down” (Johnny Cash) and the ACM trophy for “For the Good Times” (Ray Price.)  Janis Joplin, who Kristofferson had dated for some time, found her greatest success after her death, as her recording of Kristofferson’s “Me and Bobby McGee” topped the pop singles chart for several weeks.

Kristofferson’s notoriety as a writer piqued enough interest in him to lead to a successful singing career of his own.  He had several well-received albums for Monument, two of which sold gold.   Radio was mostly indifferent to the projects, with the glaring exception of his stunning #1 hit, “Why Me”, in 1973.

While he continued to sing and write songs, Kristofferson’s career took a surprising turn toward Hollywood, and he became a legitimate film star, winning a Golden Globe for Best Actor starring opposite Barbra Streisand in A Star is Born.   He also had successful musical collaborations with his wife, Rita Coolidge.   Meanwhile, Nashville stars continued to record his songs, with friend Willie Nelson even recording a platinum-selling tribute album in 1979.

His last major success as a recording artist came in 1985 as part of the supergroup The Highwaymen with Johnny Cash, Waylon Jennings, and Willie Nelson.   That same year, he was inducted into the Songwriters Hall of Fame, while the Country Music Hall of Fame elected him in 2004.

Over the past two decades, he has continued to release albums of self-written material, while continuing to tour and appear in various films, including a prominent role in the Blade trilogy.
Essential Singles:

  • For the Good Times (Ray Price), 1970
  • Sunday Morning Coming Down (Johnny Cash), 1970
  • Me and Bobby McGee (Janis Joplin), 1971
  • Help Me Make it Through the Night (Sammi Smith), 1971
  • Please Don’t Tell Me How the Story Ends (Bobby Bare), 1971
  • Why Me, 1973
  • The Highwayman (with Johnny Cash, Waylon Jennings, and Willie Nelson), 1985

Essential Albums:

  • Kristofferson, 1970
  • Me and Bobby McGee, 1971
  • The Silver Tongued Devil and I, 1971
  • Jesus Was a Capricorn, 1972
  • To the Bone, 1981
  • Broken Freedom Song: Live From San Francisco, 2003

Next: #47. Rodney Crowell

Previous: #49. Toby Keith

100 Greatest Men: The Complete List


  1. It isn’t just Nashville artists and legends that have done his stuff. Gladys Knight had a minor 1972 with “Help Me Make It Through The Night” as well; and Jerry Lee Lewis even made it into the Top 40 on the pop charts with a version of “Me And Bobby McGee” that same year (it was also done by the Grateful Dead). His influence and the respect Kristofferson has had, inside and outside of country music, is enormous.

    And as for films, I would also point out his turn as Billy The Kid (even though he was a decade and a half older than the real-life outlaw) in director Sam Peckinpah’s elegiac 1973 western PAT GARRETT AND BILLY THE KID, opposite James Coburn. That was a very tremendous achievement (IMHO).

  2. I realize we could quibble over some of the rankings all week which is why I won’t do it, but seriously, 48 for Kris is just wrong. “Sunday Morning” and “Help Me Make It Through The Night” alone should earn him a spot in the top ten or at the very least above, say, Charlie Rich or Tim McGraw. Those two songs are true classics.

  3. Virtually every song that anyone remembers from Kris Kristofferson came during one short burst of creativity – everyone cites the same five or six songs and maybe a couple more that were sung by less well know artists (Roy Drusky – “Jody and The Kid”)

    If you rank Kris higher, then what do you do with songwriters who were at least as creative as Kris and far more prolific (over a far longer period of time) such as Harlan Howard, Hank Cochran, Dallas Frazier and Felice & Boudleaux Bryant, songwriters who probably also had more pop success than Kristofferson ?

    If anything I would think you have Kristofferson too high – I’d probably have him in the 60-75 range

  4. Paul,

    your point is well taken and if you see me arguing with some parts of it, know that I do so for purely academic reasons – i.e. sometimes I like to argue :)

    one short burst of creativity – everyone cites the same five or six songs
    You could say the same about Herman Melville – all his memorable work came from the same period (1846 – 1851) and everyone cites that one book. But that still doesn’t change the fact that “Moby Dick” one of the greatest works of literature of all time and as such, it earns its author a high place in the pantheon of writers.

    Also, not that it matters much to me, but there is a world of difference between pop success before Beatles (like e.g. Felice and Boudleaux Bryant had with Everly Brothers) and after.

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