Kris & Waylon

Kris & Waylon / Kris Kristofferson & Waylon Jennings

Waylon Jennings was lost to the world 15 years ago this month. 

Kris often talks about that rear view mirror that we all have to look into at some point, & ever more often as we get older. A man’s friends and foes often reveal a lot about them as a person. Waylon Jennings is a superstar in his own right.

Let’s take a look at what we know about his friendship with Kris Kristofferson.


Kris & Waylon 

Kris & Waylon – Life & Times

Waylon Arnold Jennings was born a Texan on 15 June 1937. Buddy Holly hired him to play bass, arranged his first recording session & it was Waylon who gave up his seat (for Richardson/the Big Bopper) on that ‘plane that crashed in 1959 – ending the lives of Holly, Richardson & Valens along with Peterson, the pilot.


  • Waylon & Kris both found their own way to Nashville.
  • Both men found themselves in conflict with the recording industry (Waylon with A&M over recording style)
  • Both had trouble getting their music played on country radio stations
  • Waylon & Kris both appeared in movies. (Waylon in Nashville Rebel in ’66), & in TV shows (Waylon in 2 episodes of the Dukes of Hazzard)
  • Both men appeared in Outlaw Justice (’98), along with Willie Nelson

Waylon shared a flat with Johnny Cash who would later become Kris’ mentor.

  • Waylon recorded Kris & Silverstein’s song The Taker in ’71

Jennings was part of the Outlaw Country movement of the ’70s. He recorded with Willie Nelson (& others) in ’76 on the album, Wanted! The Outlaws. This album was the first in country music to go Platinum. 

  • Like Kris (& many other musicians of the time), Waylon battled with addiction. Cocaine & amphetamines were Waylon’s monkeys. Kris used to drink heavily
  • Both were inducted into the Country Music Hall of Fame, Waylon in 2001, Kris in 2004.


Waylon formed the Highwaymen along with Kris Kristofferson & Willie Nelson after the 3 of them answered the call by Johnny Cash to appear in his Christmas Special in ’84. This inspired the supergroup that is now part of country music history.


Kristofferson reportedly told the Los Angeles Times (speaking of Waylon Jennings) that Waylon Jennings was an American archetype, the bad guy with the big heart. 

Waylon said of Kris, “When I first met Kris Kristofferson he was really shy – In a loud sort of way”. You can hear this on the clip below where they sing Sunday Morning Coming Down together (1985 TV – The Door is Always Open)



Credits:  HallofFame, Waylon KrisonWaylon ,

The Clip  is a 3.31 minute piece used here for educational purposes only. If you would like to watch the show please contact the owner. No copyright infringement is intended. Texas image is Public Domain here

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