At 78, what Kristofferson is feeling is age, if his albums This Old Road and Feeling Mortal are anything to go by. Both acknowledge the much shorter future than the long past.
"Yeah, each of my albums is a summing up of what I was going through at the time. I'll probably continue to do that, although I don't write as fast as I used to."
But because of that accumulated experience and his instinctive, honestly hewn style he can record even faster. Most of This Old Road in 2006 - the year after he was last in New Zealand - took less than two hours, recorded by producer Don Was in the place Kristofferson felt most comfortable: his bedroom at home in Hawaii.
If that sounds a bit slippers 'n' pipe, the old troubadour still pulls out assertive songs of dissent. He rumbles with throaty laughter at the suggestion You Don't Tell Me What To Do on last year's Feeling Mortal probably speaks more to 14-year-olds than his septuagenarian peers.
"Yeah, that's been a constant in my life. I don't always agree with everybody else and songs have always been the natural way of expressing myself. The song are reactions to things although I've not been in trouble for that for a long time.
"Ever since I was moved by the killing of the Kennedys I was aware of what we were supposed to stand for as Americans."
The Kennedys become a touchstone in the conversation - "Since they killed the Kennedys I haven't seen that many visionary people in leadership" - and although an Obama supporter "since he was congressman" he remains troubled by the state of his nation. But if politicians failed to articulate vision he'll agree that sometimes - from Bob Dylan to Steve Earle and his fellow travellers - the role has fallen to musicians.
"There've been musicians who've done that. Willie Nelson was always an inspiration to me and still is.
"The great thing about my life is the people who were my heroes turned out to be my closest friends, like the guys in the Highwaymen," he says, mentioning the 80s/90s country supergroup of Johnny Cash, Waylon Jennings, Willie Nelson and himself.
"I still think Johnny Cash should be on Mt Rushmore."
Well if him, then all of you, Kris?
"Well, I used to feel like that when I was on stage with them. One end you've got Willie and the other you've got Waylon and Johnny. That was truly something."
Parallel to his music career Kristofferson - from Pat Garrett and Billy the Kid (by Sam Pekinpah and with Bob Dylan and Jason Robards), A Star is Born (with Barbra Streisand), into Blade (with Wesley Snipes) and to this year's adaptation of Willy Vlautin's noir-novel The Motel Life, Kristofferson has enjoyed a significant movie presence. But he says he's never had a leading-role script since Freedom Road, a television mini-series in 1979 with Muhammad Ali set in the days after the American Civil War.
"I think maybe it was political things I was saying then, and I didn't agree with the powers that be in Hollywood. I believe the Secretary of State, I can't remember his name but a Republican, went to the studio heads and said they should avoid such expressions of the unattractive history of the country."
If Kristofferson remains outspoken, he has always been respected because he's always been honest, even about his vocal and guitar-playing shortcomings.
"It would be hard to escape that," he laughs, "but I'm just grateful that given those shortcomings, I can go around the world doing it.
"You know, I've got very few regrets and most days I'm feeling grateful for the life I've lived. I've got eight beautiful kids and I've been married for over three decades to the woman I love.
"I feel very lucky."
Who: Legendary singer-songwriter Kris Kristofferson
Where: The Civic, Auckland, Wednesday April 30; Michael Fowler Centre, Wellington, May 5; Regent on Broadway, Palmerston North, May 6; Napier Municipal Theatre, May 7
Key albums: Feeling Mortal (2013); Please Don't Tell Me How The Story Ends (2010); Jesus Was a Capricorn (72); The Silver Tongued Devil and I (71); Kris Kristofferson (1970)
- TimeOut