Nothing Left to Lose

Some stories in music history are interesting because they are true. And they are told over and over again as part of the mythology. There’s a story about Kris Kristofferson flying a helicopter onto the property of Johnny Cash so he could get some songs to him. What makes the story so entertaining, while providing insight into Kristofferson’s persona, is that it is true. Not only can Kristofferson fly helicopters, but he was also a captain in the army. And there’s more to Kristofferson’s early days. He attended Oxford University on a Rhodes Scholarship. Declining a post as a professor of English literature at West Point, he did what every former army captain and Rhodes Scholar would do—he took a job as a janitor. Kristofferson worked his custodial duties at Columbia Records’ Nashville studio in the mid-60s. While he was emptying ashtrays and sweeping the floor, Bob Dylan was recording Blonde On Blonde. The budding songwriter had the chance to sneak a peek at some of the sessions, but either because he was too shy or feared being fired, he never met Dylan.

For all his achievements, it’s the songs that Kristofferson wrote that have made him one of the most important and legendary musical artists of the past 40-plus years.

What Kristofferson loves more than anything else (even writing songs) is spending time with his wife Lisa and any number of their five children at his home in Hawaii. On a sun-drenched day in spring, Kristofferson, home only a few days after wrapping up a movie, spoke in that deep, craggy voice that was even softer and rougher than usual around noon. He quickly brightened up and became excited, though, when talking about the songwriting process, saying with a laugh, “I write them a lot slower than I used to.” When pressed further about how he writes, Kristofferson said, “I still carry the same things around in my head. I just carry them around longer… The song will probably be about some emotional change that has gone on in my life or something I’m feeling strongly about at that time. I doubt that after I’ve been doing it for so long anything can really change.” He paused and then, prideful and almost apologetically said, “I just do the best I can every time.”

The best he can has been songs and albums that have endured over the years. “Help Me Make It Through the Night” and “Me and Bobby McGee” are two examples of songs Kristofferson wrote that resulted in big hits for other artists. Some of the other classic songs Kristofferson wrote include “Sunday Morning Coming Down,” “Lovin’ Her Was Easier (Than Anything I’ll Ever Do Again),” and “For The Good Times.”

As the 60s turned into the 70s, Kristofferson could have easily continued to write songs that would change country music and become huge hits. Instead, in 1970, his recording career was launched with his signing to Monument Records. Initially, although the album, entitled Kristofferson, was filled with songs that became big hits for country artists, the album’s folksy tone and occasional rock edge didn’t catch on with the country crowd. After Janis Joplin had her huge hit with “Me and Bobby McGee,” the album was re-released and retitled with the name of that famous song in 1971.

Kristofferson began a musical and personal partnership with Rita Coolidge. After divorcing his first wife, Frances, in 1969 after nine years of marriage and two children, Kristofferson married Coolidge in 1973. They recorded three albums together: Full Moon, Natural Act and Breakaway. (The couple divorced in 1980 and have one child.)

Around the time that Kristofferson married Rita Coolidge, his film career really started to take off. In 1973, he appeared in Sam Peckinpah’s Pat Garrett and Billy the Kid. The film also starred Jason Robards, James Coburn and Bob Dylan. Kristofferson said “it was great” working with Dylan, but added, “I felt sorry for Bob because I talked him into it, but Sam was in really rough shape during that time. I’m sure it was an uneasy first film experience for Bob, because Sam was doing some pretty crazy things at the time.”

Bob Dylan obviously doesn’t cover other people’s music often. Dylan did however, cover a Kristofferson song. On the 1986 album Knocked Out Loaded there is a cover of Kristofferson’s “They Killed Him.” Dylan’s version of the song is easily one of the best interpretations of a contemporary song Dylan has ever done. When I told Kristofferson how much I liked the song and asked him about Dylan covering it, Kristofferson, even all these years later, is still thrilled that Dylan even covered him at all, let alone a song of his that isn’t necessarily one of his most popular. “That’s the ultimate trophy—for him to do a song of mine,” Kristofferson stated. I remarked, “He doesn’t cover very many people’s songs.” Quickly responding, Kristofferson said, “No, and the fact that he did that one, which pissed some people off at the time, I thought it was really great.” Kristofferson paused here and became moved again by Dylan’s generous gesture and how much Kristofferson himself loved the song and said, “I’m going to [put] that back in the set. It’s hard to get all the songs you want to do in. I’m glad you said that because I like it, too.”

It’s hard to imagine that anyone who has written as many songs, released as many albums, won multiple Grammy awards and toured as much as Kris Kristofferson has, could also have a film career that includes nearly 100 roles. It’s the directors Kristofferson has worked with that he is most proud of in regard to his film career. “It’s something that I get more amazed about the older I get, that I had the opportunity to work with these guys because I wasn’t a trained actor,” he reflected. “It all happened at the same time. I started performing and I started getting films. I really feel pleased looking at it from this end of the road, that I got to work with so many good people.”

Kristofferson’s film career has been filled with varied roles in many films that have become classics. One film though, that really stands out for Kristofferson is A Star Is Born, for which he won the Golden Globe as best actor. Kristofferson said it is “one of my favorite films.” He talked about what it was like working with Barbra Streisand. “We were battling over a lot of artistic choices at the time, but we came to both be working in the same direction and it was really sweet.” In discussing the film further, Kristofferson explained why none of his songs were used in the film. “It was pretty difficult because I could not use my own material…because of some publishing deal they had where Barbra’s company had to own them all or something,” he began. “But, Barbra really liked my band so much so that she used them more than I did, but it made it so much more real to me to have those guys working with me making the best music we could.”

In reflecting on how being a musician and an actor has worked for him, Kristofferson said, “The acting and performing onstage probably helped each other.”

Kristofferson talked about working in the Highwaymen with Willie Nelson, Johnny Cash and Waylon Jennings. “Every one of those guys was one of my heroes before I ever knew them,” began Kristofferson about the three albums and touring he did as part of the Highwaymen. “They got to be close friends,” he stated. “I had to pinch myself every night when I’d be up there looking to my right and there’s Johnny Cash and the next guy’s Waylon and the next guy’s Willie, and we went all over the world together and it’s still kind of sinking in on me.”

Our conversation kept returning to writing. Relaxed and in a reflective mood, Kristofferson confided, “Time’s running out and I would like to write some kind of autobiography, and if I get in the habit, I might even start writing fiction again.” Given what he had just said and the fact that he has worked in film and done so much writing, I wondered if he’d ever considered writing a screenplay, to which he said, “I thought about it and could still do that, too.”