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Kris Kristofferson: The Last Outlaw Poet

His all-American journey has taken him from the Army Rangers to Nashville to Hollywood — with a few stops in the gutter along the way

Kris Kristofferson

Kris Kristofferson's all-American journey has taken him from the Army Rangers to Nashville to Hollywood - with a few stops in the gutter along the way.

David LaChapelle

STANDING BACKSTAGE AT THE BEACON Theatre in New York, leaning against a crumbling brick wall in the dark, I could barely see Kris Kristofferson standing to my left. Willie Nelson was in the shadows to my right. Ray Charles was standing beside Willie, idly shifting his weight back and forth. A bit farther along the wall were Elvis Costello, Wyclef Jean, Norah Jones, Shelby Lynne, Paul Simon and respective managers, friends and family. Everybody was nervous and tight. We were there for Willie Nelson’s 70th birthday concert in 2003.

Up from the basement came one of country music’s brightest stars (who shall remain nameless). At that moment in time, the Star had a monster radio hit about bombing America’s enemies back into the Stone Age.

“Happy birthday,” the Star said to Willie, breezing by us. As he passed Kristofferson in one long, confident stride, out of the corner of his mouth came “None of that lefty shit out there tonight, Kris.”

“What the luck did you just say to me?” Kris growled, stepping forward.

“Oh, no,” groaned Willie under his breath. “Don’t get Kris all riled up.”

“You heard me,” the Star said, walking away in the darkness.

“Don’t turn your back to me, boy,” Kristofferson shouted, not giving a shit that basically the entire music industry seemed to be flanking him.

The Star turned around: “I don’t want any problems, Kris – I just want you to tone it down.”

“You ever worn your country’s uniform?” Kris asked rhetorically.

“What?”

“Don’t ‘What?’ me, boy! You heard the question. You just don’t like the answer.” He paused just long enough to get a full chest of air. “I asked, ‘Have you ever served your country?’ The answer is, no, you have not. Have you ever killed another man? Huh? Have you ever taken another man’s life and then cashed the check your country gave you for doing it? No, you have not. So shut the fuck up!” I could feel his body pulsing with anger next to me. “You don’t know what the hell you are talking about!”

“Whatever,” the young Star muttered.

Ray Charles stood motionless. Willie Nelson looked at me and shrugged mischievously like a kid in the back of the classroom.

Kristofferson took a deep inhale and leaned against the wall, still vibrating with adrenaline. He looked over at Willie as if to say, “Don’t say a word.” Then his eyes found me.

“You know what Waylon Jennings said about guys like him?” he whispered.

I shook my head.

“They’re doin’ to country music what pantyhose did to finger-fuckin’.”

Am I young enough to believe in revolution? Am I strong enough to get down on my knees and pray? Am I high enough on the chain of evolution To respect myself and my brother and my sister And perfect myself in my own peculiar way?

—”Pilgrim’s Progress”

KRIS KRISTOFFERSON IS CUT FROM A thicker, more intricate cloth than most celebrities today: Imagine if Brad Pitt had also written a Number One single for someone like Amy Winehouse, was considered among the finest songwriters of his generation, had been a Rhodes scholar, a U.S. Army Airborne Ranger, a boxer, a professional helicopter pilot — and was as politically outspoken as Sean Penn. That’s what a motherfuckin’ badass Kris Kristofferson was in 1979. And now if you go online and watch the video for his 2006 song “In the News,” it’s obvious he is still very much that man.

The son of an Air Force general, Kris walked to grade school barefoot in Brownsville, Texas. He graduated Phi Beta Kappa from Pomona College, studied William Blake and Shakespeare at Oxford, became a U.S. Army captain, was assigned to teach literature at West Point and then abruptly dropped out of the Army to become a songwriter.

Forty years later, Kristofferson is a “unique figure in the history of American music and cinema. The late Sixties and the Seventies saw a creative explosion for American artists. Cinema and rock & roll were in a full-blown renaissance, and Kristofferson stood dead center in both revolutions. He wrote a Number One hit single for Janis Joplin, played at Jimi Hendrix’s last concert, appeared on The Johnny Cash Show with other “new discoveries” like Neil Young, Joni Mitchell and James Taylor, won three Grammy Awards, starred in films directed by the likes of Martin Scorsese, Paul Mazursky and Sam Peekinpah, and became one of the hottest male actors in the U.S. after appearing in A Star Is Born.

Then he played the lead in one of the largest commercial failures in film history, Heaven’s Gate. Kris took the bullet and was shunned from the mainstream, disappearing back into the counterculture.

Today, Kris’ songs have been recorded by more than 500 artists, and he has acted in more than 70 films. In 2006, at the age of 69, he released what is perhaps his finest album, This Old Road. I had been at Willie Nelson’s 70th birthday concert to introduce Kristofferson, whom I had directed in the movie Chelsea Walls in 1999. After both of those experiences, I was enthralled by this man who had lived through so much success and so much failure, both personal and professional, and who had survived with his dignity intact, if not actually heightened. This Old Road motivated me to pitch Kris the idea of my making a documentary about him.

“With all that’s happening in the world today, why would you want to make a film about me?” he asked over the phone. “Let me take you around to a few places I know, and we’ll find some real subject matter.”

I told him that I was aware the world was full of suffering but that I had just seen an old documentary about Woody Guthrie and I was damn glad someone made it.

“Yeah, I’d like to see that,” he said, grudgingly. “It’s just that whole hero-worship thing that bugs me. The cult of personality, you know?”

I explained that I was born in Austin, Texas, in 1970, to a 20-year-old father who did, and still does, a killer cover of “Me and Bobby McGee.” My dad plays the song slower than Janis Joplin did. He pores over the lyrics, enjoying each rhyme, his voice heavy with that song’s melancholy sense of loss. “Freedom’s just another word for nothing left to lose,” my dad will repeat, and then often add, “That may be the best song ever written.” One Sunday morning, we skipped church to go see an early showing of the film Pat Garrett and Billy the Kid. For me, Kris has always been a part of the landscape of my country an amalgamation of John Wayne and Walt Whitman.

As an artist who has tried more than one genre from time to time, I told Kris I felt I had a lot to learn from him, and that I didn’t want to let the opportunity slip away. Eventually we agreed on a compromise: an in-depth interview about his life and work.

I've just got to wonder what my
daddy would've done
If he'd seen the way they turned his
dream around
I've got to go by what he told me
Try to tell the truth and
stand your ground
Don't let the bastards get you down.
—”Don’t Let the Bastards Get You Down”

IT’S AN AWKWARD THING TO INVITE your hero to your house. Early in September 2008, Kris, 72, is seated on my red couch in his black jeans, gray T-shirt and a pair of ancient cowboy boots. As a music fan, I had dreamed of the encounter, but the unforeseen interloper is my own need to express myself, asking questions quickly and then just as rapidly answering them. Periodically, I let him speak.

“What does it feel like to survive a lifetime in the arts with your integrity intact? Why does masculine energy so often manifest itself as idiocy? Why is male sensitivity so often linked with perceived weakness?” I continue, “How do I talk about my beliefs about the war to my brother who just returned home from his second tour in Iraq and one in Afghanistan, when in truth I admire him so much and am actually envious of the courage of his convictions? How do you enjoy your life and at the same time stay responsible to all those who don’t have enough to eat? Who are your heroes?” For a moment, I wait for an answer, then decide to plow forward. “I mean, what happened to the great Southern-progressive Democrat? My grandfather helped kick the Ku Klux Klan out of West Texas.” I tell him this as if he’s interviewing me. “What did LBJ mean when he signed the Civil Rights Act saying, ‘I just lost the South for the Democratic Party for the next 50 years?’ Where are the voices like his? How does one be, as Johnny Cash said; ‘a dove with claws?'”

Kris just kind of laughs. I expect him to say, “I agreed to be interviewed, not to be your goddamn guru!” But he doesn’t. He takes a long beat, then says, “Yeah, that used to piss Shel Silverstein off.”

“What did?” I ask.

“That whole ‘dove with claws’ thing. He just thought, ‘What the hell is that?'” Kris smiles: He has an easy way about him, slow to speak and gentle in his movements.

“Why do you think Cash said it?”

“I think he was feeling the very thing that you’re talking about – that if people think you are against the war, that in some way you’re a pussy.”

“Your first recorded song was a pro-Vietnam War song, right?”

“Yeah, I wrote it when I was in the Army on my way to Nashville, and I came upon a protest march. I had a lot of friends over there; and I was thinking we were fighting for freedom. And I wasn’t thinking very deeply.”

“Why did you end up changing you r mind about that war?”

“I was flying helicopters in the Gulf of Mexico on one of those offshore oil rigs, and I Was talking to some guys coming home. The stories they were telling me were so horrible that I think it just shocked me enough to change my thinking 180 degrees. I’m talking about things like this young vet telling me about taking people up in a helicopter and interrogating them and if they didn’t say what they were supposed to, they’d throw them out, stomping on the fingers of the prisoner holding on to the skids, you know? The guy telling me this particular story was still just a green kid when he returned from the war. The notion that you could make a young person do something so inhuman to another soldier – or even worse, a civilian – convinced me that we were in the wrong. I hadn’t been thinking in human terms of what that military action was.” He pauses, stroking my dog. “I agree with you totally about all the conditioning that makes us want to feel masculine and tough. I mean, I’m sure that’s why I went to Ranger School and Jump School. And I’m proud of that Ranger tab – still am. But the notion of bombing a defenseless country that’s never threatened us and the fact we all accepted it and said, That’s politics!’ Damn. I’m not really interested in polities. We’ve come to a place that I never dreamed and I know my father never dreamed that America would get to.

“That’s why Shel didn’t like that ‘dove with claws’ thing,” Kris goes on.

“He should have just said he was a dove and proud of it?”

“Exactly. ‘Cause people would have accepted anything from John,” says Kris. “We knew he was a man. I don’t really think anybody would have called Johnny Cash a pussy. But John was conditioned, just like you and me. You really have to get past all of that — where you have enough feeling about what’s right and wrong in the world to not give a shit about what kind of names anybody throws at you.

“Also, I had the benefit of an education,” Kris adds. “After college I got to go to Oxford. Given that, I should’ve been a lot smarter than I was, but even still I volunteered for Vietnam. Christ, I should have known better, so I can’t really be critical of individuals. Ultimately, I was really lucky I didn’t go over there.”

I dig Bobby Dylan
and I dig Johnny Cash
and I think Waylon Jennings
is a table-thumping smash
And hearing Joni Mitchell
feels as good as smoking grass
And if you don't like
Hank Williams, honey
You can kiss my ass.
—”If You Don’t Like Hank Williams”

IN THE EARLY 1960s, A MILITARY career was the expected route for the son of an Air Force general, and when I ask Kris about his father, his brother, his sister and his mom, all Kris says is “My dad was a two-star general, and we were a military family,” as if that is supposed to explain everything. After Oxford, Kris flew an Army helicopter in Germany for three years and then volunteered for Vietnam. The Army decided he was too precious to send to the front and instead assigned him to teach at West Point, where they planned to groom him for higher offices. This was not what Captain Kris wanted he wanted to go to the war with his men. Then, while he was on leave in Nashville, his life took a radical turn. He suddenly opted out of the Army and moved his young wife and daughter to Tennessee’s music capital in the hopes of becoming a songwriter. But on the day his former unit was due to depart, he drove from Nashville to Fort Campbell to see his men off; severely intoxicated, he crashed his car outside the base and demanded to be shipped off to Vietnam. His old company commander had to talk the drunk ex-captain out of boarding the plane. He went back to Nashville and started working various construction jobs before accepting a position at Columbia Studios as a janitor. It was 1965.

“I came down to Nashville,” Kris said. “I’d been playing in an Army band, so people introduced me around like I was somebody. Everybody still called me ‘Captain.’ And I wrote seven, maybe 11 songs that first week. I thought if I didn’t make it as a songwriter I would at least get material to be the Great American Novelist. The people and places I was seeing were more exciting than anything I’d ever come across.”

He was introduced to Johnny Cash backstage at the Grand Ole Opry. Kristofferson described Cash as “skinny as a snake, wearing all black and as electrically wired up as anyone I’d ever seen. He was the most driven, gifted, exhilarating and self-destructive artist I’d ever met, and I wanted to be exactly like him. I was going to have to hustle to go out like Hank Williams, ’cause I was already 29. But I thought it was the function of an artist to burn, not rust.”

Four long years went by. There was no novel, no record deal. Very few people noticed him at all. Kris said, “Luckily, I was not a good enough performer to work as a singer at the Holiday Inn… though believe me, I would have jumped at it, ’cause nobody wanted my songs.”

Still, Kris saw Nashville as a “calling of sorts” that felt “right” from the start. “Nashville was like Paris in the Twenties,” he said. “We’d stay up all night trying to knock each other out with our songs. It was both kind of exciting and kind of depressing.”

Kris was bumming around, living the pauper-artist’s life, sweeping up at Columbia and tending bar at the Tally Ho Tavern. Then for two years he spent every other week in the Gulf of Mexico flying helicopters to offshore oil rigs.

“For years I couldn’t get anything cut! And I could have been looked at as a joke here’s this Oxford-educated Army captain come to Nashville, and now he’s emptying ashtrays and sweeping the floors. But I never felt like I was failing….” He pauses. “I guess occasionally I did. When my peers or my parents would remind me.”

Kris’ parents came to Nashville to try to talk some sense into their son, and they ended up disowning him. Looking at footage of Kris back then, chain-smoking, hair obscuring his eyes, clothes filthy, it is easy to understand why a two-star general may have thought his son had lost his mind.

“I told my dad I wanted to be a ‘writer,’ not a ‘songwriter.’ I knew he pictured writers wearing elbow patches and smoking pipes – not smoking the ‘funny stuff’ in Nashville. At home they always said, ‘Now, Kraig’ — he’s my younger brother — ‘Kraig will make money because he cares, and Kris won’t make any ’cause he just doesn’t.’ Well, they were right. I never did care. Still don’t.”

In one of his first interviews, you can see a sweaty, smoky Kristofferson tell a cameraman, “Hey, man, I don’t judge people by how they look and I don’t want to be judged that way. So I just try to look as bad as possible. Makes it easier!” Then he bursts into laughter.

His parents were not amused. His mother told him, in the letter that officially broke ties with her son, that his dreams were adolescent and Johnny Cash was a bad influence: “Nobody over the age of 14 listens to that kind of music, and if they did, they wouldn’t be somebody we would want to know.”

On a Sunday morning sidewalk
Wishing, Lord, that I was stoned
'Cause there's something
in a Sunday that makes
a body feel alone
And there's nothin' short of dyin'
half as lonesome as the sound
on the sleeping city sidewalks
Sunday morning coming down.
—”Sunday Morning Coming Down”

“GOD, IT WAS HARD ON THE people around me, like my family,” Kristofferson said. In 1960, he had married his high school sweetheart, Fran Beer, who had not at all bargained for the life of a struggling Nashville songwriter. “When I was smashed it seemed clear I would never write songs, nor a novel, nor do much of anything, so I drank more,” he told Rolling Stone in 1974. “It was very rough. When you are not doing what you think you should in life you can take it out on your old lady.” Their marriage dissolved in 1968, a year before Kristofferson’s career began to take off. “Looking back,” he said, “I was selfish. If I hadn’t been, I never would have been able to put up with the hardship I was causing other people.”

The low point came when he got fired from his job flying helicopters in the Gulf of Mexico for breaking the rule of “24 hours between the throttle and the bottle,” he says.

“Shit, though, once you get right down there on the bottom, totally broke and an embarrassment to your loved ones, and it still hasn’t killed you, suddenly it’s all easier — nothin’ left to lose, ya know?” Kris said. “But there was something taking care of me. Back when things looked the darkest, like when I lost my job in the Gulf, I thought I had hit the bottom. I had alot of expenses at the time. I owed child support, and my son had just gone in the hospital. I had a big nut to cover. And everything turned around right then.” Roger Miller, one of the hottest country singers at the time, cut three of Kristofferson’s songs in 1969. Faron Young, Bobby Bare, Sammi Smith and Ray Price also covered his work.

Johnny Cash described meeting Kris like this: “Kris came right into the control room at Columbia sweeping up and slipped his tape to June, who gave it to me. I put it with a big pile of others that had been given to me. I think I was guilty of throwing some of Kris’ songs into Old Hickory Lake. I didn’t really listen to them until one afternoon, he was flying a National Guard helicopter and he landed in my yard. I was taking a nap and June said, ‘Some fool has landed a helicopter in our yard. They used to come from the road. Now they’re coming from the sky!’ And I look up, and here comes Kris out of a helicopter with a beer in one hand and a tape in the other.”

The beer, Kris says, is a vintage Cash flourish. “Do you know how hard it is to fly one of those things? I don’t know how the hell I’d land one holding a beer.”

Beer or no beer, Johnny told Kris he’d listen to the music when he took the damn helicopter out of his yard. Kris said he’d take the helicopter away once Johnny listened to the track. The track was “Sunday Morning Coming Down.”

After that, Cash said, “I liked his songs so much that I would take them off and not let anybody else hear them.”

Cash decided to record “Sunday Morning” live on ABC for The Johnny Cash Show in 1970. He invited Kris backstage, and as they were hanging out, waiting for the show to start, the ABC censors approached Johnny, saying that the line “Wishing, Lord, that I was stoned” wasn’t going to work. They suggested “Wishing, Lord, that I was home.” Johnny paused and asked Kris what he thought. Kris said it didn’t mean the same thing. Changing it took the piss out of it, but he was sure Johnny knew what he was doing and would respect whatever Johnny thought was best.

Then Kris was escorted up to the balcony to watch the performance.

During the chorus — and you can see this on the tapes — Johnny looks up at Kris, and then, Jim Morrison-style, booms, “Wishing, Lord, that I was stoned.”

The helicopter pilot/janitor never had to punch a clock again. “Sunday Morning Coming Down” topped the charts and won the Country Music Association’s Song of the Year, edging out “Okie From Muskogee,” in 1970. That night, the outlaw hippies won.

From that time forward, Kris and Johnny were brothers in arms.

We used to drink about
a bucket of booze
To try and chase away
the black and blues
When it come the time
to pay your dues
We gave an IOU
to the devil with a dirty smile
Which he added to the growing pile
of the promises you mean to keep
The day your dreams come true.
—”The Show Goes On”

NEXT, KRIS BEGAN THE NERVE-racking process of singing his own songs.

“I’m not a performer,” he said at the time. “I mean, I do it and sometimes I like it and sometimes I hate it. There are moments when it’s almost as good as writing — when everything comes together. When the…” he paused, not wanting to sound too pretentious. “Just everything is working, you know? Like when I was playing football and we were really moving the ball forward — and you knew nothing could go wrong. Every block, every pass, every run, it couldn’t go wrong- well, it can be like that onstage when, God.” He smiled a big, shit-eating, life-loving smile. “The harmony sweeps in and holds you. It’s the same feeling I had being a part of a good team. It’s beautiful, because you lose yourself, which is the same thing that happens when you’re writing well, or doing any true creative act. You lose consciousness of yourself as an individual. That’s the great escape. It’s better than booze, my boy!”

His first album, Kristofferson, was a commercial no-show, but serious music critics noted it as the emergence of a major new force. “He is going to go a long way, and soon,” Rolling Stone predicted.

While no one writes long, grateful passages about his mellifluous voice, there is something humble, honest and profound about Kris singing his own work. Willie Nelson says, “Some of my favorite singers are not really singers, like Hoagy Carmichael, Johnny Mercer, Shel Silverstein, and Kris — but they have a way of singing that is perfect for their songs.”

In 1970, Kris was playing his own stuff at the Troubadour in L.A., opening for Linda Ronstadt, when some great reviews trickled in. The music was pushing against the boundaries and definitions of “country music,” but it was too early for people to understand that. It was Kristofferson’s looks that sparked a wildfire with the Los Angeles tabloids. Hollywood big shots were coming in every night to check out the hillbilly poet, whom L.A. papers had taken to calling the Warren Beatty of country music. Johnny Cash caught wind of some of the starlets Kris had been seen running with and commented, “We’re shitting in the tall cotton now, aren’t we, son?”

Kris was exasperated by all the talk. “People say, ‘Now that you’re a “sex symbol,” are they taking your lyrics less seriously?’ But they weren’t listening to them at all before, you know?”

Dennis Hopper fell in love with the music and started coming to the club. At an afternoon party at Hopper’s, Kris got so fucked up that he fell asleep in a grocery-store parking lot and missed the first show that night, leaving Barbra Streisand, among others, sitting idle in the audience.

When asked about his sex, drugs and rock & roll days, Kris quotes Blake: “The road of excess leads to the palace of wisdom.” It’s not clear if he’s kidding.

Everybody began recording his songs: artists as varied as Gladys Knight, Ronnie Milsap, Isaac Hayes, Elvis Presley, Carly Simon, Perry Como, the Grateful Dead, Brenda Lee, Jerry Lee Lewis, Marianne Faithfull, Percy Sledge and Bob Dylan. In 1971, he had written three of the songs nominated for Best Country Song at the Grammys that year. Three more nominations came in 1973. In the years that followed, Willie Nelson and Kris led a charge that changed country music. They elevated it. They gave it sophisticated lyrics with a mature sense of sexuality, and transformed it into a kind of white man’s soul music. Rosanne Cash says, “All his integrity was just bleeding onto the vinyl. He raised the bar for modern songwriters to a stratospheric level.”

“Personally,” says Randy Scruggs, one of Nashville’s most sought-after producers, “I feel there have been only a few that truly changed the definition of country music: Willie Nelson, Johnny Cash, Waylon Jennings immediately come to mind, as does Kris Kristofferson. Kris possibly more than anyone helped to define a new wave of music through his lyrics and his dedication to speaking out.”

“He kinda brought us out of the Dark Ages,” Willie Nelson said.

Take the ribbon from your hair
Shake it loose and let it fall
Layin' soft against my skin
like the shadows on the wall
Come and lay down by my side
till the early morning light
All I'm takin' is your time
Help me make it through the night.
—”Help Me Make It Through the Night”

SOON KRISTOFFERSON BECAME A significant player in the Hollywood film revolution of the 1970s. Kris accompanied Dennis Hopper to Peru to score his film The Last Movie, and did his first bit of acting, “’cause I knew how to ride a horse.”

Kris had gotten back from Peru and was performing at the Big Sur Folk Festival in Monterey, California, when he heard that Janis Joplin died. She and Kris had been lovers for a short time.

“We were both in love with what we were doing more than anything else,” Kris said. “We were in love with the music.”

When I first met Kris on the film Chelsea Walls, shooting in New York’s bohemian mecca the Chelsea Hotel, he told me, “I met Janis in the elevator here, and we were both naked in about 15 minutes.”

Kris had sung “Bobby McGee” for her, but he didn’t know she had recorded the song in 1970 until after she died, when the producer from her label played it for him after a party held in her honor. Kris went off by himself and listened to it over and over. He couldn’t believe that she had recorded it, how fucking brilliant the track was and that Janis was gone. Soon the song was a Number One single and the anthem of a generation. The record company clamored for another solo album. Simultaneously, the impression he had made on those Hollywood big shots began to reverberate.

There are many musicians who have dabbled in film and actors who have tried their hand at a recording session. But only Frank Sinatra has done both on the level that Kris has, and with Sinatra it was different: Sinatra was a showman. Kris is a poet who sometimes sings and acts extremely well. “For me it was about intensity,” Kris tells me, “wanting to do something, anything good! To be a part of any creative act is exhilarating. To get out there and tell the truth — through songs or through performance, it doesn’t matter. I’m a good writer but I’m not a singer like the people I admire.

“I feel about my acting the same as I do about my performing. I’m sure as hell no Laurence Olivier. When it works, I feel blessed that it does, but it works just when I’m being as honest as I can be with whatever it is I am playing.”

One of his early movies was Martin Scorsese’s 1974 gem Alice Doesn’t Live Here Anymore. “Back then, you could try anything,” Scorsese tells me. “There was an atmosphere, and Kris — he just embodied the feeling of that moment in time ’cause he wasn’t solely an actor, that’s what made it. He crossed genres. He was being covered by everybody! And, you see, that’s what people wanted from their actors back then. They expected more. Everyone was experimenting. It wasn’t just the way he looked — it was the way he moved, his voice. His presence allowed the audience inside the picture. He made it look so easy.”

People usually think of great acting as some kind of exotic metamorphosis. Consider Robert De Niro in Raging Bull or Philip Seymour Hoffman in Capote. Those are deeply moving, multilayered, staggeringly well-crafted performances — magnificent examples of what I like to call “third-person acting.” But there is another kind of acting that is difficult in its own way, what I think of as “first-person acting.” Paul Newman was a perfect example. Life seemed to move through him. It was not a performance. He was those people.

At his finest, Kris has achieved real moments of grace onscreen. The simplicity of Bob Dylan and Kris bullshitting by the side of a dusty Mexican cantina in Sam Peckinpah’s Pat Garrett and Billy the Kid. We are watching the poet youth of America claiming the country by seizing its most iconic art form, the Western, right out of John Wayne’s and Glenn Ford’s hands.

That film, about friendship, betrayal, capitalism, growth and deterioration, is as defining of America’s bravado, yearning and sadness as anything put on film, and Kris’ thumping, honest heart drives it.

I ask Russell Crowe about Kristofferson the actor. “The magic in Kris’ performances for me,” he says, “is his inability to hide the truth from himself. From time to time, he may fool other people, but as painful and inconvenient as it may be, he can never not see himself and the world around him just as it is, and he is compelled to let that truth be known.

“My favorite film performance of Kristofferson’s remains A Star Is Born,” Crowe adds. “A songwriter who writes about washed-up has-beens plays one in a movie that was the zenith of his career. There is delicious irony in that.”

A Star Is Born ushered Kris to the pinnacle of mainstream pop culture. He captures all the magic, self-indulgence, magnetism and narcissism of a giant star staring his own meaninglessness straight in the eyes. The movie was drippy enough to be a smash hit. The number-two-grossing movie of 1976 (behind Rocky), it made women of all ages weak-kneed for the 40-year-old songwriter.

Here’s how the writer and film director Cameron Crowe ended his 1978 Rolling Stone cover story on Kris:

“Can you — Kris Kristofferson — do it all?

“I have a clear image of Kristofferson yelling back his answer through a mouthful of ice.

“‘Look at me! I can go from Donny & Marie to Sam Peckinpah to Radio City Music Hall in one week. I’m just a ramblift guy… with rangy hips…. ‘Course I can do it all!'”

If someday you wake up in a world
that's turned on you
And nobody answers when you call
Hey, think of the easy dreamer
who believes in you
The bigger the fool
the harder the fall.
—”The Bigger the Fool (The Harder the Fall)”

KRIS AND HIS NEW WIFE, RITA Coolidge, were performing to sold-out crowds, traveling the world as a power couple and winning Grammys. Kris even scored a Best Actor Golden Globe for A Star Is Born. And then came Heaven’s Gate.

“I was in a place where I’m making as much money as anybody workin’ in the movies,” he says. “Then, when the movie comes out – I couldn’t get arrested. Well, I could get arrested, but that was about all I could do.” He kind of half-laughs.

How badly Heaven’s Gate was received cannot be exaggerated. It was Michael Cimino’s first film after the acclaimed The Deer Hunter, and every A-list actor wanted the lead role, and Kristofferson got it.

The filming of Heaven’s Gate ran into a myriad of problems: The budget ballooned to such an incredible degree that it became one of the most expensive movies ever made, and rumors were that the money was funding the hard-partying lifestyle of the director, east and crew more than the production of any Cleopatra-like set. The film was dead before anyone saw it. At the 1980 Cannes Film Festival, one of the studio executives warned the press, “Unless control is taken from the creative people, our industry is headed for disaster.”

Kris responded, “So who do you give it to, the uncreative people?”

“You have to understand,” Scorsese tells me, “by the time Heaven’s Gate came out, United Artists had changed hands, and the people left in charge there were just trying to handle what they had. Raging Bull came out in November and Heaven’s Gate two weeks later — and the Seventies were put to rest in one night. We had the rug pulled out from underneath us. The critical establishment ended that decade by making an example out of Heaven’s Gate, eviscerating the film and everyone associated with it and what it represented — a Western with anti-American sentiment. They’d had enough. They were done supporting individual expression in the movies. The power was given back to the marketplace. Your value was now determined by how much money you made. In the Seventies we would have thought that was crazy! We thought culture needed to be nurtured. But in the Eighties, not anymore. Why take a chance on individual voices?”

I ask Scorsese why he thinks Kris seemed to stop so abruptly as a force in mainstream culture.

“It wasn’t just Kris, you understand, the whole climate changed.”

Seeing the film a quarter-century later, to me, Heaven’s Gate brims with beauty, power and artistry. Kris is the film’s workhorse, carrying its weight effortlessly.

Got a song about a soldier
ridin' somewhere on a train
Empty sleeve pinned to his shoulder
and Some pills to ease the pain
Started drinkin' in El Paso
he was drunk in San Antone
Tellin' strangers who were sleeping
how he hated going home
Just a simple song of freedom
he was never fighting for
No one's listening when you need 'em
Ain't no fun to sing that song
no more.
—”Broken Freedom Song”

AS REAGAN TOOK THE OATH OF OFFICE, the country began to embrace a different set of values and needed a new set of idols.

“Don’t look back, something might be gaining on you” is a Satchel Paige quote Kris put on the back of one of his early albums. Whatever that “something” was, it had caught up with him. Everything went to hell.

“What is even more difficult than failure,” he tells me, “is when you are perceived as a ‘success’ and you are failing.”

There are tales of Kris drinking two bottles of whiskey a day, rumors of womanizing and drug abuse. His records stopped selling, gigs were canceled, ugly gossip swirled around his divorce from Coolidge, the critics who had been so warm became cruel, friends and collaborators died, his agent and his label dropped him. Kristofferson didn’t field another serious offer to act for more than four years.

“It’s rare to have that kind of opportunity, to face that kind of transition, to go from the absolute pinnacle of success to being unhireable,” he says. “And my personal life was falling apart at the exact same moment. My marriage to Rita Coolidge got hit from behind by a truck. All of a sudden, I was a bachelor father taking care of our little girl. People would come up to me and say, ‘Didn’t you used to be somebody?’ I was in a pretty dazed condition.”

Hank Williams died at 29, Woody Guthrie at 55, Townes Van Zandt at 52. One of the remarkable things about Kris is that he lived so fast, burned so bright, crashed so hard, and survived.

He met his third wife, Lisa Meyers, at a gym. One day she asked him if he wanted to go for a run. He said, “Listen, I get up in the morning and take my little girl to school and I pick her up when school is over, and that’s all I can handle right now. I have a very complicated life.”

She said, “I was just asking you to go on a run – I wasn’t talking about changing your life.”

But that’s what she ended up doing. “I had a lot of bad habits,” Kris said, “but Lisa had a great right cross.”

In the Eighties, when times were the hardest for Kris, he just marched on, writing and singing beautiful songs about Sandinistas, Jesse Jackson, Vietnam vets, César Chávez and migrant workers, the evil of money, the futility of war, children, marriage and spiritual longing. As accomplished as these songs were, folks still liked the tunes about “gettin’ by high” a bit better and few paid attention.

“I was so taken with what I was doing politically and trying to bring people’s attention to what our country was doing down in Central America, trying to use what I’d learned, that I didn’t know how far from the mainstream I’d fallen,” Kris recalls. “I was driving up through Texas one time and heard the guy on the radio refer to me as ‘washed up.’ I’d had no idea. I was in a blessedly stupid state of shortsightedness, not allowing doubt to paralyze me.”

Staring at the tabloids, people wonder why celebrities spin off into eccentricity and madness. (As someone who encountered fame at the age of 18, I’ve given this phenomenon considerable reflection.) It has to do with isolation — if you put a human being into any isolation chamber, they will hallucinate. Celebrity is a form of isolation. You are cut off from your community, people react and respond to you in an altered fashion. They give you exemptions from the normal rules of social engagement, they indulge you — and then they resent you for it. You live behind a glass wall — the more people stare, the more alone you feel. Then a snake of madness and megalomania creeps into even the most stable mind. The more fame, the more poison you swallow. The cure, the healing elixir — in my experience — is friendship. Kristofferson, luckily, took the time, put in the hours, made the effort to earn a shitload of friends.

Even when people were protesting his appearances and Kris would be met with a chorus of boos when he performed, Willie Nelson continued to invite Kris to join him onstage. Eventually, Willie was the one who brought Kris back into movies with Songwriter, for which Kris’ score was nominated for an Academy Award in 1984. Then Willie, Waylon Jennings, Johnny Cash, and Kris started a band called the Highwaymen. The group earned a Grammy nomination in 1990.

“Audiences adored them,” says Lisa Kristofferson, “but they couldn’t know how great those men really were together behind the scenes. It was a decade of rolling laughter and love. John and Kris’ last words to each other were ‘I love you.’ Same to Waylon. That’s rare for men, and it was real.”

“Me and Kris?” Willie Nelson writes me from the road. “I think we are about as close as friends can be. I think we understand all we need to understand about each other.”

Love is the last thing to go
Love is the reason
we happened at all
And it paid for
all the damage we done
And it bought us
the freedom to fall into grace
On our way to our place in the sun.
–“The Last Thing to Go”

IN THE MID-NINETIES, KRIS the movie star re-emerged as a powerful character actor, working with some of the finest contemporary directors: John Sayles, James Ivory, Tim Burton, Guillermo del Toro, Richard Linklater.

A 60 Minutes interview in the wake of his “return to form” performance in Lone Star in 1996 shows Kris standing in his front yard in Hawaii, relaxed and cavalier about all the renewed attention. Kris describes his modest home as “an old samurai poet warrior’s house.” He takes a long, thoughtful pause. “I’m his groundskeeper,” he adds. He pauses again, considering the idea more deeply. “And I get to sleep with his wife!” Then he characteristically explodes with laughter.

Most movie fans today know Kris as the grizzled vampire killer in the Blade films. As an actor who has done some numb-nut B-movie work myself, I can say that Kris’ performances in the first two Blade films are pitch-perfect. He’s the grounding wire running through those two popcorn movies.

In James Ivory’s A Soldier’s Daughter Never Cries, he delivers what may be his finest work ever as an actor. Lisa Kristofferson tells me Kris had internalized that character so deeply that she was afraid when he went to the set for the final death scene that he might actually let his spirit leave his body and die. Scorsese notes that “his performance in that film is like that of an older Jimmy Stewart or Gary Cooper. There is truth when he speaks. You sense that he is genuine. He has that big, iconic American face — with the soul of a poet.”

When I directed Kris in 1999, he played a recovering alcoholic named Bud. A pivotal scene has him pick up the bottle again and then call an old lover. On the page it Was a seven-minute-long monologue. I had picked a location so that I could play the whole speech in one long shot. I had a Godard-inspired idea where Kris would walk from room to room, talking and drinking, switching lights on and off, and then at the end of the speech he would arrive back in the same place the shot had begun. It was a complex maneuver, and I was excited about it. I explained the idea to Kris.

“Have you ever had a serious problem with alcohol?” he asked in his gravelly voice.

“Ahhh, no.”

“Uh-huh,” he said. “Does Bud have a serious problem?”

“Yes,” I said.

“Well, let me tell you something. I’ve had a serious problem with alcohol. And if I was gonna fall off the wagon and crack open a bottle of Jack, I sure as shit am not gonna walk around my room like Chatty Cathy, flippin’ on and off lights.”

“What would you do?” I asked.

“Well, if I was gonna fall, I’d fall hard and sit my ass down, snap that seal and drink the whole goddamn bottle.”

“Hmmm,” I paused, considering the effect of abandoning my fantastic shot.

“Let me put it another way,” Kris added. “This speech is extremely long, and we are gonna be lucky today if I remember it at all. But if I gotta pour whiskey, and walk, and flip switches, and not bump into a moving camera, and remember all these goddamn lines, we’re dead in the water.”

I laughed and set the camera up straight on him — simple as can be — and he delivered. His performance is electric.

Why me, Lord?
What have I ever done
to deserve even one
of the blessings I've known?
Tell me, Lord, what did I ever do
that was worth loving you
Or the kindness you've shown?
—”Why Me”

“WHY DO YOU THINK YOU DIDN’T SELF-destruct like so many others?” I ask Kris. He was just sitting still, answering my questions slowly and deliberately. Always a touch short of breath, he seems like a man who’s survived a shotgun blast to the chest – or more likely smoked 40 trillion cigarettes.

“I guess I don’t really understand how it happened that I have lived this long. Probably doesn’t have anything to do with me, except that my desire for life is strong enough to force me to find some kind of discipline. Some people get bowled over by failure, and can’t pick themselves back up again, you know?” He looked at me, his crystal-blue eyes more piercing than ever, now that his lids hang and shadow them.

“Even with an experience like Heaven’s Gate, as negative as that was, I mean, the way it was received,” he continues. “There was still so much good about it for me. Cimino is gifted and passionate, and the film woke me up to an ugly piece of American history — when the cattlemen’s association started wiping out civilians with the backing of the U.S. government. It was money they were killing people for. I became aware of this about the same time that the U.S. was going down and killing people in Nicaragua — I learned about all that on that movie — so there were a lot of positive things that came out of that experience as far as my education.” He pauses. “I was lucky,” he says in a warm voice, “that the old creed of imagination that had got me there in the first place didn’t get killed in the process. Through it all I could still find reasons to write and go out and sing. I became unmarketable in music and film at the same time — but I was still experiencing enough joy just from the creative act.”

When he said that, I realized why I had wanted to make a documentary about Kris. When I first met him, I wondered what it felt like to have stood center stage in the heat of the spotlight and then to have watched the beam move on.

“I know there are people out there that say that the fact that I got to be a movie star hurt my writing. Tom T. [Hall] once said, ‘One of my favorite songwriters died of overexposure.’ And he meant me.” Kris raises his eyebrows. “I don’t believe it. I think I was writing to the best of my abilities all the time, every album was how I felt about what was going on in my life and the world at that given time. I never felt success had made me worse. I never felt failure helped anybody. I don’t think if you’re a serious artist you’re going to be more or less lazy depending on your level of success.”

We carried on for a while discussing Bob Dylan and Emily Dickinson; one who has maintained meteoric fame throughout his life and one whose life passed in obscurity — but both fully realized artists. “If you’re serious about what you’re doing, all that other shit just fades to the background.” He takes a deep, long, difficult breath. “But I do wish I could take all the good moments of my life and spread ’em out like one every other year. It seems to me that ‘good times,’ like the ‘hard times,’ come in bunches.”

“Did you ever make up with your parents?” I ask.

“Before he died, my father told me that ‘I’ll never understand what you have been doing with your life, but I do understand your need to do it.’ You see, he had really wanted to be a pilot, and he understood my drive – nothing would have ever stopped him from flying.”

“What about your mother?”

“We were good.” He pauses and grins, remembering a story. “She and Johnny Cash came to this tribute thing they were doing for me over at Pomona College, and you should’ve seen my mom hugging and fawning over him. It was great.” It seems in the presence of the Man in Black, his mother had forgotten all about her earlier admonishment that “nobody over the age of 14 listens to that kind of music.”

“I’ll tell you a story,” Kris says. “After June passed, they were having a service where you view the corpse, all the people, friends and guests were there. John was sitting over in a chair right by the coffin, so I went over and sat next to him, and people were coming by, shaking his hand and paying their respects to June. This one guy came over and when he saw me, he said, ‘Oh, Kris Kristofferson! You are one of the best singers I’ve ever heard!’ He went on and on and shook my hand and left. As he walked away, John says, and you got to realize where John is at this moment in time, John leans over and whispers, ‘Well, that’s one.’ Kris laughs at the memory. “In the depths of his despair, he could still take the piss outta me!”

“I’ve thought a lot about Kris,” Rosanne Cash says. “His humility is a powerful quality, but to me, it just supports what I think is his greatest attribute: his truth-telling. He is an oracle. Kris tells the truth, all the time, about everything… except himself, which is where the humility part gets muddy. He can be too self-deprecating and dismissive of his own greatness. If you can get past the tangle of that, then you see the truth at the center, and there is where the power is for me. The narrative of his life has been one of ever-increasing integrity. I observed his friendship with my dad, and although Kris would not say this, I think Dad learned from Kris. Not that my dad didn’t have a refined integrity- he did — but he had more problems living it out in day-to-day reality than Kris does.”

“Love to me is the only answer to what’s going on with the world,” Kris said. “The kind that you feel unconditionally for your children.” (Kristofferson now has eight kids from his three marriages.) “And if you work at it, you can get to where it includes others too…. If you were to attain the highest state, I guess you would love everybody.”

Talking to Kris today, you get the feeling that what he really wants for Christmas is for the Holy Muse to see fit to share with him one more song that could change the world. While he waits, he wants to write his memoirs, but he seems to fear that would be admitting he’s old. His expectation of himself is tremendous, and I would guess that Kris dances regularly with the “Black Dog” of depression.

“We always thought he’d do something big,” recalled a classmate from college. “He was president of the freshman class, the sophomore class. He was president of every class; of the debating team, the writing club, the football team, baseball. Kris was the best-liked, most respected boy that school ever saw. But there was always something else about him, nice as he was. There was a sadness.”

The record producer Don Was once said that Kristofferson was the most intelligent person he’d ever met: “That kind of enhanced consciousness can be a psychic burden to the poor soul who has got to live with it 24 hours a day. But it sure makes for some great music.”

WHEN KRIS GETS UP TO LEAVE MY PLACE, I ask him if he has ever done a play.

“Nope,” he answers.

“Would you want to?” I had a specific production in mind.

“Definitely,” says the 72-year-old man.

I watch Kris dash out of my apartment and hustle down the street through the rain, having refused an umbrella, his ratty old cowboy boots splashing through puddles. I thought of a Eugene O’Neill line: “People who succeed and do not push on to a greater failure are the spiritual middle-classers.”

Kris’ wife, Lisa, had been with him when he arrived for our interview. On her way out she had referred to him as her velveteen rabbit.

“I ain’t a goddamn rabbit!” Kris had bristled as any man would at getting called a goofy pet name in public. Smiling at the memory of that exchange, I went to my son’s room and found the old Margery Williams book The Velveteen Rabbit.

“What is Real?” asked the rabbit one day. “Does it mean having things that buzz inside you and a stick-out handle?”

“Real isn’t how you are made,” said the Skin Horse. “It’s a thing that happens to you…. It doesn’t happen all at once. You become. It takes a long time. Generally by the time you are Real, most of your hair has been loved off, and your eyes drop out and you get loose in the joints and very shabby. But these things don’t matter at all, because once you are Real you can’t be ugly, except to people who don’t understand.”

Reading those lines, after spending time with the man, I find Lisa’s nickname well-suited. Her husband has a full head of hair and is still dastardly handsome, but he’s worn down along the edges and yet somehow more alive than ever. Passed around and over-handled by the public, Kris has been called many things: hick, intellectual, playboy, husband, radical, soldier, hippie, class president, outlaw, loser, star, washed up, legend. The Texas boy whom everybody had a plan for, the Army captain who grew his hair long, moved to Nashville wanting to be Hank Williams, walked into a recording studio wanting to be Johnny Cash, and went to Hollywood wanting to be Glenn Ford. He has now been loved so hard, worked so long and burned every dream to smoking ashes, so much so that he’s not wanting at all. He just is. Authentic. Genuine. Real.

I got lucky
I got everything I wanted
I got happy
There wasn't nothing else to do
And I'd be crazy
Not to wonder if I'm worthy
of the part I play
In this dream that's coming true.

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