The Silver Tongued Devil and I

With a new album, a command performance at Disney Hall, and three films in the can this year, Kris Kristofferson has got nothing to lose. A lifelong fan takes him back to where his legend began

Kristofferson is sitting on the edge of the stage at the Troubadour in West Hollywood, remembering. Nearly four decades ago, he’d arrived at the landmark club to play his first gig. The years leading up to that June night had been full of struggle, but just eight days before, music critic Robert Hilburn had raved about him in the Los Angeles Times. A songwriter “of major proportions,” Hilburn had called him, singling out “Me and Bobby McGee” and “Sunday Morning Coming Down” for special praise. 

On June 23, 1970, and for the next five nights, Kristofferson took the stage with his acoustic guitar and his trademark ragged voice and sang his heart out. Among those who showed up to listen were Barbra Streisand, John Lennon, and director Sam Peckinpah, who in a couple of years would cast him as Billy the Kid. Linda Ronstadt was there, too—she was the headliner. For Kristofferson, then 34, things would never be the same.

“Looking back on it, I can’t believe I had the audacity to do it,” he tells me now, turning his head to take it all in: the dark wood bar, the balcony, the flight of stairs that lead to the dressing room. His bass player, he recalls, nodding toward the spot on the stage where Billy Swan had stood, was still learning his instrument. His guitar player, Dennis Linde, was so nervous that he stared at the back wall the entire night.

“It was amazing that we survived it. It was really jumping into the deep water,” says Kristofferson, running a hand through his full head of gray hair. He is wearing a short-sleeved black shirt and black jeans, and as he talks he seems to relax, enjoying the midday calm in a place that’s usually packed. “If you were gonna play here,” he says, “it was really important. It was where it was happening. Instead of being unemployed, all of a sudden I was getting away with murder!”

Damn handsome at 73, Kristofferson has a new album, released in late September. Closer to the Bone explores further the territory he laid out in 2006 in This Old Road. Both were produced by Don Was and feature poignantly reflective songs. In “From Here to Forever” he tells his kids (he has eight of them): “And darlin’ if we’re not together / There’s one thing I want you to know / I’ll love you from here to forever / And be there wherever you go.” In a song about Johnny Cash, “Good Morning John,” Kristofferson praises his late friend for overcoming addiction. There’s a hidden bonus track, which Kristofferson introduces on the CD by saying, “Here’s the first whole song I ever wrote. Eleven years old and well on my way.”

I was only two years older than that when I became a Kristofferson fan. I saw A Star Is Born, the movie that made him a sex symbol, nine times in 1977. But my junior high choir teacher set me straight: Its soundtrack wasn’t Kris’s music. To be a true fan, she said, I needed to check out the songs he had actually written. I did. His 1977 compilation Songs of Kristofferson was the first record album I bought with my own money. I still have it. That same year I went to my first concert: Kristofferson and then-wife Rita Coolidge.

Although I grew up in Texas, country music wasn’t what my family listened to, and I thought the pop country on the radio then was crap (still do). But hearing Kristofferson, I was fascinated. His lyrics painted vivid pictures in my mind. Even at that age I could feel all the heartache and see all the bar stools. (Only later would I appreciate the heat he added to the genre—as another songwriter put it, Kristofferson was the first to bring country music into the bedroom.)

The first song I memorized was “The Silver Tongued Devil and I.” Then came “The Pilgrim Chapter 33,” which begins with Kristofferson talking about the people who inspired it, among them songwriters Chris Gantry, Bobby Neuwirth, Jerry Jeff Walker, Funky Donnie Fritts, and Ramblin’ Jack Elliott. Just the sound of those names made me want to know: Who were these people?

I tell Kristofferson that I remember my exact location in the Houston Summit when I saw him—Section 122. Row B. Seat 1. Ticket price $7.85. (I kept the stub.) “Wow,” he says, blue eyes amused. “Was it any good?” (I choose not to tell him that after he and Coolidge did their last encore, I stole his can of Tab from the stage.)

Kristofferson’s songs at their core are poems about everyday life, about heroes, losers, sinners, and saints. He writes with a raw wisdom that never seems preachy or pretentious, telling simple stories that you realize later aren’t so simple. The titles alone hint at how much he’s trying to say: “Loving Her Was Easier Than Anything I’ll Ever Do Again,” “From the Bottle to the Bottom,” “Help Me Make It Through the Night.” If there’s one dominant theme, it’s gratitude. “Why me, Lord?” he asks in the song “Why Me?,” which he recorded in 1972. “What have I ever done / To deserve even one / Of the pleasures I’ve known?”

On “The Wonder,” a song from the new album, that deep appreciation is undiminished: “I swear to be thankful the rest of my days / And worthy whatever I do / For the chance I was given / To live and believe / In the love and the wonder of you.” To me he says, “The way I feel about it, I’m lucky to be standing around here making a mark on the mirror.”

When I ask which songs were inspired by L.A., he doesn’t bother to name a title. Instead he starts singing. “Shot down and sinking fast on Sunset Strip,” he begins, looking pleased with himself, “Holding onto something in my head / Everything gets heavy when you’re losing your grip…” Here he laughs, muttering, “That’s my favorite line,” then continues, “Nothing looks as empty as a motel bed.”

It’s “Smile at Me Again.” His voice is weathered—but right on key.

Before he ever sang a word in front of an audience, Kristofferson already had an incredible biography. Born in Brownsville, Texas, he went to high school in Northern California, then studied creative writing at Pomona College, where he graduated Phi Beta Kappa. He played football and rugby and boxed competitively. After college he went to Oxford University as a Rhodes scholar. At 24, newly married, he needed a job, so he followed in the footsteps of his father, an air force general, by joining the military.

An Airborne Ranger, he trained as a parachute jumper and helicopter pilot. Then the army offered him a post teaching literature at West Point. The week he was to take the job, he changed course, moving his family to Nashville. He wanted to be a songwriter. The decision would cost him his marriage and, for a time, damage his relationship with his parents.

In Nashville, a tight community of aspiring songwriters became Kristofferson’s new family. They lived together, staying up night after night, passing around a guitar trying to “shoot their best shot,” Kristofferson recalls. Alcohol and pills kept them going. The camaraderie was genuine: Everybody wanted everyone else to succeed. Songwriter Mickey Newberry told Roger “King of the Road” Miller about Kristofferson’s songs, and Miller would later record “Me and Bobby McGee.”

“To have Roger Miller cut your song was like having Shakespeare do your play,” Kristofferson says.

At the time, Johnny Cash’s hit TV show was being filmed locally, and it booked the kinds of acts Kristofferson hoped would take an interest in his music. He hung around backstage, pitching to anyone who’d listen. When it came to pitching to Cash himself, though, Kristofferson did something far more dramatic. Having gotten nowhere with the usual entreaties, he famously landed a helicopter in Cash’s yard.

“I wish to God I’d never done that,” he tells me, but he doesn’t really. After all, the gamble paid off. Cash recorded “Sunday Morning Coming Down.” Kristofferson would later name his sixth child Johnny Cash Kristofferson.

The Cash and Miller covers, among others, gave Kristofferson momentum. He was not yet a performer, but Monument Records signed him anyway, and he went on tour. The Troubadour was his first stop, and the place was packed. “He looked kind of disheveled, as if he’d been up all night,” Hilburn says. “That’s just the way Kris always looked in those days.” Then when he sang, “the room just got quiet,” the critic continues. “You could feel that people knew they were hearing someone special.”

As it often does, success led to excess. One night during the Troubadour run, Kristofferson was arrested for drunk driving just blocks from the club. Another night he missed the first half of a performance because he had overindulged at Dennis Hopper’s house and fell asleep in his car. Hopper, hot off the hit Easy Rider, had given Kristofferson his first film role, putting him in 1971’s The Last Movie (to which Kris also contributed songs).

After the Troubadour, Kristofferson hit the road, and life became a blur. There were love affairs with starlets and singers (Streisand, Ronstadt, Janis Joplin). There was enormous fame (the bathtub scene in A Star Is Born set a new standard for onscreen chemistry in the ’70s; steamy images from the set of The Sailor Who Fell from Grace with the Sea appeared in Playboy). There were Grammy Awards and collaborations with his heroes (he, Waylon Jennings, Willie Nelson, and Cash became the Highwaymen). There was sobriety (he stopped drinking in 1976). There was loss (his second marriage, to Coolidge, ended in 1980, the same year he starred in Heaven’s Gate, generally considered to be the biggest box-office flop of all time).

Casting directors were gun-shy, and he didn’t work in movies for years. But he kept writing songs, and his life began to settle down. He married his current wife, Lisa Meyers, in 1983.

Is it easier to write a song at night or during the day? “As long as my eyes are open and I’m awake, it doesn’t matter,” he says.

Drunk or sober? “The liquor will loosen you up a little bit. Sometimes that’s better, but sometimes it works against you.”

When you’re in love or when you’re brokenhearted? “Oh,” he says, his voice mischievous. “Anything’s easier when you are in love.”

In Cornflakes with John Lennon, Robert Hilburn’s new memoir that’s out this month, the music critic tells a story about a conversation he had with Janis Joplin not long before she died. She was coming to Los Angeles to record an album, and “she’d found some new songs by a new writer named Kris Kristofferson.” When Hilburn told Joplin he loved Kristofferson’s work, “that ignited a competition between the two of us over who could get the most excited about him.”

Joplin had a trump card, Hilburn writes. “He’s not bad in bed, either,” she said. But her real interest in Kristofferson was musical. She told Hilburn she wanted to change her image from screamer to singer, and she felt Kristofferson’s songs could make the difference. Joplin “talked about ‘Help Me Make It Through the Night’ and sang a line from ‘Sunday Morning Coming Down,’?” Hilburn recalls. “I got the impression she might do a whole album of Kris’s songs.”

Turning to Kristofferson now, I tell him about Hilburn’s story. It’s clear that he hasn’t heard it. He grows unusually quiet. Gently I ask him, Which of his songs would he have liked to hear Joplin sing? “Oh, any of ’em,” he says, his voice barely a whisper. “I have never thought of that. I’d have to find something worthy of her.” For several moments he is lost in thought. “I’ve got mixed emotions on that. I’m really honored, but”—he pauses—“it didn’t happen.”

Kristofferson didn’t know that Joplin had recorded “Me and Bobby McGee” until after she overdosed in Hollywood in 1970. “I was at the motel where she died,” he says, “and the producer of her record said, ‘Come by the office tomorrow—I wanna play you something.’?” He whistles now, thinking back on the moment he heard her voice sing his words. “I remember it was like getting hit in the head with a sledgehammer,” he says. “I listened to it as long as I could.”

He’ll need to do more remembering if he’s going to write a long-planned—and long-avoided—memoir. Some of the ground he knows the book will need to cover: the revival of his acting career in 1996 with the release of John Sayles’s Lone Star. Since then he’s gotten steady movie and TV work in projects as varied as the Blade vampire films and the character-driven drama A Soldier’s Daughter Never Cries. He has been in three films this year and has four more in the works.

But songwriting will always be first in his heart, and he’s still at it. He and his wife have lived on a 25-acre ranch in Maui for almost 20 years. Kristofferson spends a lot of time there on the tractor, tending to his lawn. “Most of the songs that come now,” he says, “are probably to the rhythm of that motor.”

At 13 I didn’t know that Kristofferson was revolutionizing country music—just like I didn’t know that he was turning me into an Americana music fan (OK, freak). The last time I saw him perform, at the Stagecoach Music Festival in 2007, the enormity of the debt I owed him became clearer. He was older. So was I—and by now I had lived some of the hope and heartache that I’d heard him sing about in 1977. I’d spent my own couple of decades playing keyboards in bands. As always, his poetry got to me. I was just so happy he was around to sing it. I’m woman enough to admit: I wept through his entire set.

As our time in the Troubadour winds down, I am trying to better understand the sources of his own inspiration. I ask him what prepared him more for a songwriting career—being a boxer or being a Rhodes scholar? “Both,” he says at first, taking the easy way out. When I protest, he offers this: Oxford taught him about poets, but boxing taught him about life. “I had no idea who William Blake was at the time,” he says, explaining the importance of being exposed to the classics. “But I think maybe the lessons from boxing were more basic. If you never gave up, you never really lost. And if your heart was not in it, get out of it. If you never admit defeat—unless you are counted out, and there’s no question about it—then you always have a chance. If you pursue it—faithfully.”

I tell him that one of my mottoes is the line he wrote when I was a kid: “I’d rather be sorry for something I’ve done than for something that I didn’t do.” He says it’s his motto, too. So is there anything he’s sorry he did? “I’m sorry I’ve inadvertently hurt people, and I’ve been in jail a few times.” Any regrets about something he hasn’t done? The memoir, he says. He wishes he were further along. “I’ve been avoiding it, because it’s kinda like saying, ‘OK, this is it.’ But I realize now that if I don’t start, I’m going to forget everything.”

I encourage him to buckle down. You know people will want to read it, I say. “Probably…and I hope that it would be well written. I’ve always thought of myself as a writer who was lucky to be a performer,” he says. “I found out I was good at some things I didn’t know about, like acting, and I found my limitations and learned to live with them, sometimes more comfortably than others.”

We walk toward the bar, where the folks from the Troubadour are waiting with a head shot they’ve removed from the wall. Will he sign it? As he picks up the pen, I see my chance. I take my treasured first album out of my bag and put it on the bar. He winces a bit when he sees his face 30 years younger, and on a cover worn with the years. But he signs with grace, taking time to make sure he spells my name right and signing off with one word: “Peace.”

I walk him outside. Behave yourself, I say. “Don’t you be telling me what to do,” he says, his eyes twinkling. I say I’ll be in the audience when he plays Walt Disney Concert Hall on November 1. He tells me to come backstage.

Just try to stop me.

Photograph by Marina Chavez