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  But nothing worked commercially. As Chet once said in reference to Willie, “With a record company you can have a whole roomful of people who all put their heads together and grind away at a problem and still come up with the wrong answer.”

  Songwriter Billy Swan often saw Willie play at the Boar’s Nest, a sort of artists’ refuge with brown bottles and empty beds that local barmaid Sue Brewer arranged in her home on Eighteenth Avenue South. Swan often pondered the singer’s stagnation. One night, he sat on the floor while Willie towered above him, “like he were a guru, a maharishi or something, and we just listened to him do those wonderful songs in the way only he can do them. Everyone in this town knew that his guy was great. He was not like anybody else.”

  KRISTOFFERSON WOULD HAVE traded his Ranger School tab for Waylon’s and Willie’s RCA deals, but while those men struggled to find the right sound in the studio, he traipsed the sidewalks of the West End, haunting barrooms and publishing houses, in search of his elusive break. He had signed with Marijohn Wilkin and moved his family into a small house at 3525 Byron Avenue, on the edge of the West End. Eager to pick up where he had left off on his first visit, he worked on economizing his rambling verse and splashed into the Nashville fraternity life. “I suddenly felt like a fish that had gotten back in the right water,” says Kris.

  One of his best pals was Billy Swan, the Willie Nelson fan who had arrived in Nashville with serious credibility. In 1962, at the tender age of twenty, Swan had watched Clyde McPhatter take his “Lover Please” to number seven on the pop charts. More thrilling to Swan’s peers, though, may have been his stint as a gate guard at Elvis Presley’s Graceland. Or that he was arrested on his first night in Nashville.

  When Swan hit Nashville in 1963, he immediately drove down to Tootsie Bess’s honky-tonk bar on lower Broadway, near the Ryman Auditorium. All of the songwriters hung out there, and Swan was anxious to meet them. “At about twelve o’clock it was shoulder to shoulder and I’m drunk and I hear, ‘Arrest her,’” says Swan. “And I turned around and they’re arresting Tootsie, something about serving a minor. The undercover guys were there. The first thing out of my mouth was ‘You can’t arrest her.’ They said, ‘Take him, too.’ So they put me and her in a paddy wagon and took us down to jail, and we went before the judge. He didn’t even look up when he said, ‘Spend the night in jail.’ I stayed up all night, afraid to lie down. I didn’t even know where in the hell my car was. It was a Sunday morning, however. I found it in the back of the Opry parking lot, sitting there all by itself.”

  Lower Broadway in the 1960s. Note the sign for Tootsie’s.

  Courtesy of Metropolitan Government Archives of Nashville and Davidson County

  Kristofferson joined Swan on future adventures, while both continued to struggle musically: Swan to repeat the magic of “Lover Please,” and Kristofferson to win his first hit. It finally happened for Kristofferson when Dave Dudley—known best for paeans to the truck-driving life like “Six Days on the Road”—recorded Kris’s “Vietnam Blues” in 1966 and took it to country music’s top twenty. But Kristofferson still needed full-time work to pay the bills, so over the next four years, he worked a variety of jobs: ditch digger, carpenter’s assistant, and bartender. Billy Swan even got him a job at Columbia Records studio on Sixteenth Avenue South as an engineer’s assistant. Swan had worked there after stopping by to pitch songs and play Ping-Pong with studio musicians. But he was leaving for another job right in the middle of Bob Dylan’s historic Blonde on Blonde sessions in February 1966. The studio manager asked him to keep an eye open for a replacement. “So I walk out of his office,” says Swan, “and say bye to Polly the secretary and as I was pushing the door to go out, Kris was pulling it to come in. And the first thing out his mouth was ‘Do you know where I can get a job.’ I said, ‘Yeah, I just quit mine.’ And we went back into [the] office and that was it.”

  A young Kristofferson, right, with fellow songwriter Vince Matthews.

  Courtesy of Tommy Wayne Burlett

  While he cleaned ashtrays, fetched coffees, and bulk-erased tapes, Kris witnessed the final three days of Dylan’s first foray into Nashville. In those days, writers affiliated with reputable publishing companies freely came and went in the middle of sessions around town, so Kris was no stranger to the scene at Columbia. However, Dylan’s scene was another sight. Off-duty police officers kept an eye on ambitious fans, while a strange silence enveloped Dylan himself. “He went in, started writing at the piano, and sat there all night long, working on stuff,” marvels Kris. “And around seven in the morning, he’d get all the guys in there—they’d been off playing pool and Ping-Pong—and he’d go in and cut some masterpiece. I was in awe.”

  A romantic telling of this story has the lauded poet mentoring the novice in some small way, but Kris never sought out such a moment. “I talked to his wife—his wife and kid were sitting in the control room. But I never would have talked to him because he was creating. He was out there writing. I couldn’t have brought myself to interrupt his thoughts.”

  In the weeks after Dylan disappeared, Kris slipped demo tapes of his songs to Johnny Cash, still as edgy as the night he first met him. But he doubted that the star ever played them. And he tried to revive his recording prospects, having Marijohn Wilkin produce his composition “The Golden Idol,” about a girl who wore too much makeup. But it tanked.

  Kris’s parents and siblings thought he had lost his mind, wasting his pedigree and impressive educational and military credentials on the songwriting life. His brother flew from California on a futile mission to snap him back to reality, and his father’s disappointment was plain. “[They thought] I’d gone down to shit-kicker country and they couldn’t imagine that there was anything worth devoting your life to here,” says Kristofferson. “I just thought, ‘Wow! They don’t understand.’ Well, looking back, I can understand why they felt that way! Because they didn’t even listen to the Opry.”

  Jack Clement remembers a letter from Kris’s mother arriving shortly after her son had settled into Nashville. “It was like a two-page, single-spaced letter. His mother was just really putting him down for what he’d done. She was telling him how irresponsible he was and all this shit. At one point, she said, ‘When you were thirteen years old and singing Hank Williams songs, we thought that was cute. But now I don’t think it’s cute at all.’ She ended it by saying, it doesn’t matter how much money or success he makes in the music business, it’ll never make up for what he’d doing now.”

  In comparison with the scene at home in Nashville, his parents’ dissatisfaction seemed insignificant. The songwriter’s late nights and all-hours job at the studio were splintering his marriage. Frances naturally had grown impatient with the uncertainty that replaced the respectable military career. Money was tight and concerns over the health of their newborn son excruciating. “He was born with his esophagus and trachea attached, a bad time,” recounted Kristofferson in 1974. “Ran up about a $10,000 hospital bill.” To pay the bill, he left Columbia and took a job transporting roughnecks by helicopter to oil rigs in the Gulf of Mexico. He rushed home to his music buddies on days off, and he never stopped writing.

  But Frances clung to the upper-middle-class ideals of her childhood in the face of Kris’s recklessness. His was the honky-tonk life, ambitious drinking mixed with impromptu jam sessions and casual romantic encounters. And in stark contrast to the image he cut when he married in 1961, he let his hair grow down to his ears and adopted the jeans and vests of his younger Nashville brethren. Often, he fell in with the veterans, like one night when Billy Ray Reynolds, Kris, and Waylon closed the Starlight Club on Dickerson Road.

  Seemingly out of options, the gang impulsively headed to Audrey Williams’s house. “It was about three o’clock in the morning,” says Reynolds, “and we knocked and she came to the door. By then, Audrey had lost a lot of weight and really wasn’t in good health. She said, ‘Honey, what are you doing out this time of night?’ I said, ‘We come to hear
some Hank Williams stories.’” And the next night Kris might step out with the newcomers, writers such as Mickey Newbury, Donnie Fritts, and Vince Matthews, who measured the pulse of the street for song ideas, and young musicians who pondered not the ghost of Hank Williams but the artistry of Bob Dylan.

  The people around Kris would soon help lift him to fame, but for now, he took pleasure in the thrill of his songs appearing as album filler or on a B side, like “No One’s Gonna Miss Me,” which showed up on a brand-new single by Waylon Jennings and Anita Carter in 1968. He gingerly carried it home. “I was trying to make some impression on my wife, who hated country music,” he explains. “I said, ‘Look at this. I’m making it.’ I was a janitor at the time, so she was pretty depressed. She played it for the people at her bridge club, and she said, ‘Well, they don’t really like his voice.’ And I just thought, ‘Well, we are never going to be on the same planet.’”

  While friction escalated in the family, Kristofferson also felt squeezed from time to time by Music Row rules that also stifled Waylon and Willie. Only it was Kristofferson’s songwriting that sat in the crosshairs. Music publishers demanded snappier scenarios and broadly appealing hooks, but his songs refused to fully conform, like “Best of All Possible Worlds” which again revealed Kristofferson’s education by recalling a line from Voltaire’s novel Candide. “They wouldn’t let me demo it the way I wrote it,” Kris told writer Peter Cooper. “I wrote it as, ‘If that’s against the law, tell me why I never saw a man locked in that jail of yours that wasn’t either black or poor as me.’ They wouldn’t let me say ‘black.’ I changed it to ‘low-down poor.’”

  I know a lot of times I’ve read that Newbury and I changed things here. We didn’t do it. It was them. It was John and Bob Dylan who changed Nashville from just being a country hick place to all of a sudden being something important that you ought to examine.

  —Kris Kristofferson

  Three

  * * *

  Let a Flower Be a Flower

  THE MUSICAL FREEDOM that Waylon, Willie, and Kris yearned for in the late 1960s seemed out of reach in the sterile new office buildings and sagging bungalows that housed the record business on Music Row. The corporate enclave ruled every country artist in town. Except for Johnny Cash, who under the cover of midnight darkness lugged his guitar and his band into the studios of Columbia Records.

  Cash followed his own rules in the studio, uncorking classic records that dealt with war, the plight of the American Indian, and other thorny topics—a departure from more traditional subjects of love and heartbreak. Cash’s producers let Cash be Cash, which meant throwing away the studio clock, leaving his backing band the Tennessee Three alone, however calcified its boom-chicka-boom rhythm had become, and standing by without complaint while Cash ploddingly chose songs and worked out arrangements—A&R tasks that elsewhere on Music Row would have been completed days before the session. When Waylon Jennings demanded and got such freedoms from RCA-Nashville in the early 1970s, many proclaimed that he was the first. In truth, as with so many things in that town, Cash—the godfather of Nashville’s outlaw movement—had gotten there first.

  Bob Dylan came second. He arrived in Music City on February 14, 1966, to record Blonde on Blonde and, like Cash, presided over sessions that were the antithesis of Nashville Sound. With the exception of multi-instrumentalist Charlie McCoy, who had traveled to New York in 1965 and unexpectedly played guitar on Dylan’s Highway 61 Revisited, none of the Nashville musicians on Blonde and Blonde had worked big-label sessions that were so free and easy. Throughout six days of recording, interrupted midway by a few live shows, Dylan wandered into Columbia in the evenings, spent hours scribbling down lyrics and a few more on music, then recorded in the morning. Songwriter Billy Swan was in the final days of the engineer’s assistant job that he would soon give to Kristofferson during those sessions. He admits that he had only haphazardly followed Dylan’s career up to that point, but in between his gofer tasks, he began to see the light. “What was coming back from those speakers was so fucking good: his singing, his performing. That whole album is fantastic.”

  LIKE DYLAN AND Cash, producers Jack Clement and Fred Foster modeled independence in Nashville. Fixtures in town by the mid-1960s, the two men still lived in the shadow of Owen Bradley and Chet Atkins. But not for long, as their wily hustle and passion for music for music’s sake created a thrilling alternative to corporate music making and would attract various freedom-hungry outlaws in the years to come.

  Clement stood out in Nashville like a juggler in a funeral parlor. He had established his producing credentials at Sun Records in Memphis, where he worked on Johnny Cash’s and Jerry Lee Lewis’s recordings. Plying an impulsive spirit that only Memphis could nurture, he dug feverishly through Nashville’s creative world as if it were an old attic chest, and pulled out the old and the unusual, but particularly the unusual. In the 1960s, he dusted off the career of long-forgotten country music father Ernest “Pop” Stoneman, wrote novelty songs for the grim Johnny Cash, and persuaded Chet Atkins to sign the black singer Charley Pride.

  “They all wanted to be around Jack,” says Jim Casey, who wrote for one of Clement’s publishing companies in the 1970s. “Jack would smoke a little dope and do crazy stuff and put them in a chair and spin them around and get them dizzy and play them crazy shit. They’d come to town and that would be the first place they’d go.” Toting his ukulele, he was always up for a good sing-along or a night on the town. Waylon’s drummer Richie Albright met him for the first time outside Sue Brewer’s Boar’s Nest: “I got out of the car and just as I was walking up the sidewalk, this guy comes down and I looked up and it was Jack. He walked down the stairs and stopped on the stoop, and I said, ‘Jack?’ He said, ‘Yeah.’ I said, ‘I’m Richie Albright.’ I put my hand out and started shaking hands, and he turned around and threw up. He hung on to my hand. So that was my introduction to Jack Clement.”

  Cowboy moved to Nashville in 1959 as a freelancer, performing various production chores for Chet Atkins and writing hits such as “Miller’s Cave” for Hank Snow and “I Know One” for Jim Reeves. An investment in a studio in Beaumont, Texas, pulled him out of town for a few years, but by 1965, he settled back in Nashville just in time to greet Kristofferson on his first day in town. In addition to producing Charley Pride and Pop Stoneman and the Stoneman Family, he supervised the recordings of the Glaser Brothers (Tompall, Chuck, and Jim), and in 1969 opened Jack Clement Recording Studios at 3102 Belmont Boulevard, a few blocks east of Hillsboro Village.

  The stars—Charley Pride and Johnny Cash—turned to him for ideas, but he also attracted writers such as Jerry Foster, Bill Rice, Vince Matthews, Bob McDill, and Townes Van Zandt, all of whom made deep impressions on Nashville in one way or another. “Jack had enough of that Memphis thing in him that he was willing to try anything,” observes Casey. “Nashville is very conservative. Nobody wanted to take many chances. Jack was willing to try things and that’s a Memphis thing.”

  It might also be a North Carolina thing. Fred Foster was born there in 1931, the same year Clement was born near Memphis. Like Clement, Foster came to Nashville looking for a poker game, arriving in 1960 and quickly revealing his preternatural knack for building winning hands with unlikely cards.

  Roy Orbison had floundered on Sun Records and RCA in the late 1950s before Foster signed him to Monument Records, which he had established in Baltimore in 1958. Orbison enjoyed his greatest days in Foster’s care, with hits such as “Only the Lonely (Know How I Feel),” “Crying,” and, of course, “Oh Pretty Woman.” When Orbison left Monument for MGM Records in 1965, Dolly Parton appeared to steal Foster’s gaze. Up to that point, the determined young woman from the Smoky Mountains had failed to break nationally, striking out on two labels. With Foster at the helm, her next two singles climbed the country charts in 1967—“Dumb Blonde” and “Something Fishy.” They spent a combined twenty-six weeks on the countdown and attracted Porter Wagoner, who promptly spirit
ed Dolly away to RCA and Chet Atkins.

  Fred Foster.

  Photograph by Alan Mayor

  If Foster had done nothing but cement Roy Orbison’s and Dolly Parton’s roads to the top, his legacy would be secure, but he had also spied an attractive hand in the black audience that big-label Nashville ignored and left to the tiny black-oriented record companies that dotted the city. Foster’s operation stood somewhere between the two: small enough to take risks and big enough to exploit black markets more successfully than the smaller outfits. “Monument had sort of become a pet of radio,” recalls Foster. “So I cut an R&B record and shipped it. The phones went wild! And telegrams poured in, letters from radio stations, criticizing me, ‘What are you trying to do? We put on a Monument record without auditioning it because it’s always good. Here we put on something and there’s screaming and hollering in the middle of our program—what in the hell are you doing?’ I said, ‘Well, I can’t do that anymore.’ So I started an R&B label.”

  Like Jack Clement, Foster also housed young writers under the shelter of his publishing company, in his case Combine Music, which he established concurrently with Monument in 1958. The company had given Dolly Parton a contract before she bolted to RCA, and throughout the 1960s attracted such artists as Ray Stevens, Chris Gantry, Billy Swan, Dennis Linde, all of whom wrote songs that bored into Nashville’s musicscape and enjoyed Foster’s sponsorship without interference. “You’ve got to let a flower be a flower,” declares Foster. “You’re going to make a flower bloom differently than it would normally bloom? I don’t think so. Just nourish it, give it enough fertilizer, water and let it bloom. It will bloom. Business, hell, I can’t stand it. Business has ruined many a good man and woman.”