MOMENTS OF FOREVER: Kris Kristofferson's Love for ALL Defines His Llife

Willie and Kris were playing the Miami Marine Stadium, basically covered bleachers on a small inlet that ran along Key Biscayne. It was a scrubby situation, designed for South Florida rednecks to watch speed boats race and take jumps, just metal bleachers with an overhang to keep their hangovers from baking them out of their mortal coil in the scorching Saturday high noon sun.

The stage set on pontoons. The backstage was a couple of low rent yachts.

When the call from the promoter came – “Would you like to interview Kris Kristofferson?” – I couldn’t say “Yes” fast enough. He seemed surprised. Kristofferson had become an actor and an activist, far more than a songwriter or rock star. I was the cred freelancer covering country, black and rock of a certain stripe.

How do you tell a middle-aged white guy you and one of your friends once cut out of school one afternoon, took two Rapid Transit trains to Van Aken Center to watch the afternoon showing of “A Star Is Born”? Explaining that his swagger, shirtless or in a poet’s blouse was dangerous, bravado forward, but poetically elegant would be moot. He was a pirate, a rock star, a gypsy and a man who took great risks, reached deeper into the human condition and offered up the pivot points of pain, dignity and courage without furrowing his brow.

Heck, my father started telling me about Kris Kristofferson when I was a kid, propped between my parents watching “The Johnny Cash Show.” Landed a helicopter on Cash’s lawn to give him a tape. Janis Joplin’s last hit – the one after she died – was a Kristofferson song. He understood addicts, alcoholics and washed out losers in a way that meant they weren’t actually born to lose.

Oh, and he’d gone to Oxford.

Yeah, I wanted to interview Kristofferson, whose music career was sagging, but whose mark on American songwriting was already indelible. Rushing to the morgue to pull the clip file, I blessed the Miami Herald’s Fred Burger, who’d covered so many of the Outlaws and other progressive country acts with a matching eloquence. He not only had several pieces, he’d seen to it that the artists he thought were important had clips from other sources in there as well.

Reading, reading, reading. Boxing, the Air Force, a Rhodes scholarship, William Blake, a teaching appointment, flying out to oil rigs in the Gulf of Mexico for extra money, parents hated the idea he would give up his legacy to write songs. Janitor at CBS Studios, where Bob Dylan was recording; dreamer who kept handing out demos, making friends with Willie, Cash, Waylon, Roger Miller, all the other travelers seeking to make a more elevated, sophisticated kind of lyricism with an even simpler melodic zone.

When the call came through, I was ready.

Scrawling my own kind of shorthand, the voice was ruddy, rich, warm, like a savory biscuit slathered in  something delicious, something like apple butter. He was laughing a bit, telling his stories, thinking about some of my questions, really honoring my curiosity. And that’s when I shot my shot.

“So what was it like, studying with William Blake?”
“Excuse me,” he said, tone twisting around itself a bit.

“William Blake, you studied with him…” pause, then adding helpfully, “at Oxford.”
“I’m sorry…” the voice on the other end was puzzled, then a giant laugh rolled down the phone.

“No, no, you studied with William Blake,” I protested. “It’s in the morgue.”
“Honey,” he said, tamping down his chuckle, “William Blake is DEAD.”
“I, uh, uhm,” the mortification was immediate. “Can you give me one second?”

“Sure, honey,” he graciously responded. “Take your time.”

Head down on the classical writer James Roos’ desk, I silent screamed like I was auditioning for a slasher film. And then I did it again, and again, and a fourth time. Exhaling, knowing I needed to pull it together because my 20 or 30 minutes was evaporating, I closed my eyes and reminded myself I might be 19, but I am a professional.

“I am so sorry,” I began picking up the phone. Kristofferson kept laughing. “I am so embarrassed. I was reading all the clips, and I swear, it was there… I didn’t just make it up.”
“Holly,” he said, cutting me off at the pass, “can I ask you a question?”
“Sure.” At this point, he could end the interview. It would’ve been deserved.

“When was the last time – do you think – someone asked me about William Blake?”
I was silent. I had no idea. I didn’t want to make it worse.

“You there?”

“Yes, I’m here.”
The voice was kind, not chiding. He obviously recognized how stupid I felt. It appeared he felt for me: a young writer at a good paper who made a gaffe of Olympic measure. “Holly, I’ll make this simple: no one ever asks me about William Blake. I’m not sure most of the journalists I speak with even realize I know classic English poetry.

“The fact you did? You get all kinds of points for that.”

We talked for another 30 minutes; far longer than was booked, so he could answer all my questions. The story was good enough, it made the cover of the Weekend section, I believe left well and above the fold; though it might’ve been the entire bottom third all the way across.

Before he hung up, he asked another question. “You coming to the show?,” which I was.

“Okay, then do me a favor. I’m going to leave you a couple passes. I want you to come back and say, ‘hi.’ Can you do that?”

“Uh, sure,” I said, knowing full well rock stars never remember. They don’t. Ever.

Until I got to the box office. Not only were the seats the first row that rose up so you could see over the four or five rows on the flat, but there were the two backstage passes. My second fiancee, twice my age and never one to come to shows, looked at me with a cockeyed grin.

“Well, Gleason, look at that. Passes! You must’ve made an impression.”
I’d not told Jason about making an ass of myself, played it off as the promoter being grateful. My fiancée, who loved Willie and Kris, said, “Well, you need to go back there, say ‘hello.’ I think it’s important. Those are really serious artists…”
“Are you going to come?” That might’ve been even more embarrassing.

“No, I’m not going to come. Some things in this world, you need to do on your own. You need to walk back there and be Holly Gleason, the writer from the Miami Herald.”

“Yeah, okay, I’ll think about it.”
I was definitely not going back there. Sitting quietly, wondering when the show – a good 15, 20 yards away from us – was going to start. John Valentino, the dark, lion-haired promoter rep, was suddenly squatting down by my seat. He was smiling. “Hey, somebody backstage wants to meet you. I’m supposed to bring you back to say ‘Hi.’”

“Gosh, it’s awful close to showtime.”
“Yeah, I don’t think the show’s starting ‘til you get back there.”
Slowly I rose, grabbed my purse and fell in behind the nicest man in South Florida concert promotion, who told me how much he loved my story. He remarked that everyone attached to the show really loved it, so he was glad they sent him out to get me.

“Yeah, yeah,” I said, clearly out of sorts. Pontoons on a choppy bay are no fun to walk on. Holding the ropes, feeling like my knees were buckling, I would lurch forward, hoping I didn’t fall straight into JV. When we finally climbed up on the stage, he took my hand, guided me around to the back and waved towards a gang plank down onto a boat. “Go ahead.”
Standing right where you’d step off, in a black tshirt and jeans, sinewy, slightly salt in his pepper and oozing charisma, Kris Kristofferson went, “Well, you must be Holly! And you look even younger than you sound.”

“I’m 19,” I said, used to people assuming a Herald writer must be in their 30s. “Hello…”
I put my hand out, he pulled into a hug. A big, friendly, warm and loving favorite uncle hug.

“That’s more like it,” he said. “And I wanna look you in the eye, and tell you that’s one damned fine piece of writing. I can’t believe you got all that from the scraps of conversation we had.”
He was smart: get me talking about the art of writing. Suddenly, we were writers, not a kid and an icon-in-the-making.  By leveling up, he made the awkward disappear.

“Are you kidding? Those answers were great. Your story’s amazing. And I got to write about all your songs, the way you use words. How could it not be great?” I asked.

“You’d be surprised,” he said a little too knowingly. I was young enough to not realize how cynical and crummy journalists could be once the white-hot moment had passed.
“I guess, but I still think if the songs are good, the conversation is excellent, the writing should lift itself.”
“You might think, but I promise: it doesn’t. You write like this at 19, I don’t know what you’re majoring in, but you should think about being a writer. You can write, and I know that’s not even what you’re studying.”
Holy crap! He remembered. He remembered me telling him my Dad wouldn’t let me study journalism or English, because I was a published writer from the time I was 14. Whoa.

The tour manager stuck his head over the side. “You ready?”
“I guess so,” he said. Then he looked at me. “Wanna watch from the side?”

“Hell yes,” I thought, but wanted to act cool. I said, “That would be nice.”
It was an open stage. I figured my boyfriend would see me. If he got mad and left, I’d figure out how to get home. Right now, I was going to stand a few feet away from Kris Kristofferson, so lean and cool, and watch him sing “Help Me Make It Through The Night,” “Sunday Morning Coming Down,” “The Silver Tongued Devil and I,” even “Jesus Was A Capricorn.”

Tasting the salt in the air, a tropical breeze blew across the stage and pushed his shaggy hair off his face. He really was beautiful, even more beautiful than in the movies. But his passion when he sang those songs, the vulnerability and willingness to show the broken places was mind-blowing. And talking about going to church with a lady named Connie Smith, walking to the altar and falling to his knees inspiring “Why Me, Lord?,” it opened a portal into blessings where it's all falling apart.

He and the band tromped offstage. They swept me up with them, then Kristofferson cut me from the pack. “C’mon,” he said, and walked me over to the other boat.

“Willie, this is the writer I was telling you about.”
Nelson was sitting with the writer from the Fort Lauderdale Sun Sentinel. He smiled and nodded. “Come sit,” he said. “Visit for a few minutes.”
Kristofferson bounced off the boat, probably to towel off from the swelter. Willie Nelson, his braids shorn into a flat top, looked exactly like my grandfather who’d just died. I was dumb struck, literally unable to speak.
“That was a fine piece you wrote,” he said. “Kris said he thought you were young. I don’t think anyone thought you were…”
“This young?” I managed. “Weird, ‘cause we talked about school.”
“Sometimes the details don’t register.”
“I get that.”
“It’s really about the work.”
“I get that, too.” Never have I struggled so hard to stay in a conversation.

When the promoter came to take us away, he was buoyant. “I am so proud of you,” JV said. “I am so proud you wrote a piece that made them want to meet you.”
“Yeah, wow,” was all I could say.
My boyfriend was so impressed. He actually told me, “If Willie would’ve let you stand on the side of the stage, you should’ve…”
“No, they definitely showed me out.”
Clang! Clang! Clang! “Whiskey River” kicked into gear, bottles – and a few drunks – started raining into the water between seats and stage. It was raucous. Lots of bikers, as well as kickers and redbecks. They came to dance, throw down and get lit.

By the time Kristofferson returned to the stage for a bawdy “How Do You Feel About Fooling Around” and “Circle Be Unbroken,” the place was unraveling. This was the power of unadorned music thrown to the crowd like gold coins and roses; people scrambled to grab what they could of the moment, to pull those emotions towards them.

Imagining this must’ve been what the Allmans were like in their prime, I held the back of the seat in front of me, a little dizzy. One man had a hand in getting President Carter elected, the other made landmark films like “Alice Doesn’t Live Here Anymore.” Both of them had talked to me; I would be in a daze for days.

“Here Comes That Rainbow Again,” to drop one song in among all the others, speaks so much to the way those men saw the world. Set in a café, dust bowl nowhere kind of town, a waitress took mercy on two hungry-eyed kids, telling them the candy they coveted was two-for-a-penny; it was exactly the money the children had.

A truck driver asks the waitress about why she did it. She asks, “What’s it to you?” believing in kindness over the straight bottom line. To her surprise, when the two truckers leave, there’s a small windfall at the table. Chastened by her kindness, they raised her ante and left a tip to say that kindness is the way.
An O. Henry short story over a classic folkie kind of melody, Kristofferson suggested what doesn’t kill you is worth indulging if it gives someone a little magic or breaks their melancholy. In the brightness and innocence that washed away the cynicism and world weary, the Songwriters Hall of Famer who received their Johnny Mercer Prize transformed anyone who listened.

When The Highwaymen, produced by Chips Moman, turned Waylon, Willie, Kris and Cash into the first true supergroup, the buzz was deafening. Tower Records’ PULSE assigned a cover story to me; all I had to do was juggle classes, superstar availabilities and not choke. At the time, this was the Mount Rushmore of the genre, and I understood even more now than when I’d done the Marine Stadium preview three semesters before.

First thing out of Kristofferson’s mouth, even before “Hello,” was “I just want to alert you: William Blake is still dead!” He laughed. I laughed, It was a riff on a “Saturday Night Live” bit, but it was also a small private joke, shared between the star and the humble scribe.

From being a total dodo to having a private joke? That was what made Kristofferson so lovely. He wanted to take the beat-up kid, find a way to usher her into the club. He wanted to connect some of the dots on the songs; they had Woody Guthrie and Cindy Walker, Ed Bruce’s “The Last Cowboy Song,” Guy Clark and Jimmy Webb, Bob Seger, two Johnny Cash classics, a Steve Goodman/John Prine co-write. We talked songwriters like people swap baseball cards; he spoke of what was inside the ten selections that made the album
It was strength without bullying, manly, not machismo. There were themes of social conscience, of passing time and tough places. These weren’t party songs, but things to make you think about the state of the world, how people treat other, who we throw away. It was smart and sobering as a work, and rich in terms of what we talked about.

He thanked me when he hung up, told me it was always a pleasure. I thought, that’s because you’re so good to talk to. Anyone not enjoying talking to you? They’re not doing it right.

Of course, Kristofferson was getting ready to get back into the water as an artist. He had a film with Nelson called “Songwriter,” a madcap sticking it to the Boss Hog music industry guy that looked like fun to make – and gave you a sense of how Nashville was when the creatives really were their own class of people. Independent, figuring out how to work between the lines, ready to hit the road, willing to go to any length for a practical joke and looking for a hit without selling out.

But Repossessed, a decidedly political album of social reckoning, was coming. It pulled no punches, threw down and drew lines. “Mean Old Man” and “Anthem ‘84” set the tone for a cruel, consumed by consumerism world and “They Killed Him” called out a culture that killed its visionary leaders, slaying them to never have to consider the truths Ghandi, Martin Luther King and the Kennedys put forward.

It was bold, and it struck a nerve if you listened. Most people chose to tune the radicalism out, marginalize the movie star who’d not had a hit album in a long time. When the phone rang at my desk at the Palm Beach Post, Kristofferson asked me what I thought. I told him I had hippie babysitters, this stuff is critical – if we can’t come together in peace, we would perish in the divisiveness.

With a band that had Billy Swan and Donnie Fritts, there was plenty of funky grit to go around. An outdoor show, it was a motley audience who showed up. Women swooning, because he was so fine. Vets and bikers who respected his courage for speaking up. Some country music fans who believed in the catalogue of many of their favorite artists. Native Americans who honored the way Kristofferson spoke to and for their heritage.

A melange of humanity, coming together in the songs. We didn’t speak that day. No backstage passes, though I was sure he saw me in the crowd, winked and nodded. That was plenty. Why crowd a legend when you can interview them for the paper?

By 1990, the politics had sharpened. Songs like “Jesse Jackson,” “Third World Warrior” and “Sandinista” left little to the imagination. He didn’t care; wasn’t going to pull his punches. He’d rather make music he believed in, cut live in the studio with his guys, that spoke the truth no one wanted to discuss. He wasn’t desperate, but was raging against a machine that wanted to use pop culture to distract America from what really mattered.

Like Jackson Browne, he spent his time talking to thinkers, leaders, the people on the front lines. He used his platforms – he was still an in-demand actor – to spread what he knew, and he knew plenty. He put his career and his life into the causes he believed in. And he just kept coming.

Somewhere in all of that, he fell in love with an ashy blond who was as fresh-faced and smart as they came. He and Lisa built a life, a family, kids who went in varied directions, saw the world and raised people’s consciousness. Mostly, they were love in action – and they served as an example of what can be if you truly commit and support another human being.

Just the way he looked at Lisa and smiled, you understood why he was the thinking woman’s heart-throb. That is how every woman deserves to be seen, but also respected.

He may’ve been an international superstar, touring the world with the Highwaymen or making any number of films. But mostly, he was a family man and the lover of Lisa. That was his joy, his grounding. In Hawaii, where they moved, all the local children adored him, too, called him Papa Kris – and followed him around, laughing and loving him as their own.

He stood up for the underdog, the little guy, the bullied and the overlooked. When Sinead O’Connor appeared at the all-star Bob Dylan Tribute Concert, held at Madison Square Garden, the air was charged. She had recently torn up a picture of the Pope on “Saturday Night Live,” igniting death threats, boycotts and being denounced by every Catholic organization in the world.

Brave, she took the stage, eyes piercing and seeking. She had come to sing for arguably the greatest songwriter who’d ever lived. Before she could get the first note out, an avalanche of boos hit that stage like a mountain collapse. Unable to withstand the velocity, the Irish songwriter/vocalist collapsed into a cloud of tears — and Kris ran from the wings to shepherd her off, cloaked in his arms.

As soon as he reached the shuddering musician, she proceeded to vomit. The vitrol she’d absorbed had to go somewhere. Kristofferson held her for a moment, assuring her the artists were with her; offering strength and comfort in a dark place, a pummeling moment.

If he didn’t suffer fools, he was generous with his praise. When an Oxford American think piece for his meditation on aging Feeling Mortal crossed the family’s horizon, he marveled that “Holly wrote that?,” no doubt picturing the kid from decades prior. When he saw me, he laughed and told me I’d clearly grown up.

And when “Better As A Memory,” a two-week No. 1, received it’s BMI Award for Most Played Songs of 2008, it was chaos as I teetered up to the stage in my 5” stiletto ballet slippers.

“Can you walk in those things?” BMI Nashville head Jody Williams inquired. “If you can, close your eyes and open them when I say…”
Like a good dancer, his hand slipped to the small of my back. Turning me 80 degrees, I heard now, and opened my eye lids to see Kris with his fingers in his mouth leading a standing ovation with Don Was. Surreal doesn’t begin to cover it, but my feet hurt, my heart was in my throat and tears were in my eyes.

“Can you believe it?” Jody asked. I shook my head no, because, well, it was hard to take in.

Pictures taken, someone escorted me off the stage. Before I could make my way across the room to say “thank you,” they were gone. The CMA Awards were the next day, so most likely they had an early call for rehearsal, or meeting because they were actually in town.

Walking out of our own rehearsal, I was talking to Clint Higham, Kenny Chesney’s longtime manager, about how the runthrough had gone. Coming in and cutting against the grain of rushing talent support teams, Kris was making his way towards us.

“I was so proud of you last night,” he said, taking my hands and looking into my eyes. “That is a damned fine song, Holly. A damned fine song, and you wrote it.”
I just looked at him. Cry? Laugh? Whoop? Busting a smile that was as wide as my face, I said “Thank you, and thank you. When I saw you and Don, I almost lost it.”
“We almost lost it, too,” he said. “Lisa had to tell me it was you…”
“Because you’ve never seen me in a dress.”
“Yes,” he admitted, laughing.

“Well, now you have.”
The talent wrangler came and got him, but we hugged. He told me I’d done good as he walked away, and I felt a little bit taller. If people had scoffed about me writing a song, they forgot I did it under another name so the song could have a life… and it did. If people acted like anyone could do it, like it was my proximity to Kenny that got the song cut, I didn’t care in that moment. Kris Kristofferson told me I’d written a damned fine song.

And when Kenny Chesney went on to co-produce Willie Nelson’s A Moment of Forever with Buddy Cannon, that Kristofferson title track wrecked me. A quiet performance, contemplative, yearning and yet thrilled with what has been shared, Kristofferson’s song was about the hope and wonder that even a transitory connection can yield. It’s not what was lost, it was what was felt.

Listening to Nelson in the studio, a witness to so much living, loss and adventure, the song felt like the wisdom of time. It also felt like a leavening exhale in a realm of shrinking connections, devastation and people lost not to fights or other lovers, but leaving this world.

When Kris began to fade several years ago, a bad diagnosis that Lisa refused to accept, they both hung in, seeking answers that would refute the diagnosis. One came, Lyme disease, and health returned, though the fragility of aging crept up in small degrees.

Still, there was Kris out playing with Merle Haggard’s kids, showing up at Farm Aid, being honored on the Outlaw Country Cruise. There was a tribute album. There was picking up Jerry Lee Lewis’ Country Music Hall of Fame medallion and delivering it to the Killer in Memphis.

Always something, always love.

Always love.

The last time I saw Kris, it was from eighteen rows back at the Hollywood. Rosanne Cash, beaming, walked across the stage as her rich, coppery alto followed the gorgeous imagery upwards. “Loving Her Was Easier (Than Anything I’ll Ever Do Again)” may be Kristofferson’s most gorgeous song, and Cash grew up knowing poet laureate of the Outlaw movement long before she was herself a formidable songwriter and artist in her own right.

As the first verse  concluded, she reached her arm to the wings – and Kristofferson, eyes the purest blue of early morning, walked towards her in a parsons coat. Hair white, but flowing over his collar, he beamed right back at her, clearly knowing this was a moment to transcend all of our mortal realities. Rosanne continued to sing, Kris leaned into her and the mic, found his way.
They tangled voices, words, emotions on a song about letting go of someone you loved so they can find something better. Triumph in the sadness, a light that shines from doing the right thing. They both sang from a place of intimacy, a knowing that few can share. Though they had never been lovers, they had been life companions since Rosanne was still a girl – and when he looked into her eyes, you could see the pride he felt for the woman she’d become.
“Dreaming is as easy as believing it was never gonna end…” the song extols. Looking at the legend, Rosanne almost melted with her heart on her sleeve. Kris was savoring all that was, looking at her in pure delight. It was perfect, so perfect Cash dropped out, and let Kris have that final “do again…,” collapsing into his arms in an embrace that spoke to how precious their connection remains.

Turning away from my editor at POLLSTAR, I could feel the tears on my skin. Here was a man who’d seen so much, who should be eternal and always. Here was a man who wrote about hangovers (“Sunday Morning Coming Down”), needing human congress to survive the ache of living (“Help Me Make It Through The Night”), who knew that even when it’s over there’s a place for one last time (“For The Good Times”) and who understood the life-saving grace of surrender (“Why Me Lord”).
He was robust, tender, willing to let go. He spoke to the ‘70s zeitgeist when he wrote, “Freedom’s just another word for nothing left to lose…” on “Me & Bobbie McGee.” There was no room for anything but being wholly present, leading with love and standing on the convictions of right and wrong.

For all that he was, he was a distiller of hearts. He offered generations of people seeking to understand a better way to express their longing, frustration and truth. He was fearless, joyous and willing – and as he wrote, “Don’t Let The Bastards Get You Down.”
I promise I won’t. But I can’t say that I won’t cry all night. I can’t say that I won’t stare into space on a plane to the West Coast tomorrow, wondering about losing another beacon of light to the stars above. Too many precious ones are leaving, and I imagine them all sitting around a poker table, laughing and raising the stakes: John Prine, whom he helped launch, and Steve Goodman, Cowboy Jack Clement, his dear Johnny Cash, Ray Price, Sammi Smith, Bobbie Nelson, Waylon, Donnie Fritts, known to all as “the leaning man from Alabam” and so many more rogues, characters and dreamers.

It was inevitable, of course. People age, people fade. But the ones who write such truth, they seem as if they’re immortal.
After suggesting that you were young enough to dream, and I was old enough to learn something new, Kristofferson summed up the seekers condition adroitly. With a demi-chorus, he explained,

“And come whatever happens now
Ain't it nice to know that dreams still come true
I'm so glad that I was close to you
For a moment of forever”

www.hollygleason.com

BEYOND THE CORAL REEFER: Jimmy Buffett Finds That One Particular Harbor

BEYOND THE CORAL REEFER: Jimmy Buffett Sails Into That One Most Particular Harbor

It was always the ne’er-do-well golf pros. Everything cool, somehow contraband and just beyond the true reach of a 12-, 13-year old girl who was too thin and absolutely curious about what the grown-ups didn’t see because they weren’t paying attention.

Songs about smugglers, washed out drifters, deadbeats and writers would drift from that backroom, occasionally with a waft of steel guitar and some short blasts of harmonica. The voice felt just like one of those naughty golf pros – warm, familiar, welcoming, wry – except it had some flannel to it, some molasses and a bit of cayenne as it flowed over notes that lifted and fell like the curtains on a slow, humid night.

He sang of a Florida I knew from going to Pompano, Delray, Palm Beach to work on my golf game during the six, seven months Cleveland wasn’t hospitable to that sort of thing. When his voice drifted out the bag room on a small gust of gasoline, dope smoke and sweat, my ears pricked up for the stories, always the short stories about pirates looking at 40, men going to Paris to seek something, lives intersecting in Montana...on Monday.

It was all so romantic. Even before I knew about “Margaritaville,” because I lived in a place and time before that Key West loser’s lament became the freak flag, good-time National Anthem. Somewhere in the delta between personal responsibility and screw it, that song plumbed the awareness of a man who knew better, but just didn’t care.

Jimmy Buffett must have been changing labels. I bought all those ABC/Dunhill Records – it seemed – remaindered at Record Theater at the Golden Gate Mall. A1A after the single lane coastal road that ran along the east coast of Florida; the sunk skiff Livin’ & Dyin’ in Three Quarter Time that was too hillbilly on first listen, but “West Nashville Grand Ballroom Gown” reminded me of too many babysitters; White Sport Coat & A Pink Crustacean who’s “Grapefruit Juicy Fruit” felt like something I was living, a Gatsby world for a barely teenage Catholic driving to another golf tournament, as well as the slinky “They Don’t Dance Like Carmen No More” that saw my father wax rhapsodic about Carmen Miranda and then wince when “Why Don’t We Get Drunk & Screw” rolled up.

We didn’t think about “labels” then, just “cool” or “lame.” Cool, of course, came in degrees. Buffett was that uncle your parents wouldn’t let babysit, even if he could talk to them about sailing, literature or Gulf Coast resorts. That made his sangfroid that much more delicious to a kid sitting on a worktable in a back room, not getting all the references.

“Margaritaville” wasn’t a hit when people started singing it, just the self-confession of the guy who drank himself out of the deal – and wasn’t 100% sure he cared as the hangover throbbed. He was coping, tequila, ice, lime and blender. For a washout, it was perfect.

All the sun slaves loved it. Work hard, party hard, recover while you you’re onto the next.

I loved that he painted this Florida of black top turned grey by the sun, the old people in plastic shoes, Walgreens and crusty ne’er do wells in bar rooms watching the ceiling fans turn. He got the Key West of Hemingway, who I already adored, Tennesseee Williams, who would beguile me in college, as well as the next wave macho literary and creative brios Jim Harrison, Tom McGuane, Guy de le Valdene.

Key West was for pirates. Dusty, dirty, chickens roaming the streets, space between buildings that held Lord knows. It felt like electric creativity when my father and I would escape from “practice,” head South over the 7 Mile Bridge and set to walking the streets like the tourists we were: an older Dad and a scrawny little tomboy, both sponges for whatever was in the air.

He’d lie to Mom about where we were, that’s how I knew it was good. And when Buffett’s songs came pouring out of a muscle car’s rolled down window or in that badly-ventilated back room, I was right there at Sloppy Joe’s on a barstool next to my father.
“This is the stuff, pro,” he’d tell me. “THIS is... the stuff.”

Buffett was snide about the right stuff, tender with the good stuff and savoring of the naughty stuff. Even before he turned into a billionaire industrial conglomerate of frozen drink machines and retirement communities, he understood not just what mattered, but how.

If the Eagles were “The Dirty Dozen,” Buffett was Butch Cassidy’s “Sundance Kid.” He had the escape route planned; he wasn’t backing down and he wasn’t afraid to hit the tricky spot. At a time when Southern California rock included Jackson Browne, Linda Ronstadt, Warren Zevon, J.D. Souther, America, Neil Young to some, Poco to others, Buffett was the Southern cousin, a bit more leaning to the folkie side of singer/songwriter.

He ran with Jerry Jeff Walker, Jesse Winchester, Steve Goodman. He got those traditions. He exhumed Lord Tom Buckley’s “God’s Own Drunk (& A Holy Man),” which he delivered with a hilarious ramble on You Had To Be There. It was that notion of street musicians, playing for tips and vibes; a secret handshake and a wink to a counterculture that was as romantic as it was pungent.

“People ask me, where in the hell is Margaritaville?” Buffett says on You Had To Be There, after referencing the possibility it’s a little island in your mind or the bottom of a tequila bottle. Then he proclaims, “It’s anywhere you want it to be, baby...”

Postcards from a life I didn’t have agency over. Yet. People I didn’t know. Yet.
But I leaned into the poetry, loving the notion of captains and kids, characters painted with same detail John Prine conjured. But where Prine could be profoundly sad or lonely or conscience-tugging, Buffett was more the brio of the literati he was running with.

Dreaming dreams inside the songs has a strange centrifugal force. Like so many people who drift into the world not quite sure where they’re headed, it can pull things you never intended to you. Alex Bevan, my first folk singing idol who befriended a wet behind the ears kid, knew him from their days playing National Association of Campus Activities showcases, trying to get regional college dates. He’d talk of their intersecting wages of the road: afternoons in laundromats, talking about Goodman, Jerry Jeff and whatever.

Buffett hadn’t blown up yet. Bevan made him seem real-sized in a way. Even sneaking into “FM,” a film about free-form, big business rock radio, with cameos from Buffett and Ronstadt, the notion of pirating someone’s concert for broadcast seemed delightfully on point. In “Urban Cowboy,” he took that out West cowboy nonsense and lacquered dancefloor country with his zesty “Livingston Saturday Night,” no doubt informed by his writer friends who fled Key West for Montana.

And then I fell out of the sky at St. Andrews School in Boca Raton, seeking to be recruited for college as a golfer. It was a co-ed school with very rich kids who were sophisticated in far more fast-track way than Ohio. That was where I met Valerie.

Valerie de la Valdene, heart shaped face, tilted smile and a wash of ebony hair falling across her eye, was the daughter of a count. She was also Buffett’s godchild, and like me, a young’un used to running with older kids; she couldn’t drive, but she was one of us. If Eloise had been raised by adventure hunters, she’d’ve been Valerie, who ran up and down Worth Avenue barefoot, laughing madly and plotting the next adventure.

Valerie, who got us the tickets to Buffett’s annual Christmas show at Sunrise Musical Theater in Ft Lauderdale, who said, “You should review this for the Bagpiper,” our school paper. Being such a big Florida icon – even then –it seemed to be the most perfect idea. Until they used that issue of the paper for the annual fundraising drive, missimg my smirking reference to “Why Don’t We Get Drunk (& Screw)?”
What would Jimmy Buffett do? It became my sextant and compass. Looking at the Dean, who was braced for some kind of antics, I exhaled slowly, smiled innocently, and said, “Obviously these people are not music lovers...”

Jack Bower could barely contain the laughter. His face turned red; the howl was trapped in his throat. A theatrical man, husky but not fat, his eyes danced as he looked at me, suggesting I keep talking without saying a word.

“Dean Bower, that IS the name of the song, and it was a climax to the show. It was bawdy and brazen, but also self-deprecating and self-impaling. To not say it happened would be to not tell the story properly.”

He couldn’t take the mealymouthed sweetness. I was not that kid. He knew it. Barking as a laugh and his voice escaped, he managed, “Get out of my office. And please, Holly, be smarter please. The donors are important... They’re paying the bills.”

Turning in the doorway, I tried one Hail Mary pass. “Would it help if you knew I went with Valerie?”

I smiled. He laughed harder. It was implicit: while Buffett was the dope smugglers’ personal hero, he was also a saint in South Florida. Though his manatee awareness campaign was a few years off, he quietly did much for the region that was over-run by Haitian refugees, other Spanish speakers, profiteers who’d pave the Everglades and other entities to check.

“Get out, stay out of trouble. You know what to do.”

Yes, whatever Jimmy Buffett might do.

Still, he was quicksilver. Sightings all over the state. “Don Kirshner’s Rock Concert.” Concerts at Blossom Music Center, Sunrise, Rolling Stone magazine, softball games against publications and radio stations. It was a different time, and place.

One day during college, while clerking at the Miami Herald, a call came through to the general features desk. “HELLohhhhh,” the voice came down the line, “How are you today?”

No one was ever friendly on that extension. The euphoria felt real, the voice familiar.

“I was wondering if you could help me... I am trying to figure out where to get some good Thai food down here in Dade County. Can you help me?”
“Well, sir, uhm, we really don’t provi...” I was trying to avoid making a Herald endorsement.

“Honey, would it help if I introduced myself? This is Jimmy Buffett, and if the restaurant sucks, I promise we won’t get you fired.”

I turned purple. Of course, he won’t. He gets the plight of the late teenager/early twenty-something. I gulped; didn’t want him to think I’m stupid.

Putting him on hold, I asked a couple of the folks on the desk that I trusted. Got back on the phone, trying to “sound” like a pro, I picked up, “Okay, not sure where you are in the county, but the place you want is called Tiger Tiger... It’s down Dixie, south of the Gables, and it’s delicious. I think you’ll like it.”

“Awesome, baby. And if you can get out of there, you’re welcome to join us.”

He laughed and was gone. Dixie Highway is an easy navigation, especially in the ‘80s. Just get to Coral Gables and start looking; that restaurant was dark wood. It’d be easy to spot.

Whether it was a pleasantry or a genuine invitation, I was too intimidated to show up. Besides, real life drive-bys are only magic when you’re not stalking.

A year later, I would get to interview Dan Fogelberg, playing the NAMM Convention in Hollywood, Florida. He had a bluegrass album, High Country Snows, coming, and I stalked my story with a vengeance. It’s hard to say no to a kid with shiny straight hair in a striped t-shirt with hope in their eyes; the tour manager agreed, saying I needed to chase their limo to Ft. Lauderdale – and I could meet him in the restaurant, talking while he had his dinner. Nina Avrimades, his manager, was there; I tried to not be too excited, but I knew her name from Buffett’s record covers.

The Fogelberg interview went impossibly well. Turned out he’d had his dinner sent to his room; he was only going to have soup with me. But he ended up staying for the entire hour. When he left to go change, I set upon the lovely blond-haired woman, asking questions about what she did, how she did it.

“You know, he normally hates these things,” she confided. “Dan genuinely enjoyed that.”

Screwing up my courage, I asked the big ask.
I opened with the obvious, “You know Jimmy’s the Grand Kahuna down here. No one is bigger.”

She laughed. She saw the set-up, and she knew he wasn’t “in record cycle” or “touring.” We left it that she’d think about it, see what she could do. A couple months later, Buffett called my dorm room – and the Herald ran the piece.

So did Country Song Round Up, the world’s oldest country fanzine. My canny editor there told me about Buffett’s connections to Nashville, the reporting for Billboard magazine, the days hanging out at the Exit/In, Closed Quarters and the general creative hauntings. Suddenly, the Jerry Jeff Walker stuff, the steel guitars and the actual country undertow made sense.

It opened my mind to how impossible things can merge and converge; made Willie Nelson not the only one who could tap authenticity in seemingly opposing realms of music. But where Nelson was truly making country safe for the alternos, Buffett was slyly interjecting country music into songs people loved and never letting them realize it was “liver.”

It always seemed to be that way with this Buffett character. He existed in our world like twinkle lights in a bar; look up and smile at the twinkle in whatever other clutter was around. He knew poetry, knew how to deliver it – and he knew how to revel like an Endymion Mardi Gras float, tossing ravers out to the fans like so many fistfuls of beads.

Signed by Tony Brown, it wasn’t that Buffett came full circle, so much as music had turned all the way around to where the kid born in Pascagoula, Mississippi and raised in Alabama started his journey. Sure, there’d been Lear jets, misadventures, crazy stories, mysterious substances, inside jokes, sports teams and “60 Minutes,” but there was more to come. Writing his own books about Joe Merchant and memoirs, launching a chain of cheeseburger restaurants that turned into hotels, Broadway shows, football stadiums, creating a space for the regular guy to get a little tropicrazy and have the license to let your freak flag fly high.

All that was ahead of him. Records were a place to give his creativity a home. He was still everybody’s favorite “oh, yeah” songwriter/singer/supernova, but the Parrothead ubiquity was just starting to quicken. “One Particular Harbor” from that era was beautiful, a lulling melody that spoke of refuge and peace/piece of mind. It wasn’t what country radio was doing, but the video – possibly shot in Polynesia – was close to four minutes of mental escape every time it rolled up on CMT or TNN.
That escape was everything. As MTV blared and pulsated, Buffett was saner, smarter rebellion against 9-to-5 and the status quo. His touring business grew more robust without radio; his legendary Coral Reefers became more formidable. At different times, Timothy B. Schmitt (the ether-high vocalist with the Eagles), Josh Leo, Tim Krekel, Will Kimbrough, especially the tenderest hearted songwriter/guitarist/ Mac MacAnally, all artists in their own right.

Suddenly, it wasn’t about chasing hits, but the longevity of classic tracks, the opportunity to convene with your Parrotheaded brethren, to sing these songs together. Buffett was the grandmaster – and he took his duties seriously.

He used that power to launch Margaritaville Records, where he signed original Nashville compatriot Marshall Chapman for her It’s About Time: Live from the Tennessee State Women’s Prison project and a neophyte trickster/writer acolyte of Jerry Jeff and Keith Sykes named Todd Snider, whose mostly talking blues “Alright Guy” caused an alternative/triple a sensation.

Snider, a free spirit, and Chapman, a lanky rock guitarist with blazing charisma and a drawl for days, embodied that notion of outside the lines is the only place to color. Original voices and perspectives, they brought it with a burning intensity as different as the other – and as contrasting to Buffett’s cool

Chapman, opening for Buffett at the Hollywood Bowl, knew how to bring a Chrissie Hynde panache to a bare bones rock’n’soul grooved attack. She and her Love Slaves left those fans panting for more, and when the main dish is Buffett, that’s saying something.

Saying not just how astute a judge of talent he was, but his willingness to share the stage with a woman known as “the female Mick Jagger” in the ‘70s and the sly Snider, a songwriter who loved to see what would happen, including wandering off from the venue on one tour and not look back. That is all part of the carnival, the glorious feast Auntie Mame promised in the original Broadway show. If it gets twisted, that’s part of it.

So Buffett became an icon, larger than life – and somehow still inviting. A Saturday morning superhero, he was the kind of cartoon who was so frisky his skin almost seemed not enough to hold him. The tales of shots fired at his plane over Jamaica; the tales of adventures that inspired William McKeen’s Mile Marker 0; the charities he anchored and advocated for in New Orleans, the Hamptons, Mississippi, Alabama and Florida.

But even then, it was the random Buffett, the sightings of the man in the wild. Running into him in a purple label Ralph Lauren tux, where he got up and sang some for the wedding of one of his friend’s sons in Palm Beach; laughing jocularly at a CMA Awards after-party after singing “5 O’Clock Somewhere” with Alan Jackson; on his bicycle on County Road in Palm Beach, dropping by to see friends at PB Boys Club or reports that he was out surfing with friends.

Of course, he was. For while his brand was the guy who lived his life on his terms – St. Barths, St Kitts, Fenway Park, Wrigley Field, Jimmy Buffett actually inhabited a devil-may-care world where he just was. Not rejecting the fanfare, but laughing it off as he went.

Which isn’t to say he ever stopped thinking about what his next creative step might be. A million years ago, reading the Sunday New York Times and Saturday Wall Street Journal at the pool at a fancy Vegas hotel, he spent a little time with an emerging country artist, sharing some wisdom, talking about football and demonstrating how little one needed to change. That lesson served Kenny Chesney well; he remains indifferent to fame, investing his heart in the buzzy byproducts of making people happy with glorious concerts that remind them the joy of being alive.

When he played the annual Everglades Benefit in Palm Beach County, usually with some splashy single name guest, the high dollar tickets flew out. When the Gulf Coast was destroyed by weather, he got a few of his famous friends – and came in to raise millions of dollars. Big shows with an undertow of fun within the wreckage, offering hope as it solved or helped with problems that were critical.

If Springsteen wrote “It ain’t no sin to be glad you’re alive,” Buffett lived it. Top-to-bottom, front-to-back, inside-out and upside-down. It was a tilt-a-whirl, centrifugal force of ebullience – and it never flagged. Whether Las Vegas, peaking out from the wings, or West Palm Beach’s “what name is it this year?” amphitheater in the swelter, it always delivered exuberance and delight. If you came with a squad or a date, we are all one once the singers slithered onstage, the tin drums started their rolls and the churn started turning.

In 2018, fresh from induction into the SOURCE Hall of Fame, which recognizes women in the music industry behind the scenes, I boarded a plane to fly across the sea. All alone, my destination was Paris, France. To mark the triumph of the unseen, it didn’t matter that no one else could join me.

Raised on the poetry within songs, hearing Jimmy Buffett sing “He Went To Paris” at La Cigale seemed the most perfect way to hold that young girl who didn’t quite understand all the grownup emotions, but recognized the power in those songs. Deceptively engaging, Buffett – like the Texas songwriters, the wild authors and filmmakers of Key West – knew that if there wasn’t conflict or a yearning, the song didn’t lance whatever was stuck in the listener’s heart.
It wasn’t that I was numb from the music business, but it extracts a toll on women who don’t fly by their looks or native charms. I needed to remember those moments when a song sounded like something I could – and must – touch, and my heart sped up at the way the images often stacked up to create some truth about living.

Paris, as Audrey Hepburn declared, is always a good idea. The streets alive with passion for life, the different size glasses of wine you can order, the fabulous cafes, the bookstores, walking along the Seine, over the ancient bridges, the Deux Magots and Café des Flores, as well as the D’Orsay, Marmottan. Picasso Museum and yes, the teeny Hemingway Bar at the Ritz.

Stopping at Le Roc, supposedly the oldest Catholic church in Paris, I knelt in a chilly stone cathedral and wept for all that life had given me. So many blessings, adventures, wonders, people and dreams that came true; not just my own dreams, but the dreams I’d midwifed for artists who didn’t always see what I dreamt for them... artists who didn’t always see how their music changed lives.

Sitting so close to the stage later that night, taking notes to always remember, I was overwhelmed by how much joy could be delivered; also, the heroism washed out characters could have being true to their own shattered lives. “He Went To Paris” was, indeed, the miracle I believed it would be.

“Looking to answers... for questions that bothered him so...”
La Cigale, there in the 18th arronddisement, had quite the history. Built in 1894, Mistinguett and Maurice Chevalier had played there, later Jean Cocteau would stage avant garde evenings. It would become a movie theater in 1940, ultimately falling into a screening house for Kung Fu, then X rated films, but always it remained. Deemed a historic building in the 1980s, the French recognized its intrinsic essence – and Philippe Stark was drafted to return it to its former glory.

The metaphor was not lost on me, or the fact this less than 1000 seat venue was where Buffett chose to play. Like Key West in the ‘70s, it was the fabulous dissolute chic without resources that deliver dignity and delight right where you are.

I had traveled alone, but I sat in that row at La Cigale with every me I’d ever been. The little girl run off with the naughty golf pros, the baby rock critic people didn’t take seriously until they saw my words, the young dreamer working in a world where a journalist’s stories weren’t vanity, but a truth for the tribes, a voice that shaped how people saw the worlds and the artists who mattered, a business reporter, a major label department head who hated the way decisions were never for the artists, a boutique artist development and media relations innovator who’d fight for her clients, a battered survivor of a callous industry, a truth-teller when it mattered – and nobody wanted to listen.

It got crowded in that row. But it also got epic, because Jimmy Buffett had also flown into headwinds over and over again. He never won a Grammy; only had quantifiable hits on country radio with people like Alan Jackson. He didn’t care.

Jimmy Buffett believed in his songs, his friends, the characters who’d inspired him. As long as he had those people, a little imagination, he’d find a way. Oh, and that way made him a billionaire; he had the last laugh on the music business know-it-alls.

Not that that was his motivation. Standing onstage, with the smile slicing his face like wide open like a ripe mango, eyes sparkling at the naughtiness of Parrotheads converging on Paris in some kind of electric mojito acid test, there was revelry to be had – and songs, poetic and ribald to be sung.

That way the joy and the mission: honor what is however it was, remember the beauty, hang onto the high jinks and never, ever doubt the songs.

For someone who tilts at windmills, gets treated more poorly than people would ever imagine, whose best friend once squealed – driving around the streets of LA as two unhinged medium-20-somethings – “You could be HER, Holly Gee!” as Dylan’s “Sweetheart Like You” poured from her tape deck, La Cigale took back that fate which stretches you across a rack until you break and gave me back the effervescent joy of serving the music. That was what it’s about...

Even when the king of the parrot pirates was out flying his planes or chasing the sun, talking about good times or creating more memories, he was always braising those songs. Living like he sang, laughing like he wrote, it was all the same beautiful ecosystem so many people drew their moments of release, of elation, of crazy wild “oh yeah” from.

It was money I probably shouldn’t have spent, but it was the best value I’d seen in a long time. On the plane back, I smiled and exhaled and mindfully let all the good that is my life flow through me. “This is what being present feels like,” I marveled.

Jimmy Buffett, more than anything else, was absolutely, truly, completely present. Like his friends from Key West, adventurers all, he understood: Immersion is everything. Dive deep. Go big. Go crazy. Have fun. Feel it all, revel in it – and let what makes you feel alive be your navigational buoy.

It was a lesson that mattered profoundly.

When the call came at 5:11 a.m. from Kenny Chesney who’d texted me the night before, he didn’t have to speak. Just “he’s gone,” and gravity fell out of the room. It was dark, too early for morning to even think about breaking, and yet...

When we hung up the phone, I pulled the new rescue spaniel to me. Petted his silky head and felt tears fall off my face onto his ears. “Oh, Corliss,” I told the little guy, “you have no idea. To find someone who lived as most artists who pretend to, who embodies all the happiness that comes from being present, who wrote about places that mattered and being ripped down and forgotten...”

So many songs, so many moments, so much life.

And not just Buffett’s, but our own. I found “He Went To Paris” rising in my throat. Not because I called it up, but something in my muscle memory sent it through the transom. Singing softly to a red cocker spaniel who was licking the tears from my face, I couldn’t believe when I got to the end...

There it was: the words the old man, who’d seen World Wars, the Spanish Civil War, great love and horrible loss, had told Buffett more than half a century ago. Suddenly, there was the elegy for us all.

“Jimmy, some of it’s magic, some of it’s tragic
“But I had a good life all the way.”

www.hollygleason.com