I just wanted to give the guy a little help. Helping him, I realize now, was always part of it.

How could I not want to help him? I felt indebted to him, felt I owed him some cosmic payback, ever since that day, early last year, when I found his music and it gave me a second wind, a much-needed burst of faith and clarity. I loaded his songs into my iPod and while living on the road, while sitting on planes and trains, while lying in strange motel rooms, I closed my eyes and focused on his lyrics and thought: This guy’s channeling the angels. This guy’s got the gift. This guy can conjure a heartbreak, a hangover, moonlight, the Deep South, with a few words. I wondered: Who is this guy? Who the hell is Jeff Finlin?

I assumed he was British, because he was so literate, and because three of his records were on a British label. But mainly because there didn’t seem to be any other explanation for his obscurity in the United States. Then I got home to Denver and discovered that Finlin was American. Not only that, he lived just north of me. In Fort Collins, of all places. Fate, I thought. Clearly I was meant to find Finlin.

He was a story, after all. A quasi-anonymous musical prodigy. An undiscovered Bob Dylan in the foothills of the Rocky Mountains. That was intriguing, that was news—and I was a journalist. Naturally I wanted to write about him. As for helping Finlin, that was a vague notion at best, a half-formed impulse in the back of my mind, easily rationalized because it seemed like no more than that basic reflex we often feel toward the great artist who toils in anonymity. Who hasn’t felt the desire to go back in time and float van Gogh a loan, give Mozart a steady gig, drag Emily Dickinson by her petticoats to a publisher?

Still, I see now, my gratitude for Finlin’s music grew, evolved, and ultimately complicated everything. In trying to help the guy, I made his life harder. In seeking to write about Finlin, I became the most recent of his many disappointments.

It began last fall, this Finlin fascination, and carried into winter, until finally I sent him an e-mail, telling him I was a reporter for the Los Angeles Times, and that I was interested in writing about him. He phoned me right away. I explained how I’d discovered his stuff while on the road and said I couldn’t understand why he didn’t have millions of fans. He laughed softly, and we made plans to get together soon.

While writing other stories I collected research on Finlin. I learned that, despite his lack of commercial success, he’d received plenty of lavish praise. He’d gotten reviews any singer-songwriter would kill for. Critics gushed about his vocal debt to Dylan, and noted his resemblance to other beloved troubadours like Steve Earle, Randy Newman, and Tom Waits. They called his lyrics “literature,” dispatches from the social margins, and compared his sensibility to that of iconic masculine writers like Raymond Carver and Sam Shepard.

I learned that the Oscar-winning director Cameron Crowe chose a Finlin ballad for the soundtrack of his 2005 film Elizabethtown. At the movie’s climactic moment Crowe set Finlin’s earnest, yearning, soulful voice in the background. But the voice, so strong, so raw, spilled into the foreground. It seemed fitting, poetic, that Crowe of all people had given Finlin his biggest break to date, and that so little had come of that break, since Crowe was also the writer-director of Almost Famous. I learned that Bruce Springsteen was a Finlin fan. At Springsteen concerts the walk-up music is sometimes a song by the almost-famous Finlin.

Then last February I saw my chance, the perfect peg for a Times story about Finlin—the Grammy Awards. With the music industry gathering in L.A. for its biggest night, I told my editors, I’ve got a story about a 46-year-old unknown who ought to be there, collecting Grammys by the armful, but instead, for some reason, will be watching the show from his house in Fort Collins. Sounds interesting, the editors said. Write it up and we’ll put it on A-1.

So I met Finlin for lunch at a sushi place in downtown Fort Collins. I liked him right away. He had flair. He wore a pale yellow blazer and purple eyeglasses. He looked like an artist. Then, as the winter twilight deepened, he looked a bit like Chris Isaak, with a few more clicks on the odometer, a few more disappointments under his belt.

I told him I was hoping to get his story onto page one. Better yet, I hoped it might run Sunday, the day of the Grammys, when millions of readers, including hundreds of music industry people, might see it. Great, Finlin said, but he sounded blasé. He didn’t really care about the Grammys, he said. He had no plans to watch. He just didn’t give a damn anymore about all that fame crap.

I asked about his life. How on earth did he land in this quiet college town, where the wind smelled like horses and the best-known musicians in the phonebook were the Subdudes? A natural storyteller, he started in medias res, and I had to coax him to go back to the beginning. He was born outside Cleveland, to a factory-supervisor dad and stay-at-home mom. From the start he felt restless, out of place, not all that happy. In his song “Love and Happiness” he wrote: “I was raised a pilgrim’s son / Saying I’m sorry for nothing I done.”

While just a teenager he hitched west. “If I’d been born in Melville’s time,” he said, “I would have been on the whale ships.” All his heroes were wanderers, especially Kerouac, and like them he took any odd job he could find as he crossed the country. Waiter, painter, farmer, bartender, dishwasher, even circus hand. Finlin’s main task was making sure the clowns always had enough tequila. “They were kind of angry clowns,” he said—and they grew angrier whenever the tequila ran out. He developed a bad crush on the contortionist, one of his many “twisted” romances, he joked.

He’d always wanted to make music, and in 1982 he ended up where half of all aspiring musicians seem to end up eventually—Nashville. He got a gig playing drums with a band called the Thieves, and they cut an album, which did well. But Finlin chose to strike out on his own. He’d recently fallen in love with a woman named Karen—they married three months after meeting—and he felt his own songs welling inside him. “I never wrote a song until I met her,” he said.

He was a 28-year-old singer-songwriter, a late bloomer by music industry standards, so his chances of success were slim. And yet he couldn’t stop writing. New songs kept coming to him. They fell from the sky like rain. “I don’t write them,” he said. “I just write them down.” Soon he cut his first record. It flopped, as did the next. None of his labels gave him any marketing. One didn’t even release his record. All that work—Finlin was devastated. He already drank, but he began drinking more, to cushion each blow, to keep the creative channel open, and also to shut it. “It was the only way I could turn off my mind,” he said. “I’d write all day, and the only way I could turn it off was to drink…. It’s a great tool to deal with your fears, your insecurity. It definitely works.”

Fatherhood changed everything. In 1995 Finlin and his wife had a son, Aidan. Finlin quit drinking. In his song “Sugar Blue Too,” he wrote: “The hole it’s big, it’s dark, it’s round / And you can’t fill it up with what you lack.” I asked if the lines were autobiographical. He said every line he ever wrote was autobiographical. I asked if he had a favorite bar when he drank. “My favorite bar,” he said, “was my couch.”

He and Karen decided they needed to break away from the Nashville scene, they needed something different, and in 2003 they moved to Fort Collins, where they found all the different they could handle. Among the cowboys and frat boys, Finlin definitely stood out. “When I got here,” he said, “people asked me what I do. I said, ‘I’m a songwriter.’ They said, ‘You need to get a job, dude.'”

But he’d already tried to go straight. Toward the end of his time in Nashville he decided that he couldn’t justify so much struggling and scrimping without any hope of success. He couldn’t support a growing family on almost-famous wages. “I learned a trade, had a little painting business. I said—I’m done with music. But it wouldn’t let me be done. The need to create is so strong. Even when I do something else it’s all I think about.”

He returned to the music, but this time he adopted a new attitude. He didn’t pine for fame, didn’t let himself get sidetracked by wanting and hoping. “Where there’s hope,” he said darkly, “there’s fear.” He no longer went to bed every night feeling angry at the world. “I spent 35 years being frustrated,” he said. “I had to make other choices.”

Some years he made a little money. Some years he made less. Karen, thank God, was always there to pick up the slack. Her salary as a nurse helped pay the mortgage.

In 2007, however, Finlin expected to bring in a bit more cash. He was getting set to release another record in the United States, Angels in Disguise. “I hope somebody plays it on the radio,” he said. “I just want to work.” There—he’d said it. Hope. And want. I called him on it. OK, he confessed with a grin, he hadn’t entirely quit hoping and wanting. “I’d love to buy my wife a car,” he said. “Pay off my motorcycle, ride horses, tour and have 1,000 people show up.”

But if none of that happened, he said, so be it. He no longer saw fame as the finish line. He worked hard at his art, but knew when to stop. He talked as though reading directly from the Tao Te Ching—”Do your work, then step back. The only path to serenity”—and the seeds of his fatalism-cum-Finlinism had been there for years. Sprinkled through his lyrics were many lovely descriptions of the special peace that comes from no longer giving a shit.

Ain’t nothing left to do but walk the streets so dark
And whisper I love you to a moment there inside your heart
Let the trumpets sound, but listen to the morning dew
And fill yourself with what you found,
And be my little sugar blue

After our lunch together, Finlin climbed into his four-year-old Honda CRV and I followed him back to his house. I said a quick hello to Karen, who was busy in the kitchen, and followed Finlin down to the basement, where a beat-up old table held a computer hooked to a stereo, and a keyboard stood against an exposed wall. My recording studio, he said with some pride.

Finlin’s 11-year-old son, Aidan, appeared at the bottom of the stairs and asked politely if he could play video games on the computer. Sure, Finlin said. A handsome kid, with hair nearly the shade of Finlin’s yellow blazer, Aidan quickly became engrossed in his game. I asked him what kind of music he liked. Without looking up he said, “Ukrainian techno.”

“Of course you like Ukrainian techno,” Finlin said. “Why wouldn’t you like Ukrainian techno?”

Aidan clicked the mouse a few times and a frantic house beat came thumping from the speakers. Over the shuddering thump thump I asked Aidan what he thought of his father’s music. Again he answered without looking up.

“It sucks.”

I phoned music industry experts and put it to them: With so many new avenues for musical artists, with iTunes and MySpace, “American Idol” and YouTube, why can’t Finlin find an audience? They said he might be too old, might have the wrong look, might just be unlucky. But they also said I shouldn’t buy into the myth that more avenues means more music gets heard. If everyone can be heard, they said, no one gets heard. The democratization of music can create a deafening roar above which original voices have trouble rising.

People familiar with Finlin’s work said his lack of success was a sin. “He’s the great lost singer-songwriter,” said Nick Stewart, former director of Rhino UK. Granted, Stewart was biased. He’d overseen several Finlin records. (“They did terribly badly.”) But he swore his judgment was objective. No matter who you are, he insisted, “you couldn’t possibly not get Finlin.”

Mary Martin, a former record company executive credited with introducing a young Dylan to his band, recalled the first time she heard Finlin. “I was astounded,” she said. “So absolutely in love with his poetry, his unique voice.”

Finlin reminded Martin of legends she’d known. Not just Dylan, but Leonard Cohen, Van Morrison. So strong was her belief in Finlin that she briefly agreed to manage him several years ago. The first thing she did was arrange a showcase for music industry big shots. Finlin gave an “astonishing” performance, Martin said. And the big shots?

They passed.

Why?

Martin didn’t know. She guessed, she worried, that Finlin was too literate. His lyrics, she said haltingly—they’re deep. Nuanced. Salted with allusions. In a culture growing less literate by the minute, she said, a well-read troubadour is a tough sell.

I wrote it up—Finlin’s journey, the experts’ praise, Crowe, Springsteen—and shipped it to L.A. Then, unexpectedly, my editors ran my story by the newspaper’s music critics, who savaged it. This guy isn’t unique, they said. Countless musical artists can’t get a break, they argued—why should we care about Jeff Finlin?

Because he’s great, I replied. Because if he isn’t unique, if there are countless Jeff Finlins out there, what better time to report on their plight than the day of the Grammys? And if Finlin is one-of-a-kind, aren’t we obliged to spotlight him, to feature this huge talent who somehow fell through the cracks? Isn’t that what we do?

While the editors and critics deliberated, I bundled up and went to hear Finlin perform at a bar in downtown Denver. It was a miserably cold Friday night, the temperature near zero. For some reason the bar had positioned Finlin and his band—a group of local players with whom he sometimes gigs—beside the front door, so that whenever someone went in or out, which was every four seconds, an arctic blast rushed in and seemed to freeze the music in midair. Also, to set the mood, someone had arranged candles all around the barroom. But this actually served to ruin the mood, since gusts from the perpetually open door made the candles constantly gutter or blow out.

Unfazed, Finlin strapped on his big old guitar, the one with the crack under the bridge (Aidan dropped a toy on it years ago) and sang his guts out. He gave a stirring performance, flinging his verses like bouquets into the half-lit barroom, even though only a dozen people were draped along the bar, ignoring the band, ignoring the arctic blasts, ignoring everything but the chemicals they required to stay warm and high. I, however, hung on every note. I never liked Finlin’s stuff better, and I prayed that the newspaper would run my story.

The next day the newspaper killed my story.

I didn’t know how to tell him. I paced the house all weekend, rehearsing what I’d say. I picked up the phone, put down the phone. Finally I took the coward’s way out, sent Finlin an e-mail. I wrote that I was disappointed, angry, for both of us, and deeply sorry. He e-mailed back right away. Don’t sweat it, man. “It all works out the way it’s supposed to.”

I didn’t talk to Finlin for months. Then, one day, living on the road again, I was fiddling with my iPod and stumbled on those Finlin songs, the ones from his finest record, Somewhere South of Wonder, and again he lifted me right out of my fatigue, out of myself, nearly out of my airplane seat. I vowed that as soon as I got home I would dig out my Finlin story, find it a proper home. I e-mailed him and asked sheepishly if he was game, if he was willing to give me one more chance, and he said sure.

We met for sushi again, a cold spring night in Fort Collins. He looked well. He looked happy. He’d been painting houses all day, up near Red Feather, and after hours of watching the osprey pluck trout from the lake, after holding his face to the high mountain sun, Finlin radiated a deep contentment. Also, he reported cheerfully, he’d recently played a big concert in Knoxville, as the opening act for James McMurtry. Better yet, his new record was out. Though his label was taking a somewhat “mellow” approach to marketing it—I laughed—he held out hope that a song or two still might somehow find its way onto the radio.

If not, he said, so be it. “There’s nothing that’s going to happen in my life that’s going to make me any safer,” he said. “Nothing I’m going to accumulate that’s going to keep me from dying like everybody else.” Besides, he was already absorbed in the next record. He’d written 30 songs he liked, and the challenge would be winnowing them down to a dozen. He planned to descend to the basement soon and begin recording. He’d even thought of a title—Ballad of a Plain Man.

As Finlin talked about his work, I heard as always the distinct echo of Dylan, but also Walden. I recalled the first time I’d read that marvelous book, and the first time I’d read the letters of van Gogh, and the journals of Delacroix, because Finlin exuded that kind of monastic devotion to craft, that artistic purity. Once more I asked how he’d achieved this enviable calm, how he managed to remain so serene on the razor’s edge of failure and fame. “It’s beyond my control,” he said. “If I chase it, it runs away. The only thing I have control over is the work.”

Finlin loved books too, and he’d read everything. We talked about some of his favorites. Henry Miller. Allen Ginsberg. Charles Bukowski. They all struggled, starved, before achieving success. Then again, Finlin said, how much did their success matter when all was said and done? “Let’s face it. Most people today don’t know who the fuck Henry Miller is.”

If you’re chasing success, Finlin said, you’re chasing an illusion. (In “Alchemy” he wrote, “I’ve seen the order in confusion / The empty hand behind illusion.”) And if you quit because you haven’t grabbed hold of that illusion, then you weren’t meant to create in the first place. “Most people who don’t have any success, they just quit,” Finlin said. “They’re not true artists. Jung says: The artist is the only person who will compromise his well-being to create.”

After dinner we shook hands and said goodbye. I told Finlin I’d be in touch, and watching him disappear down the dark street I understood for the first time how large a part gratitude had played in my reaction to him. But also rage. Subconsciously I wanted to help the guy, but I also wanted to unleash a primal scream on his behalf, on behalf of everyone trying to sing or say something honest in this Lindsay-loving, Rosie-riveted, Sanjaya-saturated culture. As a journalist I’d been curious about Finlin—as a writer, however, I’d been furious. All the rage Finlin didn’t feel, I’d felt for him. He was a legitimate news story, he warranted a profile, but at last I recognized that I’d let myself become offended, personally offended, by his lack of success. Finlin’s website got 6,000 hits each month while “American Idol” got 60 million votes in one night. When I compared those two numbers I couldn’t help but grind my teeth.

Driving back to Denver, hitting the scan button on the radio in search of something good, I reviewed my history with Finlin and shook my head. I’d tried to write about him—and failed. I’d tried to help him—failed again. I’d raised his hopes—and dashed them. Now, even as I planned, consciously this time, to help the guy, I saw that once again he’d helped me first. He’d prompted me to do a badly needed overhaul of my views on failure and success, criticism and creativity, writing and rejection, commerce and art, and in so doing he’d inspired me, steeled my nerves and lifted my spirits—on the eve of a major decision.

The Los Angeles Times, to save money, to stay afloat in a culture that reads less, was offering buyouts, and days after my dinner with Finlin I took one. I filed the form asking for “voluntary separation,” fancy words for my walking papers. I would have done it anyway, Finlin or no Finlin. But he made me breathe a little easier, stand a little straighter. He made me feel braver about striking out on my own, going solo. In his song “The Hard Way,” which could be his anthem, and might be my maxim, Finlin wrote: I don’t know what’s right or wrong / So you sure won’t learn it in this song / The only way is to follow your heart, / In this dog-eat-dog world I think that’s smart.

I didn’t know how I’d earn a living. The only thing I knew for sure was that I wanted to write what I wanted to write—and that the next story I wrote would be the ballad of an almost-famous man.

And regardless of my new Finlin-inspired Taoist outlook—”Do your work, then step back”—I knew that when I finished the story, when I let it go out into the world, I would permit myself to hope that many people might read it. And that a few of them might be inspired to give Jeff Finlin a little help.

Pulitzer Prize-winning writer J.R. Moehringer is also the author of the best-selling memoir The Tender Bar. A motion picture, Resurrecting the Champ, based on one of his nonfiction pieces, is set for release in late summer. This is his first article for 5280.