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This past August, singer/songwriter Will Oldham stopped by the Los Angeles recording studio where Johnny Cash and producer Rick Rubin were finishing work on the third album in Cash's American series of albums. Oldham knew that the Man in Black had already recorded his song "I See a Darkness" at a session back in Tennessee. He also knew that Cash and Rubin recorded lots of songs for each American album, only to winnow them down to a handful for each release. Despite nearly a decade of writing and recording under various monikers (including the Palace Brothers and Bonnie "Prince" Billy), Oldham didn't have his hopes up. He just wanted to meet one of his idols.

It turns out that Cash was unhappy with the scratch, or practice, vocal he had recorded for the song. Before Oldham knew it, he found himself in a vocal booth laying down a high, trembling chorus harmony behind Cash on the version of "I See a Darkness" that turns up on Cash's new American III: Solitary Man (American). But not before finding himself in the unnerving position of having Johnny Cash ask him how to sing it.

"He would ask me things about what he should or shouldn't do. There's one line where he talks, and there's another line where he changes the timing a little bit, and he asked if it was OK," a still-awed Oldham says. "And it was just so obviously right, the way he did it. I just didn't feel like I had the authority to answer the question, but I was the only person being asked so I had to answer the question. It made me feel so bad in a way, because I felt like I was speaking out of place. It was a wild day."

The 29-year-old Oldham is among heady company on American III. His song sits alongside compositions by Tom Petty and Jeff Lynne, Neil Diamond, U2, Nick Cave, David Allan Coe, and, of course, Cash himself. But it is Oldham's "I See a Darkness," a stumbling admission of vulnerability wrapped in a declaration of boon friendship, that provides the album with its singular moment of genuine emotional lift-off. And the track's success owes as much to Oldham's power as a songwriter as it does to Cash's power as an interpreter. Hearing the song coming out of someone else's mouth only underlines its odd intensity.

Oldham tells the story of his head- spinning trip to L.A. from inside Ghion's Ethiopian Café, a tiny restaurant and bar a short stroll from the Meyerhoff Symphony Hall. Oldham moved to Baltimore from his last home base in Alabama around Thanksgiving of last year, to be close to his brother Ned and his fledgling family, who moved here shortly beforehand. (Ned Oldham, a singer and songwriter in his own right, leads the band the Anomoanon.) The city's cheap housing stock and proximity to major travel hubs also proved an attraction for a successful-though-far-from-platinum-selling musician who tours frequently. But more than a mere convenience, Oldham seems excited by Baltimore, from the exotic yet workaday feel of Ghion's, where the proprietors' warm welcome marks him as a regular, to the city's arts scene.

"The people who are involved with music and other artists [here] seem to have more flexibility than they do in a lot of places, and a wider range of ways of expressing themselves" he notes. "It seems very free-flowing." Letting slip a tight grin, he goes on to list among Charm City's other charms "not an excessive amount of idiots, probably because it's not the easiest place to live in other ways. So if you want to do something stupid, you go somewhere stupider, like New York City."

Oldham came of age in Kentucky where, after a turn at acting (see John Sayles' Matewan), he began to get serious about writing and performing his songs. He assembled a bunch of his musical friends from Louisville to record a single and the albumThere Is No-One What Will Take Care of You (Drag City) under the name the Palace Brothers in 1993. These recordings first introduced his mercurial warble, his strangely poetic and enigmatic lyrics, and the often indefinable emotional territory his songs tend to explore. With its banjos, ersatz mountain gospel numbers, and sounds of a crackling wood stove, There Is No-One also inadvertently helped kick off the boom of would-be rustics in '90s indie rock.

But as his successive singles and albums showed, Oldham quickly moved beyond any but the most elementary connections to Appalachia or the usual parameters of the indie scene. Played by an ever-shifting roster of musicians and released under ever-shifting variations on the name Palace, his recordings quickly outstripped any genre descriptions or imitators. Over the course of dozens of singles, EPs, albums, and compilation tracks, Oldham has created a carefully tended, rigorously pursued body of work that nonetheless sports a tentative, hard-to-pin-down quality. His songs often sound intimate, confessional even, but the details of the situations depicted are sketchy and often contradictory. Yet something in the vague, almost accidental quality of his best songs gives them an enormous power that a more studious approach might overshoot.

Asked about the balance between craft and intuition in his songwriting, Oldham offers a long, thoughtful pause before answering. "In order to get anything out of it, it's nice if it's as much of a balance as possible, I think," he says with some caution. "If it was all craft or all intuition, it could lead one too far away from something valuable." While he admits that hearing, say, a country songwriter define and evoke a specific emotion in a song impresses him, "I'm not a person who always knows the way I feel. I often feel emotionally overwhelmed, but I don't exactly always know why. All the reasons to hate or be happy or whatever seem so intertwined and overlapping.

"I know exactly what I felt emotionally on earlier recordings, because I knew more about my own emotions than I did about the music," he says of his songwriting process. "But as I learn more and get a kind of fluency, and everything I know tells me that a song functions, that it's good, then I think it is too disconnected from intuitive emotion. Say I work on a song for two months. Have I overworked the song, or am I making it better? Oftentimes it turns out I have made it better. But I always worry that I haven't, that I'm being stupid and haven't given it its due."

At the same time, Oldham acknowledges, the more mysterious elements of his own work keep things interesting. "It's good after each show to think, Why do these songs work, or not work?" he says. "If you know exactly, then it's not all that exciting to know that you have three more weeks of performing these songs every night."

Oldham's two most recent recordings find him experimenting with craft and intuition more overtly than ever. In September, the Chicago-based indie label Drag City released All Most Heaven, an EP that found Oldham collaborating with producer Rian Murphy and the likes of the Sea and Cake's Archer Prewitt, Bill "Smog" Callahan, Jim O'Rourke, and Stereolab's Laetitia Sadler. Meanwhile, Oldham's own Baltimore-based Palace Records offered Get On Jolly, an EP collaboration with Dirty Three guitarist Mick Turner (aka the Marquis de Tren) featuring lyrics Oldham (under his Bonnie "Prince" Billy moniker) adapted from Bengali writer Rabindranath Tagore.

All Most Heaven is perhaps the most overtly lighthearted (even lightheaded) project to ever feature Oldham's name, from the cover photo of him and Murphy mugging it up as Edwardian lords to its jaunty pomp-pop songs, complete with strings and French horns. The lyric sheet credits Oldham with lines such as "We held upon a biggun daddy/ hates to, he song fail on/ the gable/ ah hee ape-hole." He insists that the words are not improvisations, that they were "written and sung again and again and again, always the same way." He says that the idea was to "make a kind of ideal song that was completely unencumbered by its lyrics--but that still had lyrics--and had some ideas drifting in and out. Like taking Mick Jagger's singing one step further, you know? Instead of not enunciating, just have words that aren't there."

Get On Jolly, on the other hand, represents the first fruit of several attempted collaborations with Turner, whom Oldham met in a London pub years ago. The guitarist, Oldham says, "makes music piece by piece, with lots of loops, not thinking about structure beforehand, and I think a lot with song structure." Presented with tapes of more than an hour of Turner's ruminative guitar work, Oldham says, he "wanted to figure out how to make a progressive lyric over music that is not necessarily progressing in that way." He happened to be reading a collection of Tagore's short, devotional prose, which he ended up adapting to fit Turner's tracks (the numbered song titles refer to the Tagore passages used for each track). The EP works best when the music and words fully integrate into songs--as opposed to "spoken-word" pieces--and the resemblance between Tagore's quietly ecstatic musings and Oldham's own lyrics is uncanny.

It's not surprising to hear that Oldham once recorded an entire unreleased album with Turner's steady gig, the Dirty Three. Like Rachel's, Godspeed You Black Emperor! (see Music, page 32), and a handful of other '90s instrumental outfits, the Australian violin-guitar-drums trio creates very emotional music that doesn't go out of its way to define the emotions in question. The fact that Oldham does the same thing while hemmed in by lyrics makes his career to date even more impressive.

"It sucks to listen to music where you feel beholden to the singer, where you feel like they're doing everything for you," Oldham says when the discussion turns to songwriters with a penchant for the unpredictable and ambiguous, such as Neil Young and Joe Henry. "You make the song work, or not work. They basically [do] something that [says], 'This is for you. If it doesn't work, it's because you didn't feel it was worth working for.'"