Bonnie "Prince" Billy and a big fat bowl of Froot Loops
› firstname.lastname@example.org 
SONIC REDUCER Skip the cherries — life at times seems like a big fat bowl of Froot Loops — the type that figure-eight, undulate, and connect in the most unpredictable ways. For instance, Bonnie "Prince" Billy, né Will Oldham, and his ungainly, increasingly ecstatic shadow folk-country — that association's only right and natural. Oldham and Gen X cinematic hot-spring stoner sagas — it's altogether plausible. But Oldham and Diddy, the Bad Boy impresario identified in his own PR literature as a "mogul" before proffering the job title "artist" — huh?
What could these two possibly have in common apart from their age, 36? It's a logical leap if you study Diddy — arriving about two hours late for his recent roundtable interview at the Ritz-Carlton with absolutely zero Burger King Whoppers for yours truly and the other journos who were ready to gnaw their own typing arms off in hunger and antsiness. Instead the mogul packs a makeup artist and hair man (who brandishes a far-from-puffy comb — sorry) and plays us no tracks from his new, still-scarce album, Press Play (Bad Boy/Universal), yet carries it in his bejeweled hand like a salesman. (Perhaps in answer to the inevitable query: with fashion design, artist development, reality TV, label jockeying in his past, and DiddyTV on YouTube currently serving up alleged shots of Sean in the john, why does he even bother making an album? Diddy's comeback: "It's a gift and curse, because I do so many things. I'm making sure people know how serious I am about music.")
Well, Diddy and Oldham name games are the most obvious thread. Like Diddy, a.k.a. Puff Daddy, a.k.a. P. Diddy, a.k.a. Puffy, a.k.a. Sean Combs — Oldham is a man of many hats, personae, songs: a humble troubadour, a rambling tangent-exploring interview, a perpetual touring player, a before-his-time out-folker, a Hollywood-shunning onetime teen star of Matewan. At one point it seemed like he had a recording name for his every sound, if not every album — Bonnie "Prince" Billy was just the latest handle in a line that included Palace Brothers, Palace, Will Oldham, and at least one disc that sported no name at all. It was disorienting, delirious, and hard to track, and at times it just made you want to throw your hamburger mitts up, shave the nearest beard, and beat yourself around the face and neck.
Oldham probably feels much the same after fielding the same question repeatedly, explaining that he once thought of his albums much like films or plays and wanted to label each uniquely. "I thought it would be a way of focusing things on each record," he says from his native Louisville, Ky. "People would say, 'I like this record,' rather than 'I like the music of ...’ I didn't realize that it was sort of a definitely pointless battle — to see about maybe trying to make people focus on records as independent entities rather than representations of an individual's or group's work, and it became sooo energy-expending to always explain this name thing. I was finally just, like, 'This is just bullshit.’"
And if Diddy and his whirlwind junket offered little apart from the lingering impression that for some reason it was critical for him to leave the scent of power and money (he's reportedly worth $315 million) on local media — then Oldham is his opposite. On time and generously unearthing the contents of his mind, he's disarmingly candid and eager to dive into the depths of his past, untangling his feelings and thoughts about acting, recording, and mentoring (he famously championed a solo Joanna Newsom and played her music for their label, Drag City). Yet unlike Diddy, who appears to be jetting around the country in search of the artistic credibility he first found in music as a producer, Oldham has never been more on top of his so-called game.
His new album, The Letting Go (Drag City), is the worthy, relatively full-blown, and outright beauteous studio follow-up to his 2005 stunner Superwolf with Matt Sweeney. This time Dawn McCarthy of the Bay Area's Faun Fables leaves her imprint — her vocals echoing somewhere in the vicinity of Sandy Denny and Joan Baez. Under the gaze of Icelandic producer Valgeir Sigurosson (Björk's sometime engineer whom Oldham met while touring with the swan queen), The Letting Go is awash with melancholic melodic Southern rock and blues-folk, tunes that revolve around cursed love, child ghosts, and frosty wakes. Captured in Reykjavík and decorated with an image of Makapu’u beach on Oahu, The Letting Go doesn't sound on the surface like the product of volcanic island ramblings and rumblings — but its lyrics do hint at the tragedy of believing that each man or woman is an island.
That's why Oldham has gone out of his way to introduce performers like Newsom and McCarthy to his audiences. "Part of it is to reveal how interconnected things could be if you want them to be," he explains with a soft Southern drawl. "Part of it is also, if the world isn't going your way and there's a certain amount always of loneliness to do battle with, sometimes you realize it doesn't have to be that way. You don't have to be this solitary figure in the world." The yearning to connect, this time with an old friend, surfaces in Old Joy, a film by Kelly Reichardt (River of Grass), which has caught praise on the festival circuit for its rapturously, deliberately paced meditation on two men's slow-growth rambles through old-growth Oregon wilderness. Oldham's first substantial starring role since Matewan (he most recently appeared in Junebug), his character, Kurt, is a slacker gone to seed, soon to be homeless, and still in search of his next high, his next life lesson, his next brush with grace. After helping Reichardt brainstorm hot-spring locales in Kentucky, the man who could have ended up like Macaulay Culkin or so many Coreys — and instead laid down the blueprint for, one imagines, Jenny Lewis — accepted the part. "I knew Kelly was going to be working in a way I like to work, which is just like a full immersion process," he says, making the connection much as he pulls together Old Joy, his 1997 album, Joya (Drag City), Madonna, Emily Dickinson, and The Letting Go. "Everybody goes there. Everybody's basically on call.... The line between tasks is a semipermeable membrane. That's how I like making records too." SFBG
BONNIE "PRINCE" BILLY
With Dark Hand and Lamplight and Sir Richard Bishop
Oct. 30–31, 8 p.m.
Great American Music Hall
859 O'Farrell, SF
For more on Will Oldham and Diddy, go to www.sfbayguardian.com/blogs/music .