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Twenty years into a mighty, if relatively unsung career, first as an act called Smog, latterly under his own name, Bill Callahan’s oblique, deadpan, understated songs mark him out as one of the most penetrating crafters of the North American language since Leonard Cohen. Dream River, Callahan’s 15th-odd album, strengthens that claim further with an album about flying, dying and painting boats. Naturally the painting of boats proves the most cosmic of these activities.

If phrases like “and mountains don’t need my accolades” send a frisson to your antennae, you have a friend in Bill, a writer who can make your jaw drop mid-song, such is the power of his aperus. Well, “a friend” might be pushing it. Callahan has always been a writer capable of skewering, but he’s hardly clubbable. Bathysphere, from 1995, could be the national anthem of all introverts who have a thing for the sea. In it, the seven-year-old narrator asks his mother to lower him into a bathysphere. “And if the water should cut my line, set me free,” sings Callahan, matter-of-factly, “I don’t mind.” The chorus is a series of gasps for air: “Ah, ah, ah.”

But despite the resonance of his writing, the studied detachment with which Callahan operates can almost feel reptilian; his views on love are more often discomfiting than comforting. The downright creepy Dress Sexy at My Funeral, from 2000, is one of his better-known cases in point; the penchant for al fresco sex exhibited by Callahan’s narrator continues on this album’s fine cut, Spring. Outside song, Callahan is the kind of enigma you feel you shouldn’t probe too deeply – one whose relationships with notable female creatives including Chan “Cat Power” Marshall and Joanna Newsom haven’t always painted him as the cuddliest of boyfriends. (By the by, Cat Power’s 1996 version of Bathysphere is also a treat.)

Every album since Smog’s establishment has packed a handful of songs where the untold drama of events unfolding offstage often has the power to pull the rug from under the listener. But now Callahan is even better – his voice deeper, his hand steadied by years of operating, and his words now functioning as though synchromeshed with the music. The arrangements on Dream River are almost as eloquent as his lyrics. Callahan used to fit loosely into some lo-fi, writerly Americana continuum with Will Oldham and Mark Kozelek – racked men accompanied by guitars. These songs, by contrast, have lots of flutes and hand-drums on them; the sinuous roll of songs like Javelin Unlanding and Ride My Arrow (almost West African in their cadences) beautifully maps the flights of the titular objects and provides an exotic counterpoint to the all-American subject matters in which Callahan deals. When Callahan sings: “I don’t ever want to die”, an echo of percussion rattles like bones. There is even a dub version of Javelin Unlanding, sadly not included on the album itself.

Words and music pull together most heroically on Summer Painter, Dream River’s centrepiece, another all-time Callahan classic. In it, Callahan is a guy doing up boats. He’s “made some dough, socked it away/ Always said, for a rainy day”. That day comes, and when the hurricane “rips the lips off the mouth of the bay”, flutes and guitars and drums rise and rise, forcing his matter-of-fact delivery up to a rare gale itself. The calm afterwards is every bit as transcendent.