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When Gastr del Sol broke up in 1997, no one would’ve pegged Jim O’Rourke to become any kind of great pop hope. Of Gastr’s two permanent members, guitarist-vocalist David Grubbs—mastermind behind mid-’80s populist-punk band Squirrel Bait and the fashionably heavy late-’80s outfit Bastro—seemed more likely to be the one behind the most accessible elements of the Chicago avant-folk band’s four full-lengths. After all, O’Rourke’s nerdy pre-Gastr history found the bespectacled guitarist indulging in often-noisy experiments with industrialists Illusion of Safety, free-improviser Henry Kaiser, and metalhead KK Null. Surprisingly, though, with the release of 1997’s Bad Timing—the first in a trilogy of similarly packaged albums that also includes 1999’s Eureka and the new Insignificance—it became clear that O’Rourke’s emergent gift for hook writing was largely responsible for the crystalline pop sensibility of Gastr’s best and final effort, 1998’s Camofleur.

Chock-full of acoustic guitar, pedal steel, and horns, the four long instrumentals on Bad Timing made a crucial connection between John Fahey’s country blues and Philip Glass’ modern-classical minimalism. Charting a course from melancholic hammer-ons and heartache (“There’s Hell in Hello but More in Goodbye”) to jubilant marching-band brass and getting-the-fuck-over-it (“Happy Trails”), Bad Timing is immediately appealing and often shockingly beautiful, whereas Gastr’s discs can be frustratingly oblique. It’s also deceptively complex, building from simple, mountain-music guitar figures into strata of major-key bliss.

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Eureka brought an even more detailed approach. Newly influenced by orch-pop icons Van Dyke Parks and Scott Walker, O’Rourke expanded his musical palette to include syrupy vocals, layers of strings, and even cheesy CHiPs-chase-scene sax soloing. And whereas Bad Timing is pervaded by a sense of loss—all crying-in-your-beer song titles and pensive melodies—Eureka positively reeks of possibility. On “Prelude to 110 or 220/Women of the World,” O’Rourke, doing his best Helen Reddy-goes-indie impression, urges “Women of the world take over” as the folky hook spirals into bright harmonies. On “Eureka,” he asks over a crackling telephone line (a la Bad Brains’ “Sacred Love”), “Hello, hello, can you hear me?/Are your skies clear and sunny down there?” before the music swells into luminous brass and percolating electronics. And he even included a saccharine, hipster-alienating cover of Burt Bacharach’s “Something Big” (“There’ll be joy/and there’ll be laughter/Something big is what I’m after now”) to hammer home Eureka’s warm vibe.

But O’Rourke just sounds bummed on his latest. Set against a glorious guitar line that’s equal parts Allman Brothers and the Band, the first few lines of Insignificance’s opening cut, “All Downhill From Here,” portray a relationship in its death spiral: “Don’t believe a word I say/Not that you would anyway/I may be insincere/But it’s all downhill from here.” Things obviously ain’t gonna get better, but to judge by the anthemic “hoo-hoo”s and the almost-metal guitar chug, O’Rourke sounds great going down.

The brave new O’Rourke has decided to dump more than just his girlfriend: Although Insignificance retains the pop hooks of its predecessors, it jettisons the baroque instrumentation. “Insignificance,” the Beach Boys-esque second track, is uncharacteristically straightforward pop, with sturdy piano and waltzing drums driving O’Rourke’s lonesome thoughts: “Failed once again like a friend who needs you.” But “Therefore, I Am,” which follows, is the tautest of the lot: Over distorted, Wire-like chording and insidious “oooh”s, O’Rourke, observing that he and his soon-to-be-ex “are on a sinking ship,” wonders, “I’ve seen so many things/Why am I talking to you?”

Insignificance may be the closest O’Rourke’s ever come to rock ‘n’ roll orthodoxy, but the guy still can’t take off his thinkin’ glasses. Like Bad Timing (the left-field brass blast on “Happy Trails”) and Eureka (the cornball lyrical gag on “Happy Holidays”: “I’m going to a place where the women have nothing on…but the radio”), Insignificance is rife with jokey surprises: the wistful folk interludes on “All Downhill From Here,” the cheery whistling birds on “Insignificance,” the disc-closing noise finale of “Life Goes Off.” And the disc’s bitterest song, “Memory Lane,” is well-trafficked with turnabout couplets: “These things I say might seem to offend,” O’Rourke deadpans early on, “but not half as much as I’d like to intend.” In the chorus—propelled by a sparklin’ guitar hook courtesy of Wilco honcho Jeff Tweedy—O’Rourke cattily comments that listening to his ex makes deaf folks seem “so damn lucky.” Later, he recalls the brilliance of her visage: “Looking at you reminds me of looking at the sun”—but then pauses and adds “too long” as the guitars thin out, giving way to Chicago Underground Trio cornet player Rob Mazurek’s smeary lines.

But the biggest surprise this time around is O’Rourke’s almost generic classic-rock-isms. The most obvious examples are the Southern-rock flavor of “All Downhill From Here” and the arena-sized riffs on “Therefore, I Am.” But “Get a Room”—which invests heavily in a rudimentary VH1-esque progression that would put Sheryl Crow to sleep—can’t manage the same kinda High Life-poundin’ fun. It just sits there, inert. Even the song’s more typically O’Rourkeian coda—which weaves in cornet and vibes as our hero’s relationship slips away (“And now you can’t see her/All you see is a timer”)—overstays its welcome, becoming too friggin’ long and repetitive to save this middle-of-the-road throwaway.

It’s not as if this thing sounds like Thin Lizzy. But it’s easily O’Rourke’s most user-friendly effort yet. And most of the time it works: In a just world, “All Downhill From Here” would be cranking in muscle cars from Manassas to Mobile. Even when O’Rourke’s new rockist approach briefly falters, it’s only a minor distraction from the disc’s pop charms. If Insignificance isn’t the highlight of O’Rourke’s trilogy, it’s only by virtue of some stiff competition. CP