Even if general critical opinion of Wilco’s Summerteeth is positive, the album is destined to be dwarfed by its immediate predecessor and successor—1996’s folk-rock opus Being There and 2001’s Yankee Hotel Foxtrot, an endlessly praised high point in Wilco’s career. This makes sense to a degree, as Summerteeth is not as earnest or performance-perfect as the former, neither is it nearly as experimental or successful in cultivating a single mood as the latter. Apparently, the midpoint between these two poles is something unlike either: a lengthy album of sunny kitsch. The tracks on Wilco’s 1999 release embrace a radio-pop sensibility, delivering what are essentially lost ’60s gems filtered through an orchestral sound palette and an early exploration of the intersection of rock and electronic music-making.

Multiple guitars, chimes, drum set, organ, banjo and synthesized strings—at least—all appear in the first ten seconds of the album on “Can’t Stand It.” This opening is split between two seemingly unrelated phrases, one grandiose, passionate pop, the other a campy country bounce. The following hour, complete with “hidden” tracks and remixes, carries through with this obsessive approach to filling space. The combination of this gleefully omnivorous arranging and the earworm hooks give Summerteeth an optimistic feeling, even if Jeff Tweedy’s lyrics look at life and the breakdown of relationships with a self-destructive and often macabre tone.

The defining sound and style ofSummerteeth stems from its methods of origin. The album was among an early handful of indie releases (others by Tortoise, Stereolab and Everclear) that explored the then-new multi-tracking and production tricks of Pro Tools and digital editing. The audible evidence is plentiful. The album’s seemingly bottomless instrumental and effects bank feels like the product of a group of kids with fresh toys, especially in the case of Tweedy and the late Jay Bennett, who most actively produced the album. These two multi-instrumentalists were determined to use this newfound ease of layering to get the absolute most out of each moment.

Retrospectively, there’s an almost senseless, “because-we-can” mentality to some of the arrangement choices, the worst of which threaten to bog down Tweedy’s air-tight songwriting. This reads as a huge misfortune, as his core ideas and his vocal chops are both in practically flawless condition throughout. The opener “Can’t Stand It” is an impassioned ballad, but some of the impact is lost on repeated listens as the unnecessary filters and effects bury the nuances of Tweedy’s vocal performance. “A Shot in the Arm” captures the paranoia and self-hatred of a breakup with chilling precision. Presented in two versions at either end of the album, though, both rely on over-the-top strings and timpani that don’t match the confessional nature of the track’s message.

When the overtly studio-constructed sound settles into something resembling a live feeling, the connection between Wilco’s explorative sound worlds and Tweedy’s tried-and-true folk songwriting strengthens. “I’m Always in Love,” with its spacey synths and warm distortion, owns its own simplicity and makes an endearing case for hopeless romanticism. “How to Fight Loneliness” balances glitching, speed-warped keyboards and despondent country balladry, providing a dusty musical background that perfectly suits Tweedy’s wandering and hopeless narrative. “She’s a Jar” and “Via Chicago” are two stunning ballads, with Tweedy embracing unlikable narrators over beds of noise and flowery orchestral writing, creating something uncomfortably heartwarming and musically stunning.

If the overall hope was to use the digital studio as a unique instrument, the effect is a bit more distracting. The down-to-earth, Midwestern charm that defines so many of Wilco’s best material is buried beneath an overreliance—and ultimately misused, as some of the choppy jump-cuts show—on nascent technology. Enlisting Glenn Kotche and Jim O’Rourke, both traveled musicians in more avant-garde circuits, for the next few albums helped turn the experimental studio approach of Summerteeth into a more unique language built on the blend of noise and pop-rock, the true capacity of which is merely glimpsed at here.

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