This was the first Wilco album I listened to, and (cliche, I know) was quite blown away. I was giddy for three days. Now I've been a shamelessly obsessive Wilco fan for 5 years or so, and can better digest what this album represents. Take the defining alt-country band Uncle Tupelo, launch a spinoff with Tweedy as frontman, Tweedy takes over, steers the band to ever more progressive obtuse pop. This is the first album where that direction was clear: the irrevocable departure from straight ahead roots rock towards an unknown realm of experimentation (though their latest work remains unapologetically listenable, unlike much of the other stuff promulgated by the likes of Captain Beefheart). Here we still see fairly simple country based ditties, but even in these is visible the desire of Tweedy and company to get a little darker, scarier, more surreal at times. There are upbeat rockers aplenty (Shot in the Arm, Can't Stand It) but listen to the lyrics and you'll see they're well beyond boymeetsgirl. There are breezy country-rock styled riffs, but again, scratch the surface and you'll hear Jeff Tweedy singing about growing old, fighting loneliness, etc. Bonus track Candyfloss is a shameless Beach Boys raveup, pure hyperglycemic pleasure. My two favorites are quite dark: She's a Jar (somehow it's about physical abuse and pervasive disappointment, though the lyric is a bit obtuse at times)and Via Chicago (darkest imagery, powerfully presented).
Even with the breakthroughs of Yankee Hotel Foxtrot and A Ghost is Born (their two subsequent albums) Summerteeth remains my favorite. The next two continue to depart from the pop mainstream while remaining quite accessible; Summerteeth was closer in, more comforting, more satisfying in a very basic way.