My grad school pal Dave "Dave" Koukal turned me on to Wilco years ago by playing their 1998 album Summerteeth when I was visiting. I immediately bought the album. Some time after that my college pal Bobo the Wandering Pallbearer sent me a copy of Yankee Hotel Foxtrot. I think Summerteeth is marginally better, but there are few albums by any band of any stripe that have as much of a damn-the-torpedoes feel as YHF.
This effect is due largely to the screechy guitar riffs that lacerate many of the tracks. I am not at all sure what Wilco were thinking of, other than to try something different - and that, I think, is related to the band's history. Emerging out of the breakup of alt-country-rock Uncle Tupelo, Wilco's frontmen Jeff Tweedy and Jay Bennett consciously and conspicuously made Wilco sound different. What's interesting about this is that they tried to sound different from themselves, or from an earlier incarnation of themselves. Making this record just about scuttled the band, as I understand the story. Bennett split; the rest of the band ended up having to buy their way out of their contract because the label hated it so much.
Wilco have good genes. Tweedy's songs have depth, humor, humanity; and they all clearly have deep connections to the history of rock and popular music. It shows up in their solid ensemble play and their soloing, but in particular in the compositions. On YHF, my favorites, in no order, are "Jesus, Etc.," "I'm the Man Who Loves You" and "I Am Trying to Break Your Heart." "Jesus, Etc." (I'll bet you a thousand dollars it got this title because of the first line, and nobody having a good option for naming it) has a repeated couplet and chorus that I adore:
you were right about the stars
each one is a setting sun
tall buildings shake
voices escape singing sad sad songs
tuned to chords strung down your cheeks
bitter melodies turning your orbit around
"I Am Trying to Break Your Heart" is (I hope) a tongue-in-cheek bit about how crappy people tend to treat one another in relationships, for no reason at all. "I'm the Man Who Loves You" has freaking horns on it, as well as a highly-distorted fuzz guitar solo that irritates neighbors at 100 feet.
I suppose what really makes Wilco is Tweedy's distinctive, slightly nasal tenor. At least, that's what I expect makes Wilco most recognizable. Either that or Tweedy's Eeyore-esque lyrics and (frequently) delivery. I think what makes Wilco great could also represent a catastrophe for rock music. They're sort of rock classicists, or mannerists: the stuff that makes rock rock, especially 60s and 70s rock, is, in Wilco, appropriated and distilled into an oddly matured music. Which might make Wilco Tchaikovsky, I'm not sure.