The Post ranks the Wilco albums:
1. "Summerteeth" (1999) The album that bears the least resemblance to any other in the catalogue is the best. Their third effort was the first that first helped the band shed the alt-country tag, with Tweedy showing his diversity of songwriting styles and Jay Bennett doing his best Brian Wilson impression with his obsessive attention to detail (remember those scenes in "I Am Trying to Break Your Heart"?) resulting in an immaculately produced album. Many of Tweedy's best pop songs can be found here ("Can't Stand It," "I'm Always In Love," "Candy Floss") but some foreboding folk tunes ("She's a Jar," "How to Fight Loneliness," "Via Chicago") add a dark touch. Even the sinister songs have a warmth and brightness to them, though. This was the album where the band's creativity and confidence met at the perfect intersection, resulting in a true classic.
2. "Yankee Hotel Foxtrot" (2002) Its legend doesn't quite match its legacy, but Wilco's breakthrough album remains a mesmerizing listen. You might remember that during recording the band butted heads with then label Reprise, ended up becoming free agents, released the album on the Internet for free (this was back in 2001, mind you) and became indie cause celebres. The album signaled a new direction for the band, with pop obsessive Bennett giving way to noted Chicago producer Jim O'Rourke, who gave the album a claustrophobic, slippery feel. The drums, guitars and vocals are all very processed; it's a long way from the rugged, rustic feel of the band's first few efforts. A couple of epics ("I Am Trying to Break Your Heart," "Ashes of American Flags") are the clear standouts, but "Jesus, Etc.," "Kamera" and "War on War" are also worthy of the Wilco canon, showcasing a nuance in songcraft that wasn't previously there.
3. "Being There" (1996) Like all double albums it could certainly use some trimming, but this is Wilco delivering some of its most pleasing, straightforward rock-and-roll. The back-to-back of "Monday" and "Outtasite (Outta Mind)" is nothing but fun, which you can't really say about much of the band's later work. Twangy moments like "Forget the Flowers" and "What's the World Got In Store" don't have much depth but are enjoyable and breezy. "Being There" doesn't have the range of styles and emotions found on later albums but shows that Wilco did the roots rock thing as well as anyone.
4. "A Ghost Is Born" (2004) This was the first Wilco album that didn't feel like a new direction for the band; it was more a sequel to "Yankee Hotel Foxtrot." It's the first album without any input from original guitarist Bennett and you can certainly hear Tweedy pushing the band further away from alt-countryville on the kraut-rock influenced "Spiders (Kidsmoke)" and spacey "Hell Is Chrome." The catchiest songs ("Company In My Back" and "Theologians") are actually kind of annoying with their insistent "McCartney Bounce." The band deserves credit for mixing it up, though, and the stoned shuffle of "Handshake Drugs" makes for one of Wilco's finest moments.
5. "Sky Blue Sky" (2007) Yawn. It's one thing to retreat from the experimental tendencies that were starting to alienate some longtime fans. But I found myself longing for the hit-or-miss nature of "A Ghost Is Born" after spending some time with the agreeable-but-pretty-boring material on "Sky Blue Sky." Yacht rock, dad rock, Volkswagen rock - call it what you will, although "rock" might not be the most accurate descriptor. Guitarist Nels Cline provides many of the highlights - his nimble playing on "Impossible Germany" is particularly entrancing. But his virtuosic talents almost serve as a crutch, with the songs sort of floating along until it's time for Cline to rip off another impressive solo. It's ideal background music, but not much more.
6. "A.M." (1995) When Wilco announced its intention to play every song from its back catalog during the five-night stand in Chicago it was most surprising because that meant revisiting "A.M." in its entirety. It's not a bad album, it just has more than its share of by-the-numbers roots rock, the kind that most bands who play at Iota on Friday night could pull off reasonably well. It starts off very strong with "I Must Be High," "Casino Queen" and "Box Full of Letters," but never reaches that level again.
http://blog.washingtonpost.com/postrock/2008/02/discographically_speaking_wilc.html#comments