I'm taking the bait and re-doing Wilco. I've been listening them voraciously for the past year and are one of the few discographies I know, so I hope y'all enjoy. Excuse any poor grammar and stuff.
Wilco was born from the remnants of Uncle Tupelo, who were the center of the roots rock/alt-country explosion in the 1990s. Uncle Tupelo was led by Jay Farrar and Jeff Tweedy, who shared songwriting duties and were longtime friends. They released 4 amazing albums and then imploded in 1994, with Jay Farrar creating Sun Volt and Jeff Tweedy creating Wilco. The music industry had always seen Jay Farrar as the stronger of the duo, and expected much bigger things from Son Volt then Wilco. They weren't really right.
Released roughly around Son Volt's Trace, A.M reinforced the general purview of Uncle Tupelo post-breakup: Jay Farrar was the tortured genius, Jeff Tweedy was the serviceable songsmith. The record closely follows its alt-country base, sounding in large part like an Uncle Tupelo album. This doesn't mean it's a poor album, it just really doesn't do anything new or groundbreaking. This is an album for the completionist Wilco fans and isn't that essential.
Best Songs: Casino Queen, Box Full of Letters
Being There (1996)
This is Wilco's "Big Leap Forward." Unlike A.M, which used country-rock as a location to play within, Being There used it as a jumping off point, incorporating psychedelica, blues and straight up rock to create a brand new sound that both defines Wilco to this day but defies any real label. The songwriting also vastly improves on Being There, containing some of Tweedy's best lyrics, including perhaps my favorite opening line: "You're back in your old neighborhood / The cigarettes taste so good / But you're so misunderstood." This album asserted Wilco's place in the alt-country scene (perhaps even at its peak) and generally ended any Son Volt/Wilco debates. Unfortunately, the second disc bloats the album a bit, but the first disc really doesn't have a weak song. This is the album to start if you're already into alt-country/country and want to get started on Wilco.
Best Songs: Misunderstood, I Got You (At The End Of The Century), Monday
Wilco and Jeff Tweedy took a bit longer with Summerteeth, but the time away show a new maturity in Wilco's sound. With Summerteeth, Tweedy and co. strip away the fat of their previous albums and ditch many of their alt-country cobwebs, expanding into a pop sound characterized by beautiful arrangements and more encompassing influences, from R&B to psychedelica. By this point, its pretty pointless to call Wilco an alt-country band, and they essentially move outside of genres, becoming, at least in my opinion, to be simply an American band. The songwriting on this album also steps up, delivering some of Tweedy's darkest lyrics, even among the relative sunshine and pop of the album itself. It's a really hard thing to describe this album, but I honestly think it's one of the most American things there is. Start here if you just want a jumping off point. It's brilliantly conceived pop/rock.
Best Songs: Can't Stand It, A Shot in the Arm, Via Chicago
Yankee Hotel Foxtrot (2002)
There's a reason this is generally considered one of the greatest albums of the 2000s. Taking the experimental undertones of their previous two albums and the ever-improving songwriting of Jeff Tweedy, YHF is a masterpiece of soundscapes, Americana and beautiful melodies. The album starts much like Being There, with a wall of noise, but this explosion of sound makes Being There sound childish. Incorporating field recordings, noise, and production as a tool for expanding the emotional weight of Tweedy's lyrics, I Am Trying to Break Your Heart is easily one of Wilco's best songs and sets a clean table for YHF to expand upon. From IATTBYH, Jeff Tweedy wraps the rest of the album in both experimental undertones and warm acoustics, juxtaposing and revealing each in their own relative corners, sometimes simultaneously and other times starkly alone, creating a real sense of both warm insularity and cold reality. A lot has been said about this album's relevance post-9/11, and while the direct ties are a bit of a stretch, I feel like this album really does characterize the modern psyche of the American people in its relative assertion of alienation, fear, nostalgia and hope as simultaneous feelings within our day to day life. OK Computer and Kid A are generally noted as the greatest representations of the modern psyche, but I really do think YHF stands right next to them. It's honestly a masterpiece. I wouldn't make it your first listen, but you really can't go wrong with YHF. If anything, it just might take a while to click.
Best Songs: Side A, Side B - There is not a weak track on this album.
A Ghost is Born (2004)
The best summary I've found for A Ghost is Born is that it's a re-tread of YHF with the warmness of Summerteeth. It contains much of the experimental side of YHF but without its distance and somber tone, instead favoring the openness and organic honesty that informs Summerteeth. This album has some of Wilco's poppiest songs, but also their most experimental, creating an interestingly catchy mix of YHF and Summerteeth that puts it as one of their most fun records once you get past some of the too-dense stuff. However this density sometimes overpowers the album, dragging down the simple joy of songs like Hummingbird and The Late Greats, but in all honesty, this album is an earworm of art-pop and rock. This was the last Wilco album I heard, but its also one of my favorites. As such, give it a listen if you like Wilco's experimental stuff.
Best Songs: Spiders (Kidsmoke), Hummingbird, I'm A Wheel
Sky Blue Sky (2007)
Wilco partly returns to Being There and their alt-country roots with Sky Blue Sky, but rather than a step backwards, it feels like a necessary reconciling and needed break in their discography. The run of Summerteeth to A Ghost is Born was astounding in its heights, but exhausting in its brilliance and leaps forward, and so Sky Blue Sky really feels like a pleasant interlude and reorganization of Tweedy's head. The darkness is still there in the songwriting, as is the experimental side, but there's a renewed focus on the roots rock and open spaces the characterized Wilco's earlier work. It also has some of Wilco's best guitar lines, delivered by the gifted Nels Cline, and some wonderful keyboards courtesy of Pat Sansone. There's also a few new avenues of sound that keep the record from being a total retread, with the pleasant soul sound of Side with the Seeds and the boogie-woogie rock of Hate it Here. It's mellow and comes across initially as a bit of a snoozer, but it definitely grows into one of Wilco's best. Grab this album whenever, you'll probably enjoy it as a hardcore fan or a total acolyte.
Best Songs: Either Way, Hate it Here, Walken
Wilco (The Album) (2009)
Now 6 albums in, and Wilco is firmly in their groove, for better or worse. This albums continues down the path of Sky Blue Sky as wholly enjoyable, taking the best of Wilco and smushing it all together, but it really doesn't do anything new or as ambitious as before. Not to say the album is boring, but while Sky Blue Sky is a pleasant interlude, Wilco (The Album) starts to sound like a band that doesn't plan on going anywhere anytime soon. Which is a bit scary, seeing as they essentially created some of the best music of the 1990s and 2000s, but with songs as fun as Wilco (The Song) and as forward as Bull Black Nova, it's hard to really fault them. This isn't an important Wilco album, but its enjoyable nevertheless, I'd get it once you start running out of the important ones to digest.
Best Songs: Wilco (The Song), Bull Black Nova, You Never Know
The Whole Love (2011)
Whatever worries Wilco engendered with Wilco (The Album) essentially dissolve with The Whole Love. This album achieves the blend of Wilco elements that characterized Sky Blue Sky and Wilco (The Album) while staying far away from any real retreads or worries of stagnation. Starting with Art of Almost, Tweedy reasserts the experimental bravado of A Ghost is Born and YHF with a pulsating intro that explodes into one of Wilco's most pummeling songs, reminding everyone that the experimental rock is still plenty alive in Tweedy's head. Similarly, the poppier tracks on The Whole Love rank with Wilco's best, taking familiar sounds and adding a bit of spice or stretching their ideas a little bit further than before. Furthermore, The Whole Love demonstrates the "band" of Wilco much more so than their other albums, with a interplay of instruments and ideas that indicate that there is plenty left in the pot for Wilco. This was one of my favorites of 2011 and has got me excited again about where Wilco is going as a band. While it's not quite as great as ST/YHF/AGIB, I don't think there's any problem starting with this album or adding it to your rotation at any time.
Best Songs: Art of Almost, Dawned on Me, Standing O
7. Wilco (The Album)
6. Sky Blue Sky
4. Being There (tie)
4. The Whole Love (tie)
3. A Ghost is Born
1. Yankee Hotel Foxtrot
Where Do I Start? (TL;DR):
I'd start with Summerteeth then YHF. From there, explore Being There and Whole Love. After that you should have a good enough grasp on Wilco to figure things out on your own. Enjoy the ride!
Where Do I Go Next?:
If you like Jeff Tweedy's voice and acoustic work, definitely grab some of his work with Billy Bragg on old Woody Guthrie songs. The three albums they recorded, Mermaid Avenue Vol 1-3, have some of Wilco's best material and some of their most boring. It's worth digging through though, and if you like Billy Bragg, give him a listen too.
As for similar bands, I'm not as knowledgeable, but I have heard good things about Jay Bennet, who worked with Tweedy from Being There to YHF (partly) and who's album The Magnificent Defeat garnered good reviews. So that's worth a shot.
If you're into the more alt-country stuff, listen to Son Volt and Uncle Tupelo, they're both wonderful and I think are a rather good jumping off point for alt-country in general. You can't go wrong with either of their first albums.
But that's about all I know.
We did it! That's Wilco!