Following the 1994 split of the celebrated Uncle Tupelo, the betting line amongst fans and critics alike held that between Jeff Tweedy and Jay Farrar — the band’s two major principals — it was the latter headed for bigger and better things. Both songwriters had produced inspired material during the Uncle Tupelo days, but the fiercely political Farrar was the group’s undisputed leader. By comparison, Tweedy’s wry and tuneful exertions could occasionally seem a bit inconsequential alongside his cohort’s dark and rueful demeanor. Fairly or unfairly, Tweedy had been cast as “the pop guy.”

When both released albums the year following the breakup, Tweedy leading the newly formed Wilco, and Farrar fronting Son Volt, the results seemed to bear out this theory. While Wilco’s A.M. was a pleasant and varied affair with a handful of excellent tunes, Son Volt’s Trace was a stark, Springsteen-like dissertation on economic disparity and the devaluation of the working class. Trace was an undeniably powerful and unrelenting elaboration on many of the themes that Farrar had explored in his earlier material, and evidently the sound of a songwriter growing geometrically.

Not only was it the critic’s overwhelming choice, Trace also outsold A.M. handily. Wilco’s future felt fraught and uncertain as they approached the recording of their second album. Indeed, lacking a strong critical reputation or sales history, there was every reason to believe the next Wilco record might well be the last. Certainly this was not lost on the band, who put their full selves into the all-or-nothing proposition that was to follow. Then, in 1996, Being There was released and everything changed.

The remarkably diverse and energetic Being There was a double album statement of purpose and the beginning of a three-album run of masterpieces that would ultimately turn Wilco from also-rans into household names. Additionally, it yielded the first true insight into the nature of Tweedy’s genius. Its infectious combination of country, power-pop, ’70s-style boogie and Lennon-esque balladry felt panoramic and thrilling, and served also to draw a contrast between Tweedy and Farrar’s work, which, for the first time placed Tweedy in a decidedly better light.

Trace had represented a remarkable summation of Farrar’s great lyrical and musical themes, however, with subsequent Son Volt releases it became steadily clearer that these were his only themes. Unaccountably, Farrar failed to diversify and progress as a songwriter, rehashing his obsessions with an increasing tedium. Meanwhile, with Being There, Tweedy had definitively established himself as the more interesting artist going forward by dint of his nearly insouciant Catholicism toward genre and approach, which brimmed with endless possibility.

Inarguably, the key collaborative figure abetting Tweedy’s creative expansion was the late, lamented Jay Bennett, the Chicago-based multi-instrumentalist who joined Wilco, following the disbanding of his underrated Replacements-influenced outfit Titanic Love Affair. Bennett was a profoundly gifted songwriter in his own right, in addition to being a crackerjack studio hand. The chemistry between him and Tweedy over the course of the three albums they essentially produced together yielded the greatest results of Wilco’s storied run. That chemistry could also prove toxic and volatile. As former Wilco drummer Ken Coomer attests, “It was Jeff and Jay feeding off each other not just musically, but other vices. There was a bonding going on, and it didn’t just involve music. There wasn’t really a band, just two guys losing their minds in the studio.”

This chaotic dynamic was captured in spades in the 2002 documentary, I Am Trying To Break Your Heart: A Film About Wilco, which depicts two addled and brilliant lead dogs jockeying endlessly over who will ultimately be the band’s principal arbiter. When eventually, and probably inevitably, Bennett was dismissed, his loss was assuredly a creative blow.  Whereas Farrar had once served as the po-faced counterweight to Tweedy’s multifaceted genius, Bennett seems to have indulged and aided Tweedy’s every polygamous creative impulse. This was Wilco’s anything-goes period, often manifesting itself on their records as a sort of pure unrestrained id.

Being There’s follow-up, Summerteeth, the second of the Tweedy/Bennett trilogy, was at once a logical progression and also intensely perverse. Gone was nearly any vestige of country influence, replaced instead by synth-driven psychedelia that yielded tracks that were desperately personal, but sometimes nearly narcotic in their seeming remove. Summerteeth was a new and distinct take on Wilco, comprised of indelible hooks alongside excruciating moments of deep confession. Rarely have dark and light gathered so forcefully on a pop album — the combination of soaring melodies and worrying intimations of domestic abuse creates one of the more disorienting listening experiences in recent memory. All of this felt like it was leading up to some manner of culmination, but nobody could have reasonably imagined what that would be. It turned out to be the bizarre, beautiful, and psychologically fractious Yankee Hotel Foxtrot.

The final collaboration between Tweedy and Bennett remains an invaluable touchstone in early 2000s pop music and one that represents the greatest exemplar of the twosome’s troubled duality. It is a profoundly funereal record –- drugged out and longing, insular and death obsessed, searching for meaning while eerily echoing the terrified zeitgeist of its immediately post-9/11 release. Soon after, Bennett would be gone and the trajectory of Wilco would take a different course.

Tweedy and Bennett went as far as they could go together, and arguably too far. Never quite the same after his removal from the band, Jay Bennett had recently filed litigation against the group for alleged unpaid royalties before succumbing in his sleep in 2009, at the age of 45, overdosing on prescription painkillers.

Wilco post-Bennett was a different animal, and even as Tweedy pushed further into the avant-garde on the Yankee Hotel Foxtrot successor A Ghost Is Born, there was never again the sense of life-and-death stakes that had characterized Tweedy and Bennett’s epochal three-album run. Later Wilco releases have resulted in plenty of outstanding moments, many of which are mentioned below, but the overall feeling is of Tweedy pulling back from the brink, employing his remarkable talents in a less self-destructive, more reflective manner. That should be regarded as a welcome thing. Too many of our most treasured artists have taken us thrillingly close to the edge, only to topple over into oblivion. Let’s hope we have Wilco to look forward to in perpetuity.

10. “I Must Be High” (from A.M., 1995)

The lead track to Wilco’s debut A.M. is a winsome, wistful acknowledgment of the sort of romantic misjudgment that would serve as a template for many of Tweedy’s most powerful songs going forward. “I must be high/to say goodbye,” he acknowledges to a lost paramour over an infectious melody and loose band arrangement. It is a near perfect three-minute confection, hinting at the powerhouse roots rock that lies just around the corner on Being There.

9. “Jesus, Etc.” (from Yankee Hotel Foxtrot, 2002)

This minor key, mid-tempo shuffle is like a weird cousin to Antonio Carlos Jobim’s samba, filled with mysterious and surreal lyrics and one of Tweedy’s all-time greatest vocals — understated and somehow unbearably sad. “You can rely on me honey,” he pleads to a loved one, not seeming to believe it himself even for a second. The imagery is nearly Book Of Revelations scary: tall buildings shake, guitars are strung down someone’s cheekbone, each star is a setting sun. And then, eventually, a simple plea: “Our love is all we have.” A subtle song and a small miracle.

8. “Monday” (from Being There, 1996)

When the band wrote and recorded Being There, Wilco had more or less decided that this might be the end of the line, and it is near impossible to not read “Monday” as an allegory. On this stomping and infectious blowout, Tweedy channels “Choo-choo Charlie,” a journeyman musician who thinks his band is pretty damn good, and can’t make sense of the public indifference to their efforts. It is only too easy to envision Tweedy imagining this as Wilco’s future, down somewhere in Florida, driving used vans, wondering where it all went wrong. The exclamation “Get me out of TLA!” may refer to his bandmate Bennett’s former bad experience in Titanic Love Affair, or maybe just the city of Tallahassee. Neither would be wrong. Whatever the intent, “Monday” is awesome. It lies perfectly in that sweet spot between Cheap Trick power pop and Allman Brothers-style boogie, with a chorus that craves to be sung along to and a cheeriness that belies the sadness of its story.

7. “Via Chicago” (from Summerteeth, 1999)

Beginning with the couplet, “I dreamed about killing you again last night/and it felt all right to me,” “Via Chicago” is a chillingly calm murder ballad, sung with the resigned equanimity of one of Springsteen’s Nebraska characters. Strangely, despite the implied murderous streak, it is as much a tribute to Tweedy’s adopted hometown as it is a consideration of violence real or imagined. Much as Saul Bellow once did, Tweedy seems to be contemplating the city’s notorious killing floors for stock animals, and the resultant river of blood, as he sings with fear and anticipation: “I’m coming home/via Chicago.” He might not like the impulses it inspires in him, but he knows it’s the only place he can truly be home.

6. “Hate It Here” (from Sky Blue Sky, 2007)

The best track from their 2007 release Sky Blue Sky finds Tweedy and company experimenting with a neo-soul sound someplace between Carole King’s “No Easy Way Down” and the best of the Billy Preston-backed Beatles. The loose interplay between organ, piano, and lead guitar complements Tweedy’s domestic pleas (“What am I going to do when I run out of shirts to fold?/What am I going to do when I run out of lawn to mow?”). Even advertising himself as bridled and housebroken, Tweedy’s vocals have never sounded more rough and ready, giving this the feel of a winning outtake from Dylan’s I’m-just-a-guy-at-home classic New Morning.

5. “At Least That’s What You Said” (from A Ghost Is Born, 2004)

Amongst the most daring and singular songs in the Wilco catalog, “At Least That’s What You Said” is the first track on the follow-up to their most notable success, Yankee Hotel Foxtrot. It is also a conscious shot across the bow, suggesting that newly minted NPR listeners should expect a bumpy ride before making easy accommodation with their new favorite band. The 5:33 opus is comprised of two verses, followed by a “Cortez The Killer”-style guitar outro that runs the gamut from lyrical to migraine-inducing. As reactions to sudden fame go, this ranks as one of history’s least compromised.

4. “Dawned On Me” (from The Whole Love, 2011)

“Dawned On Me” is a high point of later-period Wilco, combining squalling feedback, an inescapable melody line, and a tricky key change, all of which demonstrate Tweedy at the top of his craft. As a narrator, he reminds us only too capably of his ecstatic highs and lows. “I can’t help it if I fall in love with you again,” he sings, and there is little way of knowing if this portends good things or the apocalypse. Regardless, this is amongst the best pop songs in Wilco’s catalog.

3. “Nothing’severgonnastandinmyway (again)” (from Summerteeth, 1999)

While Summerteeth contains a number of beautiful and frightening songs of domestic dissolution like “She’s A Jar” and “Via Chicago,” there is also a sense that even while he is at the end of his rope, Tweedy is still valiantly attempting to put all the pieces back together. Amidst no shortage of bleakness, the infectious “Nothing’severgonnastandinmyway (again)” emerges, a lovely pop gem with a gorgeous vocal line, including soaring backing vocals and stunning harmonies from Jay Bennett. Perhaps the most moving element of the song is the apparent self-delusion of its major claim. All available evidence suggests that either Tweedy or the song’s fictional narrator is in a miserable bind, and everything for the foreseeable future is going to stand in his way again (and again). It is hope against hope, set to a Beach Boys melody, becoming ever more poignant as it appears ever less credible.

2. “Ashes Of American Flags” (from Yankee Hotel Foxtrot, 2002)

The emotional apex of Yankee Hotel Foxtrot is one of the truly transcendent moments in recent pop music history. Here, perhaps for the first time, Tweedy seems to have fully inculcated his wide range of influences from D. Boon to Woody Guthrie and distilled them into something utterly unique. On one of his best ever set of lyrics, he begins by bringing weight to the utterly prosaic, describing his entirely normal surroundings with an odd wonderment. “The cash machine/is blue and green,” he sings as the song lopes toward whatever strange and beautiful catastrophe it is irrevocably headed to. The intensely peculiar sense of disconnect and longing, of senses both heightened and numbed, is both fatiguing and weirdly uplifting. Over a slow-building beat, he muses: “I wonder why we listen to poets, when nobody gives a fuck?” Then he answers his own question with a timeless epigram of personal confession: “All my lies are only wishes.” That’s why we listen, and that’s why we give a fuck.

1. “Misunderstood” (from Being There, 1996)

“Misunderstood” was the great transitional piece that at once freed Wilco from the prison of “alt-country” and also signaled that further expectations should be approached with caution. It is a brilliant, slow-burning track that exists someplace between the yearning of the Replacements’ “Unsatisfied” and the hope-for-the-best, plan-for-the-worst mood storm of John Lennon’s Plastic Ono Band. Tweedy’s voice sounds weathered and weary as he catalogues the alienating indignities that often accompany the existential realization that so much of life is dull and disappointing. By the outro, he has worked himself into a sort of tongue-in-cheek catharsis, screaming, “I’d like to thank you for nothing at all.” It is the perfect end of the beginning.

Listen to our countdown playlist on Spotify here.

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Comments (158)
  1. Hidden due to low comment rating. Click here to see

  2. I Am Trying To Break Your Heart doesn’t even make the top ten!? So long Stereogum, it’s been a blast!

    • For real. Stereogum, you confuse me.

    • I hate how most lists in websites (not just specifically stereogum), try not to make the ‘mistake’ of including the bands/person’s most popular work, no matter how good it is.
      It’s like Stereogum is trying to break my heart

    • Spot on. And no “Handshake Drugs” or “Shot in the Arm”?


      • Yeah, the omission of “Handshake Drugs” and “I Am Trying to Break Your Heart” is ridiculous. But so “Pot Kettle Black” and “ELT” and “One Wing” and the list goes on and on. I couldn’t even attempt to name my top 10 favorite Wilco song so I commend the valiant effort.

        But seriously, “Handshake Drugs” is top 5 for sure.

      • yes! “handshake drugs” and “shot in the arm” should both be in the top ten. and “i am trying to break your heart” should be there, too. the further i went down the list, i just kept waiting for them to show up… at least “jesus, etc.” and “via chicago” are in there.

    • I can obviously go on about all the songs that should’ve been on this list, but it looks like that is being taken care of. The fact that there can be SO MANY different possible top-10 Wilco songs for so many different people only speaks to the band’s sheer fucking genius catalog.

  3. Pretty solid list, I’d just like to submit for your approval that “I Am Trying to Break Your Heart” is not only Wilco’s best song, but one of the best songs of the last decade. Two cents.

  4. Is this an NME list?

  5. I acknowledge that narrowing their catalog down to the best 10 songs is a near-impossible task..and I commend you for taking it on… but “I Am Trying to Break Your Heart” should be somewhere on here.

  6. “Stereogum turned into a click-baiting, listicle site so gradually, I didn’t even notice.”

  7. Props for Ashes of American Flags at #2, and for not including I’m Always In Love just cus it’s been played out by that commercial.

  8. Id have to pick ‘radio cure’ for my favourite tune, for some reason that song gives me the chills no matter how many times i listen to it

  9. also its very hard to ignore those 6 or so amazing songs they’ve developed based on lyrics/poems/words from woody guthrie.

    oh and sunken treasure…. this is simply a terrible list

  10. Forget the Flowers Doooooood

  11. Jesus, Etc. = #1

  12. I’m sorry but this list is wrong. It’s missing Impossible Germany.

  13. So many to choose from to get it down to 10 BUT to choose I MUST BE HIGH and MONDAY??!
    Those shouldn’t even be on the top 50 list.

  14. She’s a Jar. Best Wilco Song Ever. Period.

  15. Because I so thoroughly agree with your pick for #1 I’m going to go along here, but I’m not that happy about it…

  16. Minus the inclusion of anything post YHF – I am so glad to finally read an article about Wilco by someone who gets it. Wilco is Being There, Summerteeth, and Yankee Hotel, Wilco is Tweedy and Bennet. Anything else is a joke, a sorry excuse, and frankly, should be called something else.

  17. Ballsy list guys (if a list can even be that), I approve.

  18. HATE IT HERE?? And not say, A Shot In the Arm or Handshake Drugs??? It seems like you are just looking for a fight here.

  19. I feel like if you’re taking a song from Sky Blue Sky it pretty much has to be “Impossible Germany,” right? I can get behind a few of these choices, but I’m not even sure “nothing’severgonnastandinmyway” is one of the top 10 songs on Summerteeth… “I’m also in the “I Am Trying to Break Your Heart” camp here. Oh fuck it here’s the list I would have made:

    1. Via Chicago
    2. Poor Places
    3. Misunderstood
    4. Handshake Drugs
    5. Jesus Etc.
    6. I Am Trying to Break Your Heart
    7. Impossible Germany
    8. Shot in the Arm
    9. Sunken Treasure
    10. One Sunday Morning

  20. WHOA WHOA WHOA – i can agree with only 2 nods to anything post-YFH, but the exclusion of “i am trying to break your heart” is criminal indeed

    i’ve been wanting to get validation in my derision with these “lists” for awhile now – now i’ve doubtlessly found it

  21. A Shot in the Arm is easily a top 5 Wilco song (if not top 3). And A Ghost is Born is vastly underrated.

  22. Glad to read an article by someone who gets it. Wilco was Jeff and Jay. Anything else should be called something else.

  23. A lot of misses, but really, how can you leave off “I Am Trying to Break Your Heart” and “Impossible Germany?”
    Alas, this list was never going to be perfect, and it would never please a majority, but some of these picks are straight up weird.

  24. Lots of um, different choices on here. I’d submit this list:

    I Am Trying To Break Your Heart
    Shot In The Arm
    Outtasite (Outta Mind)
    Impossible Germany
    War on War
    Sunken Treasure
    Via Chicago
    Jesus Etc
    Poor Places
    One Sunday Morning

  25. Heavy Metal Drummer?

  26. 2 disc set:

    I Am Trying to Break Your Heart
    Art of Almost
    Via Chicago
    Heavy Metal Drummer
    Spiders (Kidsmoke)
    You Are My Face
    War on War
    Muzzle of Bees
    California Stars

    At Least That’s What You Said
    Jesus Etc
    I Might
    Handshake Drugs
    Can’t Stand It
    Bull Black Nova
    Company in My Back
    Pot Kettle Black
    Shot in the Arm
    One Sunday Morning

  27. I think Misunderstood is a pretty good choice, but am I the only one who despises Dawned on Me?

  28. Am I the only one who loves Candyfloss?

  29. Hidden due to low comment rating. Click here to see

  30. I haven’t seen some of Wilco’s great title tracks mentioned. Sky Blue Sky and Summerteeth have always been favs of mine. Wilco(the song) is great too but not sure if that counts.

  31. Couldn’t we just consider Yankee Hotel Foxtrot one BIG song and put a #1 on it?

  32. I’m sorry but “Hate It Here” may very well be the worst song Jeff Tweedy has ever written. It is absolutely terrible. And I love Wilco with my whole heart.

  33. From the get go you could tell the author was going to put more early Wilco on the list. He pretty much come out and says “I think Being There is as good as Yankee Hotel Foxtrot.”
    My three cents would be:
    Heavy Metal Drummer
    Capital City
    Either Way (most underrated Wilco song)

  34. They definitely got it right with misunderstood. I really liked this list of their top 5 best albums:


  35. Can we call these lists something like “10 Songs That Sum Up Wilco’s Greatness” or something like that?

    These lists are never the band’s 10 single best songs. Because when we’re talking about a great artist/band with a fairly large catalog, there’s no such thing as the 10 best songs. You can rank albums, sure, but not songs. There are too many great ones and too much variation among them, so it becomes an apples and oranges kind of thing.

    This is also why some of you commentators need to quit having a hissy fit when one of your favorite songs isn’t picked. When we’re dealing with catalog such as Wilco’s which contains so many amazing songs, it is inevitable that one of your favorites won’t get picked.

  36. honestly, about half of my list would be tracks from a ghost is born.

  37. Does California Stars count? Because it should.

  38. “Impossible Germany” should be the only track from SBS on this list. And at #1.

  39. Misunderstood
    At Least That’s What You Said
    I’m Always In Love
    Ashes of American Flags
    Red-Eyed & Blue/I Got You
    Pieholden Suite
    I Am Trying to Break Your Heart
    Poor Places
    Cars Can’t Escape
    Shakin Sugar (Alone)

  40. 10. The Late Greats
    9. The Lonely 1
    8. Impossible Germany
    7. Via Chicago
    6. Spiders (Kidsmoke)
    5. How To Fight Loneliness
    4. Misunderstood
    3. I Am Trying To Break Your Heart
    2. Art Of Almost
    1. Poor Places

    This is my list now, but I’m sure I’ll be kicking myself later for forgetting something.

  41. i submit “i’m always in love” for your approval, grand stereogum council.

  42. As a long time Wilco fan (started listening to UT through the No Alternative compilation), this list has several problematic inclusions. Opinions are opinions of course, but “Nothingsevergonna…” and “Hate It Here” are in no way among the Top 10 Wilco songs. As one commentor said earlier, “Nothings..” not even in the Top 10 on Summerteeth. And “Hate it Here” is just seriously the pits – one of the most annoying and pandering songs Tweedy’e ever written.

    That being said, bravo for “At Least That’s What You Said”, a personal fave. Also, I appreciate how you try to include something from all eras of the band. I guess “I Must Be High” is a good choice from AM, but “Box Full of Letters” to me is the better song. Also, “Monday”, while a fun, Stonesy-rocker, is not as good as “Far Far Away”, “Outtasite”, “Sunken Treasure”, “Red Eyed and Blue” and a couple of other Being There songs.

    A lot of commentors are crying foul over the exclusion of “I Am Trying to Break Yr Heart”, but I’d agree that “Ashes” is a better choice from YHF, as would be “Poor Places”, “War on War”, “Reservations”, or “Kamera”. Maybe a few others too.

    In addition to what I’ve already mentioned, off the top of my head their best tracks are:

    Passenger Side
    Can’t Stand It
    Shot in the Arm
    Hell is Chrome
    Handshake Drugs
    Pot Kettle Black
    I’m Always in Love
    Not for the Season (Laminated Cat)
    Wishful Thinking
    Impossible Germany

    A top 10 is pretty hard for such a great band. Nice try though.

    • The stereogum list is absolutely bonkers. But so are most of all the commenters list. I am Trying To Break Your Heart shouldn’t be anywhere near a top ten wilco song list. And How has only one person mentioned Wishful Thinking, which is easily their best one. The list should look something much closer to this one.

      1) Wishful Thinking
      2) Jesus ETC
      3) Poor Places
      4) Pot Kettle Black
      5) Say You Miss Me
      6) She’s A Jar
      7) Ashes Of American Flags
      8) Impossible Germany
      9) Muzzle Of Bees
      10) Hotel Arizona

  43. “Muzzle of Bees” and “Poor Places” top my list.

  44. I like post-YHF Wilco. Fuck me, right?

  45. For fucks sake Stereogum.

  46. I don’t think these Stereogum articles are supposed to present some sort of definitive list, but rather just get a conversation going. My list looks something like this:

    1. Jesus, Etc.
    2. Via Chicago
    3. Misunderstood
    4. I’m Always in Love
    5. One Sunday Morning (Song For Jane Smiley’s Boyfriend)
    6. Outtasite (Outta Mind)
    7. Kamera
    8. ELT
    9. Can’t Stand It
    10. Impossible Germany

  47. Hard not to weigh in on a Best of Wilco list.

    I’m not saying these are the best songs, but I think they deserve more recognition than what they’ve received so far in this post/comment thread:

    Can’t Stand It (Summerteeth)
    Hell is Chrome,The Late Greats, Muzzle of Bees, Company In My Back (A Ghost is Born)
    Bull Black Nova, Everlasting (Wilco (the Album))
    You Are My Face (Sky Blue Sky)

    • Kudos for the mention of Bull Black Nova. Sure, few people would argue that Wilco (the Album) is their best LP (many may argue that it’s their worst), but Bull Black Nova is a great song. It’d be a real contender for my top 10 list.

  48. “What am I gonna do when I run out of lists to make?”

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