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.