The 10 Best Wilco Songs of All Time

Wilco, perhaps more than any alternative rock band of the past couple years, has taken its listeners on a wild, unexpected journey through a confluence of diverse musical styles. From its earliest days as an offshoot of alt-country pioneers Uncle Tupelo, to its dabbling with influences from noise rock, Krautrock, orchestra pop, and experimental jazz, to the folksy, simple songs from more recent albums earning the group the derogatory label “daddy rock”, Jeff Tweedy and company are always full of surprises. The band’s lineup has changed frequently and reveals a group constantly pushing itself into uncharted musical territory.

The journey began with A.M., the band’s 1995 debut record, which retained much of the group’’s alt-country roots. With Being There (1996), Wilco’s experimental side was already showing on such tracks as “Misunderstood” and “Sunken Treasure”, though classic rock and roots music were still obvious influences. On Summerteeth (1999) the group expanded its sound exponentially. It was clear that the band members, especially guitarist/keyboardist Jay Bennett, had fallen under the spell of Brian Wilson-style orchestral pop. String sections, unconventional percussion, and complex keyboard songs peppered this collection of pop songs.

With 2002’s Yankee Hotel Foxtrot, Wilco went from being a solid, much admired alternative band to a musical and artistic institution. Critics recognized Yankee as not just an innovative musical effort, but one that was inflected with cultural significance. Jeff Tweedy’s unique songwriting voice came to the fore, with some venerating him on the level of Bob Dylan and Neil Young. While Yankee had its unconventional moments, A Ghost Is Born (2004) represents the band’s most all-out experimental effort. Tracks like “At Least That’s What You Said” and “Spiders (Kidsmoke)” approach atonality, but the 15-minute “Less Than You Think” — consisting of a short acoustic melody followed by several minutes of high-pitched, non-melodic sonic patterns — tried the patience of even Wilco’s most progressive fans.

On Sky Blue Sky (2007), though, Wilco went in the complete opposite direction. Gone were the non-tonal experiments, complex rhythms, and layers of challenging guitar parts. Instead, the band released an album of simple, piano-driven ballads and gentle, straight-ahead rock tunes. The group’s seventh studio album, Wilco (The Album) (2009), represented a blended approach, with influences from each era of the band’s development thrown into the melting pot.

With the upcoming September 27th release of the The Whole Love, the band’s eighth studio record, it’s worth going back and revisiting the group’s impressive discography. As I compiled this list of the top ten Wilco songs, it became obvious to me that, unlike many artists, there are very few clear “singles” or “hits” to highlight. Because Wilco has never really been a “radio band”, I simply tried to pick the ten songs that I feel the deepest connection with. Since Wilco is such a musically varied ensemble, everyone’s experience of the group is likely to be different. While these ten songs represent a good starting point for the uninitiated, I would be remiss if I didn’t recommend listening to the band’s entire catalog as often as possible.

10. “Far, Far Away”
from Being There

Wilco is a quintessential Chicago band. In “Far, Far Away”, one gets the feeling of riding the L train on a foggy autumn night. The gently lilting groove, folksy harmonica, and soulful pedal steel all add up to one of the band’s most effective tunes about love, longing, and the emotional and physical distances that can plague even our most meaningful relationships. As it evokes feelings of alienation, “Far, Far Away” anticipates the themes and melancholy moods of Yankee Hotel Foxtrot. At the same time, though, it reflects the band’s alt-country roots. The honesty of the lyrics and the emotional expression of Tweedy’s voice leads to one of the simplest, yet warmly effective, tracks in the band’s varied catalog.

9. “Spiders (Kidsmoke)”
from A Ghost Is Born

It’s hard to believe that “Spiders (Kidsmoke)” was recorded by the same band that gave us “Far, Far Away”. The directly emotional lyrics (“I need to see you tonight”) are replaced by surrealistic, symbol-laden lines (“This recent rash of kidsmoke / All these telescopic poems / It’s good to be alone”). The country-inflected rhythms and sparse instrumentation are replaced with walls of free jazz-influenced guitar noise and Krautrock-inspired grooves. One of the most divisive tracks on A Ghost is Born, “Spiders (Kidsmoke)” represents what many find so simultaneously fascinating and frustrating about the group. If you’re willing to take the journey, though, Tweedy and company prove on this ten-minute track that their often derogatory label of “daddy rock” is far too limiting.

8. “Poor Places”
from Yankee Hotel Foxtrot

“Poor Places” is notorious for its inclusion of samples from The Conet Project, recordings of number stations that were odd shortwave radio signals of undetectable origins. The use of the phrase “Yankee, Hotel, Foxtrot” from the number stations on the album’s penultimate song emphasizes the feeling of emotional alienation expressed on the entire record. “Poor Places” explores the ways in which, even in a world as “connected” as our own via technology and mass transportation, we can feel remarkably disconnected from one another. The speaker suggests that he only finds himself caring about what is happening immediately around him (“It makes no difference to me / How they cried all over overseas / If it’s hot in the poor places tonight / I’m not going outside”). The presence of a line as concrete as “I really want to see you tonight” amongst a sea of semi-abstract lyrics suggests the optimistic belief that love can overcome the danger of growing apart in our complex world.

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7. “Handshake Drugs”
from A Ghost Is Born

“Handshake Drugs” begins with the rather insipid lyric “I was chewing gum for something to do.” The boredom inherent in the opening line, though, kicks off an adventure involving saxophones that blow the speaker down, continually moving taxi cabs, and the eponymous “handshake drugs”, which might represent Jeff Tweedy’s migraine medication, the unrequited handshakes of fawning fans, or, you know, literally the kind of drugs you might buy downtown. Nevertheless, the track is notable for its steady, strut-like groove juxtaposed with noisy, experimental guitar layers. It also seems to come from a starkly honest place. By the end of the song, the speaker is repeating the line “It’s OK for you to say what you want from me / I believe that’s the only way for me to be exactly what you want me to be.” Whatever the meaning of the song’s “handshake drugs”, this tune is clearly about trying to be someone you are not for the sake of another. The sense of exasperation in Tweedy’s voice seems painfully real.

6. “At Least That’s What You Said”
from A Ghost Is Born

“At Least That’s What We Said” kicks off A Ghost Is Born with a whimper, not a bang. The song’s brief lyrical section realistically depicts a relationship suffering from a lack of communication (“Maybe if I leave you’ll want me to come back home / Maybe all you mean is leave me alone / At least that’s what you said”). This opening track, though, quickly establishes the fact that A Ghost Is Born is about musical more than lyrical innovation. After the brief opening lyrics, Wilco embarks on a journey that in lesser hands could come off as jam band pretension. Jeff Tweedy’s tortured guitar solo is purportedly an audio representation of the pain he feels during the migraine spells he suffers from. In the context of the song, though, it sounds more like the violent emotions building up inside the hearts of uncommunicative lovers, ready to come brimming to the surface.

5. “I Am Trying to Break Your Heart”
from Yankee Hotel Foxtrot

By now, it’s pretty much a critical cliché to point out the fact that Yankee Hotel Foxtrot, a record thought to reflect America’s downtrodden mood and unique obsessions following the September 11, 2001 terrorist attacks, begins with the line “I am an American”. “I Am Trying to Break Your Heart”, though, isn’t so much about the anxieties of an entire nation as the insecurities of the song’s drunken, jaded protagonist. Lines with such clarity as “What was I thinking when I let go of you” and “You were so right when you said I’ve been drinking” are juxtaposed with the surrealism of “let’s forget about the tongue-tied lightning” and “take off your band-aid ‘cause I don’t believe in touchdowns”. The song seems to be about a semi-delusional man trying to reconnect with a former lover on a drink-filled night. Thematically, it establishes the feelings of emotional and lyrical distance that will haunt the entire record. Musically, the song’s layers of diverse, often random, sounds cement the fact that this will be a sonically challenging, yet endlessly fascinated album.

4. “Misunderstood”
from Kicking Television

It often takes bands several albums to start getting all “meta” and reflecting on the nature of their own existence as a musical unit. It only took Tweedy two records, though. “Misunderstood” is the opener from the band’s sophomore effort “Being There,” although I’ve included the version from the live record Kicking Television here because it has become one of the most exciting parts of the band’s live sets. “Misunderstood” tells the story of a musician who returns to his former hometown only to find that he is not as appreciated or “understood” by his former friends as he would have liked. Lines like “You think you’ll just climb back in bed / With a fortune inside your head” suggest that the musician has much more potential than he is actually utilizing, a message rendered powerful by a band in the early stages of their career. The song’s repeated final line of “I’d like to thank you all for nothing at all” can be read as the song’s protagonist talking to his former friends, Tweedy ironically talking to his audience, or both. Tweedy is known to repeat this line with an obsessively feverish emotional intensity for minutes at a time at Wilco’s live shows.

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3. “Via Chicago”
from Summerteeth

Given the debate about violent imagery in rap music fueled by Los Angeles collective Odd Future Wolfgang Kill Them All, it’s worth remembering that other musical genres can equally explore the dark side of human existence. “Via Chicago” starts with these strikingly provocative lines: “I dreamed about killing you again last night / And it felt alright to me.” The song continues with such stark imagery as “Your cold, hot blood ran away from me to the sea.” “Via Chicago” is one of the most beautiful paradoxes in Wilco’s songbook, a track simultaneously about the mixed feelings we may have about someone we love, the power of love to transcend the pains of death, and what it means to search for a home. Musically, “Via Chicago” finds a delicate balance between the band’s folky, acoustic side and its experimental tendencies. The first half of the song is relatively straight ahead, but the second features an arhythmical drum “freakout” and a collage of atonal guitars. The palpable pain in Tweedy’s voice as he repeats the line “searching for a home via Chicago” at the end of the song suggests the anguish of a vulnerable, confused man.

2. “Ashes of American Flags”
from Yankee Hotel Foxtrot

Yankee Hotel Foxtrot‘s release date was originally slated for September 11, 2001. However, because of record company complications detailed in the documentary I Am Trying to Break Your Heart: A Film About Wilco, the album’s official release date was pushed back. When the tracks leaked online, though, the band started streaming the album a few days later. In the shadow of the September 11 attacks, many found solace in the record’s evocation of themes of alienation and its overall melancholy tone. The provocatively titled “Ashes of American Flags” especially speaks to the feelings of helplessness many experienced in the wake of the tragedy. The song describes a world in which the best way to spend money is on Diet Coke and unlit cigarettes, nobody appreciates the profound wisdom of poets, and the ultimate sign of success is experiencing “a fresh wind and bright skies to enjoy my sufferings”. The speaker realizes that his perusal of the American Dream is leaving him short of legitimate happiness. His “lies are always wishes”. The song’s final two lines (“I would like to salute the ashes of American flags / And all the falling leaves filling up shopping bags”) simultaneously suggest despair and optimism. The American flag, a symbol whose power became especially potent following the attacks, might have fallen to ashes and the dying leaves might be falling off of the trees. However, the trees will one day grow their leaves back and the flags will one day represent something meaningful for the speaker. The cycle of life is apparent, even amongst the speaker’s despondency.

1. “Radio Cure”
from Yankee Hotel Foxtrot

“Radio Cure” begins with one of the most emotionally naked lines from Yankee Hotel Foxtrot: “Cheer up honey, I hope you can / There is something wrong with me.” Appropriately, the musical texture at the start of this track is as sparse as it has been on the record thus far, a minimalist acoustic guitar part consisting of one prominently repeated note layered on top of a quarter-note bass drum pattern. They key word in this opening lyric, though, is “something”. Is the speaker referring to a physical ailment, the emotional scars of a failed relationship, or both? Some have interpreted the song as being about a cancer victim, with lines about “radio cures” and “electronic surgical words”. More than likely, though, the speaker is reflecting on the pains of lost love. His mind is filled with “Silvery stars / Honey kisses clouds of love” because he can’t erase the blissful memories. The famous line “Distance has no way of making love understandable” suggests that no matter how much he tries to separate himself from the memory of his former lover, he will never fully recover. “Radio Cure” is simultaneously one of the greatest breakup songs of all time and a stirring metaphysical reflection on the fragility of existence.