The 30 Best Wilco Songs

From A.M. to Schmilco, and everything in between.

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20. “Heavy Metal Drummer”
The nuance of “Heavy Metal Drummer” is what separated Wilco from the acceptable norm of alternative bands in the early-‘00s. The whimsy of an orchestra fading out from “Ashes of American Flags” ( to the opening beats of “Heavy Metal Drummer” seemingly separate from the entirety of the song) was both brilliant and divisive, and the documentary I Am Trying To Break Your Heart depicts Tweedy and Jay Bennett famously hashing out this kind of minutia. It probably contributed to Bennett leaving the band and Reprise/Warner dropping them, but Tweedy’s distinct vision for Yankee Hotel Foxtrot ultimately won. And he was right about it all, too. Caring about a weird out-of-place intro that became the hallmark for a song about teenage summertime nostalgia—bathed in flowers and psychedelic synths—is what made this song great and Wilco who they are. —Adrian Spinelli

19. “Ashes of American Flags”
Both the title track of a DVD of the same name and a song from Wilco’s breakthrough album Yankee Hotel Foxtrot, “Ashes of American Flags” is delivered with a blend of remorse and reflection, a stark reminder of the fact that for all that’s promised, all that’s hopeful, it mostly seems like shattered dreams when we’re at our lowest. Tweedy wonders, “I’m a hole without a key if I break my tongue / Oh, speaking of tomorrow, how will it ever come?” Both beautiful and heartbreaking all at the same time, it ranks among Wilco’s most forlorn melodies, and their most restive as well. —Lee Zimmerman

18. “War on War”
When Paste Magazine launched in 2002, the CD sampler for Issue #1 kicked off first with a simple acoustic guitar strum in the right speaker, then both speakers, then a high-pitched electric guitar lick followed by what sounded like the echo of muted alarm from some nuclear submarine and ultimately a fuzzy wah-wah alien siren. We chose “War on War” as Track 1 to launch what we hoped would be a different kind of music magazine because this was a different kind of music. I still don’t know what “You are not my typewriter / But you could be my demon / Floating through flaming doors” means, but I know how Tweedy’s pleas that “You have to learn how to die / If you want to be alive” amidst radio fuzz and carefully crafted soundscapes makes me feel. Maybe it was written as a cryptic anti-war ballad, but for me it’s a celebration of life, three minutes and 51 seconds of joy that never grows old. —Josh Jackson

17. “Forget the Flowers”
After the sloppy-barroom-country vibe of Wilco’s debut, A.M., the band returned with a wider focus and a tighter groove on Being There. “Forget the Flowers” was right in both those lanes, with a jumpy chord structure that sounds simpler than it is, a classic Tweedy lyric (melancholy but tongue-in-cheek, about a guy who coldly dumps his gal and comes to regret it), and vastly improved instrumentation, thanks in part to new member Jay Bennett and his pedal steel. Echoes of the Stones’ deadpan country classic, “Dead Flowers,” showed a young band swinging for the fences. —Matthew Oshinsky

16. “Poor Places”
In another time, “Poor Places” could’ve been fine fodder for arena pop rock. The way the anthemic piano chords meet the politely distorted guitar in a warm, enveloping crescendo during the first third of the song wouldn’t sound unusual in a Snow Patrol song. But what elevates Yankee Hotel Foxtrot’s 11 o’clock number is the way the song craters in on itself. The band swamps out instrumental moods and pits small, delicate riffs against each other, leaving listeners both comforted and cornered. Tweedy’s verses bristle and wither with incoherent observations that disjointedly illustrate the disconnect between how people love versus how they want to be loved. The song’s slow implosion over a mesh of static, as Tweedy chants, “I’m not going outside,” is one of Wilco’s most hollowing moments. —Zane Warman

15. “Box Full of Letters”
Another gem from Wilco’s stunning debut A.M., “Box Full of Letters” followed the same rootsy template established by their forbearer Uncle Tupelo, with a loping, bittersweet mid tempo rocker spun with homegrown sentiment, tattered emotion and unabashed honesty. An unlikely break-up song, it finds Tweedy questioning his lover’s reasons for leaving while also expressing confidence she’ll return, even if only to be a friend. An early example of the band’s signature sound before they drifted into experimental realms, it typified the new alt-country crossover approach Wilco championed early on. —Lee Zimmerman

14. “I’m The Man Who Loves You”
“I’m the Man Who Loves You” plays like two very distinct halves. The first shows a man nervous to make his true feelings known. But the second half, which comes after booming horns and a monotone guitar solo, has Tweedy returning to his same feelings, but this time around with a sense of triumph, as if he’s finally made the leap of admitting how he feels. “I’m the Man Who Loves You” is a rare Yankee Hotel Foxtrot song of joyous proclamations, filled with love and uncertainty, but reveling in the possibilities of putting yourself out there. —Ross Bonaime

13. “Muzzle of Bees”
In Wilco’s native Chicago, unexpected summer thunderstorms are commonplace. The A Ghost Is Born highlight, “Muzzle of Bees,” is the musical equivalent of this weather phenomenon—torrential downpours of distorted electric guitars interrupting what could be the most tranquil acoustic landscape Jeff Tweedy has ever imagined. The band utilizes this dynamic to its fullest, describing the feeling of falling in love with someone and thinking that everything around him is positive before thoughts of self-doubt creep into his head. “And dogs laugh, some say they’re barking / I don’t think they’re mean,” Tweedy croons over a peaceful acoustic guitar. But that all changes when the thought of that love not being reciprocated and the thunderstorm hits, prompting the guitar freak-out to come out of nowhere: “I’m assuming you love me / And you know what that means.” By the end, the tempest seems to reach a resolve, but after its big crescendo, Tweedy is soaked from the rain. —Steven Edelstone

12. “Hummingbird”
An unusually jaunty rhythm underscores the apparent sadness of “Hummingbird.” The lyrics are poetic but ambiguous, describing a man whose “goal in life was to be an echo, riding alone, town after town, toll after toll, a fixed bayonet through the great southwest to forget her.” Ultimately, he seeks solace in the hope she’ll remember to remember him, a faint echo of a distant past, as striking and sublime as a hummingbird flapping its wings. Few songs sung about tattered love have ever come across as expressive, and yet as fleeting, at the same time. —Lee Zimmerman

11. “How to Fight Loneliness”
Wilco’s Summerteeth is arguably the record that pushed their sound from established alt-country to complex folk rock with emotional depth. “How to Fight Loneliness” best encapsulates that with consistent, sensational melodies, and layered arrangements that make light use of Latin rhythms. The lyrics are straightforward, but cutting, as Tweedy sings, “How to fight loneliness / Smile all the time / Shine your teeth ‘til meaningless / Sharpen them with lies.” Still, smiling all the time doesn’t always combat the tough times. —Samantha Lopez

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