The 30 Best Wilco Songs

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

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The 30 Best Wilco Songs

After more than two decades, we’re pretty convinced that Wilco can do no wrong. We featured a Wilco song way back in the day on our first-ever CD sampler, and our love for the Chicago alt-country pioneers has continued ever since, whether for their pop irreverence or serious experimental compositions.

The band’s reach has only grown over the course of its 10 studio albums (of wholly original compositions). Of course, in addition to Wilco-specific projects, its members have branched out to other musical endeavors, as well. Tweedy kickstarted Mavis Staples’s resurgence and started an eponymous band with his son. Multi-instrumentalist Pat Sansone and bassist John Stirratt played in The Autumn Defense, and Sansone has collaborated with bands like Radiohead and Dawes. Drummer/composer Glenn Kotche has worked with So Percussion and Kronos Quartet (not to mention a kitchen sink in a Delta faucet commercial), and Nels Cline, one of the finest guitarists of his generation, has released a range of solo records. But now, in the days since the release of Tweedy’s latest solo effort, Together at Last (you can read our review here and watch Tweedy play a solo version of “I Am Trying to Break Your Heart” here), we’re sifting through Wilco’s studio albums and side projects, from 1995’s A.M. to last year’s Schmilco, to find their 30 best songs.

30. “Just Say Goodbye”

Schmilco’s closing track is a solemn bookend to Wilco’s stalwart 10th effort from 2016. Although the record as a whole can feel tired at times, it maintains the inherent beauty of a Wilco record. In particular, “Just Say Goodbye” stands as a bright spot thanks to Tweedy’s hushed vocals, Glenn Kotche’s lovely drumming and Nels Cline’s effortless, clean guitar parts. —Adrian Spinelli

29. “Random Name Generator”

Wilco was full of surprises in 2015: They released an album over the summer without notice, named it Star Wars and gave it away for free, just for the hell of it. Nice. They also staked a persuasive claim on a permanent spot in your cerebral cortex with “Random Name Generator,” a song so relentlessly catchy that it may never stop bouncing around in there. Layers of fuzzed-over guitar tumble through the riff while singer Jeff Tweedy plays with the feel of the words in the title, chanting them, stretching them and rolling them around in his mouth like he’s savoring every syllable. And why wouldn’t he? It’s the standout track on an album built for fun. “What’s more fun than a surprise?” Tweedy asked that July. Not much, when it’s a surprise this good. —Eric R. Danton

28. “Passenger Side”

Written in the aftermath of Uncle Tupelo’s bitter break-up, and included on the band’s debut album A.M., “Passenger Side” sounds like a mournful ode to old times. “Roll another number for the road / You’re the only sober person I know,” Tweedy sings with a reflection and remorse that includes a plea for continued companionship and a steady hand to help guide him forward. Lovely, plaintive and slightly anguished, it’s a song that suggests an uncertainty of starting from scratch, leaving the past behind and taking an unknowing step toward the future. —Lee Zimmerman

27. “Art of Almost”

Over the past several years and handful of Wilco albums, some have cast a little doubt on the Chicago sextet’s musical direction and fade into a relative sense of complacency. Jeff Tweedy disproves any such doubts, recapturing our attention at a moment’s notice. “Art of Almost,” the intricate seven-plus minute album opener to 2011’s The Whole Love, is standing proof that the generational rock group can seemingly do whatever it wants whenever it wants.—Max Blau

26. “Please Be Patient With Me”

Tweedy has never shied from sharing about his chronic migraines and old addictions, but this acoustic ballad from Sky Blue Sky is a prayer and a plea for when he works through periods of being unwell. In fact, he doesn’t so much ask, as tell listeners, “I’m gonna need you to be patient with me,” drawing out the “need” for extra emphasis. With three verses sung in three minutes, simplicity is this song’s biggest boon. —Hilary Saunders

25. “You & I”

“You and I” was the first duet to ever be featured on a Wilco album and collaborating with Leslie Feist was a strong choice. Both artists were coming off triumphant albums (Sky Blue Sky for Wilco and The Reminder for Feist) and this was a major bright spot on the tragically-titled Wilco (The Album). While the album ultimately stands as the beginning of Wilco’s slow descent from one of music’s most memorable six album runs, this collaboration with Feist vaulted the band into a slow ascent into the mainstream pop conversation that they’ll remain in forever. —Adrian Spinelli

24. “Outtasite (Outta Mind)”

One of Wilco’s most commercially successful singles, “Outtasite (Outta Mind)” is a fun listen when most of the Chicago outfit’s songs are not. While the lyrics don’t necessarily reflect the upbeat alt-country rock behind Tweedy’s voice, it’s easy to get lost in the foot stomping, fist-in-the-air guitar riffs and driving drumbeats. Nowhere is that contrast more evident is in the song’s music video, portraying the band smiling while playing their instruments as they skydive out of an airplane. —Steven Edelstone

23. “California Stars”

In 1998, WIlco joined British punk cowboy Billy Bragg to compose music for a batch of unreleased Woody Guthrie lyrics, provided by Guthrie’s daughter, Nora. “California Stars,” one of seven Wilco tunes (literally) on the record, takes a sweet-natured approach to the material, pairing an unrequited wish to quit working and live free in California with an equally simple and earnest song. As with many Wilco songs, the power is in Tweedy’s moldered voice, weary yet whimsical and a seamless fit for the tales of Guthrie’s dust-bowl dreamers, always pushing west toward paradise, but never quite finding it. —Matthew Oshinsky

22. “I’m Always in Love”

Wilco goes power pop on “I’m Always in Love,” a standout from Being There and an enduring fan favorite. From the big, simple riff, the minor-chord twists, and the synthesizer constantly humming over it all, this should’ve been a radio staple in the spring of 1999. —Garrett Martin

21. “Why Would You Wanna Live”

Another giant leap forward on Being There, “Why Would You Wanna Live” takes all the country fixins—banjo, fiddle, slide guitar, piano—and cleverly polishes them into an existential minor-chord odyssey. “Why,” Tweedy sings, “Would you wanna live in this world?” A gentle but persistent piano march gives way to a lilting, half-tempo chorus and bounces back again, with guitarist Jay Bennett and banjoist Max Johnston adding gorgeous flourishes that feel both vintage and new. That magic formula would be Wilco’s calling card from Being There forward. —Matthew Oshinsky

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

10. “Pot Kettle Black”

Named for its eponymous epithet, “Pot Kettle Black” is a driving four-minute groove from Yankee Hotel Foxtrot. Like the saying goes, Tweedy calls himself out for criticizing other people for the same things that he’s guilty of doing. But by doing so, he obviously exonerates himself. It’s a tongue-in-cheek critique of being hypocritically judgmental, but allowing oneself to smile upon that realization. —Adrian Spinelli

9. “At Least That’s What You Said”

As the opening track to 2004’s A Ghost Is Born, “At Least That’s What You Said” almost comes off like it could be either the intro to the events of their previous album Yankee Hotel Foxtrot’s “I Am Trying To Break Your Heart,” or maybe the regretful hangover. Tweedy’s somber vocals are turning panicked accompanied by slammed pianos and spastic guitar solos. The dreamy tone to “At Least That’s What You Said” sets up the experience of the whole record nicely—a strange, heartfelt beginning that shows the band’s full-on experimentation and honing of their newfound penchant for unusual combinations of styles and sounds. —Ross Bonaime

8. “Impossible Germany”

This is Nels Cline’s crowning moment as Wilco’s lead guitarist. Not only that, but this is the moment when it became clear that Cline was the right choice to move forward with the band and he’s remained with them since he first appeared on Sky Blue Sky in 2007. “Impossible Germany” is a staple at Wilco shows, namely because of just how silky Cline’s work is. Credit to Tweedy for writing an incredible song that addresses the expectations within a grounded relationship, juxtaposed with how America felt about our place in the world in the pre-WWII era. —Adrian Spinelli

7. “Hate It Here”

No one has ever sounded so agonized about checking the mail than Tweedy on “Hate It Here.” A cut from 2007’s Sky Blue Sky, in which guitarist Nels Cline has never shined brighter, “Hate It Here” features his velvet tones morphing into jagged wails and back again. Tweedy sings about homebody minutia—cutting the grass, doing the laundry, checking the phone and the mail for messages—waiting for his lover to return until he screams, “I hate it here,” pausing for a stomp, “when you’re gone.” And it’s true: You can really start to hate a place you love when the person you love is gone. —Hilary Saunders

6. “Via Chicago”

Despite its ominous opening lines (“I dreamed about killing you again last night / And it felt alright to me”), “Via Chicago” immediately unfolds as a tender ode to the city that gave the band their start. Culled from the album Summerteeth, it’s bathed in wistful reflection, but ultimately comes across as another in a long line of Wilco escape songs, an expression of passive acceptance that finds resolution simply by returning to the place where comfort was found early on. The passive melody is eventually entangled in dissidence that surfaces and then fades as the song works its way to an otherwise unobtrusive exit. Even so, it remains one of the band’s most elegiac entries. —Lee Zimmerman

5. “She’s a Jar”

Throughout Wilco’s entire career, Jeff Tweedy uses outlandish imagery to convey the complexity and randomness that stems from loving someone, and “She’s a Jar” may represent the most surreal, yet straightforward. “She’s a jar with a heavy lid” is one of Tweedy’s best metaphors to date; like opening a container that just won’t budge no matter how much muscle you put into it, the mysterious “she” won’t let Tweedy in on her deepest secrets. Over a hypnotic drum beat with sleepy harmonica and keyboard interludes, Tweedy struggles to make sense of his relationship becoming frustrated to the point where his partner has to beg him not to hit her because of their mutual inability to tell, not show. —Steven Edelstone

4. “A Shot in the Arm”

Although it originally appeared on Summerteeth, the Kicking Television version of “A Shot in the Arm” offers a more raucous take on an already emotionally and musically raw song. The guitars quake louder in the intro and Tweedy’s vocals quiver less in the closing admission, “What you once were isn’t what you want to be anymore.” But the song really relishes in its rock ‘n’ roll crescendo when Tweedy screams, “Maybe all I need is a shot in the arm / something in my veins / bloodier than blood” over and over again until he’s exhausted himself like a child ready to succumb to blessed rest. —Hilary Saunders

3. “Jesus, Etc.”

Tweedy is a master of American vernacular and on “Jesus, etc.”, he captures the way we speak to each other when the doors are closed and no one else is around. The way he describes a building’s sway for a breath, effectively evoking the feel of Chicago’s Marina Towers which grace the cover of Yankee Hotel Foxtrot is beautiful. And yet, for all of Tweedy’s immaculate lyrics, the orchestral arrangement of “Jesus, Etc.”—with a humble string section, John Stiratt’s perfect bass line, Glenn Kotche pacing the drums in the background and the late great Jay Bennett on lap steel—make this the most memorable song on one of the greatest albums in American history. —Adrian Spinelli

2. “Misunderstood”

The lead-off track on Wilco’s sophomore record, the sprawling double-disc Being There, “Misunderstood” made it abundantly clear that Wilco had much more to offer than the garage tunes of of A.M and Tweedy’s previous band, Uncle Tupelo. With its noisy, ominous intro and long, cacophonous ending that sounds like the song collapsing on itself, “Misunderstood” foreshadows the experimentation that would define Yankee Hotel Foxtrot five years later. But it shouldn’t be viewed solely as a stepping stone to better music: It’s a wistful, melancholy epic bidding good night to the rock ‘n’ roll era, with Tweedy essentially offering his artist credo: “There’s a fortune inside your head / All you touch turns to lead / You think you might just crawl back in bed / You’re so misunderstood.” —Garrett Martin

1. “I Am Trying to Break Your Heart”

With a song like “I Am Trying to Break Your Heart,” it’s almost understandable why the band’s then-label, Reprise, wouldn’t be happy with the massive change in the band’s sound. “I Am Trying to Break Your Heart” is a disorienting cavalcade of instruments, from scratching strings to inebriated pianos. This sound of chaos perfectly matches the drunken ramblings of Jeff Tweedy as narrator, whose mood swings and heartbreak bring about misplaced confidence and sorrow found in regrettable memories. Tweedy constantly comes back to the line “what was I thinking,” and the entire band similarly seems to be on different wavelengths, each in his own stupor, until they coalesce into one sound for only a few beautiful moments before swerving back into frantic confusion. The seven-minute masterpiece is a staggering accomplishment for the band that somehow finds synchronicity in its insanity and proclaims a completely new era for Wilco going forward. —Ross Bonaime