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

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