Five essential Wilco songs that guitar players need to hear

It’s hard to get into Wilco partly because they’ve made it hard – beyond the size and scope of their catalogue, they’re the sort of band who’d make a whole record to prove you wrong if you said they sounded a certain way. It’s maddening but also consistently surprising, grumpy, scruffy fun.

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Formed in Chicago 30 years ago following the dissolution of the rollicking alt-country band Uncle Tupelo, Wilco have been led down any number of rabbit holes by guitarist-vocalist Jeff Tweedy and bassist John Stirratt, the only surviving members from a first decade that had a revolving door vibe to it. In 2004, with the arrival of guitarist Nels Cline and keyboard player Pat Sansone, though, they settled into a line up that has remained reliable even while continuing to chase down different sounds album to album.

Across 13 LPs Wilco have written wistful pop songs, mean-spirited jams, trad country weepies and open-ended rock epics that have been adored, derided and debated with equal fervour by cooler-than-thou critics and people who have a favourite model of New Balance shoes. In that spirit, here are five songs to get you started that you will almost certainly disagree with once you’ve picked the top layer of varnish off the band’s discography.

Start Here: I Am Trying to Break Your Heart (Yankee Hotel Foxtrot, 2001)

An obvious pick for the heads, but maybe a necessary one for what it says about Wilco’s approach to pop music, which seems to come from a place of reverence one minute and disgust the next. Yankee Hotel Foxtrot is their most famous record – you know the album sleeve, perhaps something about its groundbreaking digital release after their label Reprise got cold feet – and also their masterpiece.

It’s nebulous, confrontational, experimental, but also firmly grounded in the mechanics of lean, melody-forward writing. Propelled by new drummer Glenn Kotche’s freeform approach this is a loping, strange song that’s also the catchiest thing you’ve heard today. Its guitars are like macaroni pieces stuck to a sheet of paper – they stick out as textures, from acoustic strumming to feedback and washes of static that act as auxiliary percussion.

Then Go Here: Can’t Stand It (Summerteeth, 1999)

Before they took a hammer to it with Yankee Hotel Foxtrot, Summerteeth’s gleaming pop-rock style felt like Wilco finding their feet and, potentially, somewhere to put down roots. It excised them from the alt-country scene that they’d existed amid since the Uncle Tupelo days, with its sleek staging at odds with their formative rough and tumble. Here they delved into the mini pop symphonies of the 1960s, serving up songs where the bells and whistles weren’t beside the point, they kind of were the point.

But, true to that mode, they were miserable while doing it, assuming that everything was just going to collapse. On the opener Can’t Stand It this sense of doomed grandiosity is beautifully illustrated by the chorus drop’s literal bells, which are followed by the timeless simplicity of its guitar and vocal melodies. They cut through the wall of sound, suddenly out there alone. “You know it’s all beginning to feel like it’s ending,” Tweedy sings. “No love’s as random as God’s love. I can’t stand it.”

Stop Off Here: Impossible Germany (Sky Blue Sky, 2007)

If you were writing a movie script, Cline’s first record with Wilco would have been Yankee Hotel Foxtrot. From a vibe perspective it makes perfect sense. A jazz-reared Thurston Moore collaborator would have been at home there, more so than on the woolly Sky Blue Sky, a record Pitchfork’s Rob Mitchum believed “nakedly exposes the dad-rock gene Wilco has always carried but courageously attempted to disguise.” Now, that’s essentially true. It’s just that it’s not necessarily that deep of a burn.

Amid these sedate, considered songs, Cline gets way out there on Side With the Seeds, blowing a proggy hole through its crushed velvet chest, and loses himself in Impossible Germany, spinning off into something that has often been observed to resemble Television’s twin-guitar voyages. Given the fact that Moore bought his first Jazzmaster because Tom Verlaine played one, maybe this leap isn’t as big as it initially appeared.

Almost Home: At Least That’s What You Said (A Ghost is Born, 2004)

Please welcome a different guitar weirdo into the equation: Jim O’Rourke. Having mixed Yankee Hotel Foxtrot, he stepped up to produce its follow up. A Ghost is Born found Tweedy pushing further into the outer reaches of Wilco’s sound, with songs that sprawled to marathon lengths and bled over genre borders. It would be easy to pick Spiders (Kidsmoke), where O’Rourke decorates its motorik pulse with a barely legible scrawl of notes, here but instead it’s interesting to note the lengths to which Tweedy himself goes on At Least That’s What You Said, thrashing and wailing through solos that put roiling water between its closing sections and its measured opening. There is something decidedly War on Drugsy about its denouement, bringing dad-rock back into the chat and posing an interesting question about what’s cool and when.

Nightcap: Ten Dead (Cousin, 2023)

At a time when Wilco might have fully surrendered to age and complacency, their most recent record found them calling on outside help to break apart their methods all over again. This time around it was Cate Le Bon in the role of disruptor-in-chief, with the Welsh psych-pop great intent on foregrounding the sense of restlessness that underpinned the band’s best work. Halfway through Ten Dead it’s tempting to vacate the planet in the company of Cline, who finds a pocket of spaced-out bliss for a solo that is brilliantly punctured by Tweedy’s sad-sack delivery of lyrics that recount dead-eyed American indifference to mass shootings. “I woke up this morning and I went back to bed,” he sings. “Ten dead, ten dead.”

Where next?

Uncle Tupelo makes sense as a starting point, particularly given the hangover from those days that Wilco carried around in their earliest work. There is a tendency to want to focus on their curveballs – see also collaborative records with Billy Bragg or The Minus 5 – but even in their more prosaic pop-rock output Wilco are a serious band, with gravitas and wit to match gilt-edged melody. Why not chase a Schmilco cut with something wild from Cline’s backstory while reading Tweedy’s excellent autobiography? Cover every base.