The Story Behind Wilco’s ‘Yankee Hotel Foxtrot’—the Album So Nice, They Got Their Label to Pay for It Twice

There are many ways Yankee Hotel Foxtrot could have failed. Wilco could have imploded and never released their fourth album. Or they might have released one of the many permutations of the album to lackluster reviews and continued touring medium-sized clubs—never becoming one of the most revered bands in America. Thankfully, that’s not the way things turned out. 

So how did Yankee Hotel Foxtrot happen? How did the band famously make Warner/Reprise pay for the album twice? What’s the story behind Wilco’s defining album? Yankee Hotel Foxtrot is a classic tale of art colliding with commerce. Wilco’s label refused to release the album. Then it became the band’s best-selling work. 

The album and its history are paradoxical. Foxtrot sounds both intimate and colossal. It sounds both familiar and groundbreaking. Looking back on the album, Wilco’s Jeff Tweedy told the New York Times, “I was trying to put it in perspective for myself: How can there be all these good things that I love about America, alongside all of these things that I’m ashamed of. And that was an internal question, too; I think I felt that way about myself.”

Sam Jones’ well-known 2002 documentary, I Am Trying to Break Your Heart: A Film About Wilco, tells the story of Yankee Hotel Foxtrot. Bandmates Jeff Tweedy and virtuoso multi-instrumentalist Jay Bennett, each struggling with addiction, battled one another for creative control of the album. Tweedy brought in experimental producer Jim O’Rourke to help him finish the album. 

Around this time, Tweedy became obsessed with a collection of shortwave radio recordings called The Conet Project. Believed to be spy transmissions, one track features an ominous female voice: Yankee. Hotel. Foxtrot.

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Tweedy and O’Rourke had a side project called Loose Fur. O’Rourke introduced Tweedy to drummer Glenn Kotche, who played in Loose Fur. By this point, Wilco had already recorded their fourth album. But Tweedy was creatively frustrated and unhappy with the album’s direction, including Ken Coomer’s drum parts. Kotche was brought in to re-record Coomer’s parts. The additions of O’Rourke and Kotche would eventually lead to Coomer’s exit in 2001. Tweedy’s pull toward the avant-garde was too strong. Beginning with Wilco’s second album, Being There, he had outgrown the limitations and clichés of the alt-country genre he is said to have had a hand in creating. 

Tweedy secretly asked O’Rourke to mix “I Am Trying to Break Your Heart.” The band was impressed with his mixes, but this only added tension with Bennett, who wanted to mix the album himself. Tweedy and Bennett continued to argue over the album’s direction. Tensions increased further when O’Rourke cut the other band members’ contributions out of some songs. These recordings left some tracks recorded by only Tweedy, O’Rourke, and Kotche. Thus, Wilco had essentially become Loose Fur.

So Wilco not only rebuilt the songs on Foxtrot, but they also rebuilt the band. Bennett, an important part of Wilco’s evolution, was cut loose shortly after the album was completed. He died in 2009 after being given a flawed fentanyl patch by doctors to help ease pain before hip surgery. A documentary called Where Are You, Jay Bennett? was released in 2021 (the full version’s available on YouTube right here). 

When the album was presented to Warner/Reprise, the label gave them that classic, often short-sighted major-label response: they felt there wasn’t a single. So they rejected Foxtrot and Wilco was released from their contract. The band’s manager, Tony Margherita, negotiated Wilco’s ownership of the album’s master tapes when they left. 

Several new labels wanted the band, and Wilco signed with Nonesuch Records, a subsidiary of Warner. In poetic irony, Warner paid for Yankee Hotel Foxtrot twice. Released in 2002, the album reached No. 13 on the Billboard 200, becoming Wilco’s highest-charting album yet. Widely acclaimed by critics and fans alike, it remains Wilco’s best-selling record as of this writing. 

[AS OF THIS WRITING: Wilco Tickets Are Available! – Get ‘Em Right Here]

To celebrate the 20th anniversary of Yankee Hotel Foxtrot, a deluxe reissue featuring early versions of the songs was released in 2022. It won a Grammy Award for Best Historical Album and provides a fascinating look at the evolution of Wilco’s masterpiece. It’s a peek inside the myriad ways the album could have turned out, showing how the songs were disassembled and rebuilt during a period of tumult for the band. It was the album that nearly destroyed Wilco. Then it saved their career.

Art, like the world, is messy. It can fall apart at any time. The fragile and ephemeral nature of things is often profoundly sad. Like Yankee Hotel Foxtrot, it can also be beautiful.

I am trying to break your heart
I am trying to break your heart
But still, I’d be lying if I said it wasn’t easy
I am trying to break your heart

Photo by Jason Merritt/FilmMagic for Superfly Presents